NIST Heat Combution Data Book

RP41
HEATS OF COMBUSTION OF ORGANIC COMPOUNDS

By M.
S.
Kharasch
ABSTRACT
The literature on the heats of combustion of organic compounds is critically
A table of "best" values for this constant has been compiled covering
reviewed.
all available information on record in the literature.
A method for calculating the heat of combustion from the structural formula
of the compound is described, and the values calculated according to this method
are tabulated for comparison with the observed values.
The comparison demonstrates that the calculated values are sufficiently

The difference between calculated and
accurate for most practical purposes.
observed values seldom exceeds 1 to 2 per cent except in cases where there is
reason to doubt the accuracy of the observed value. In most cases the two
values agree within the accuracy of the observed value.
CONTENTS
Page
I.
II.
III.
Introduction
Standards for combustion calorimetry
Choice of data
Abbreviations, units, and conventions
Calculation of heat of combustion
Structural correction factors
359
362
363
363
364
366
370
370
IV.
V.
VI.
VII. Index of compounds, by classes
3.
CH compounds
CHO compounds
N compounds
4.
Halogen and sulphur compounds
1.
2.
371
371
372
VIII. Tables of data
373
421
426
IX. Bibliography
X. Index of compounds, by formula
I.
INTRODUCTION
In the present collection of the data od the heats of combustion of

made to select the best
available value for each compound.
The work has been particularly
organic compounds, an attempt has been
difficult because only a few authors give the necessary information

concerning the unit of heat and the thermochemical corrections used,
and without this information it is impossible to bring the values to a
common
basis.
The thermochemical data recorded in the tables have been obtained

by the use of the following thermochemical methods: (1) The universal-burner method, (2) the
3697 29
1
bomb method.
359
360
Bureau of Standards Journal
of Research
[voi.g
" universal-burner " method, in the hands of Thomsen, gave
The
results
which agreed on the average to not better than 0.5 per cent.
Owing
to the design of his apparatus,
to substances easily volatile at
it is
applicable only to gases or
room temperature, and
his values are
be trusted only to the extent to which this condition was realized.

This seems to be the consensus of opinion of most workers in thermochemistry. It is, however, necessary to apply two corrections to his
values in order to bring them into accord with modern determinations.
Both of these corrections are negative. The first one (0.3
per cent) corrects his thermometer readings to the hydrogen scale,
and the second one ( 0.1 per cent) corrects for the new determinaOnly the values so corrected are
tions of the heat capacity of water.
recorded in the tables.
The " bomb-calorimeter" method was first used by Andrews in
1848, the determinations being carried out at a pressure of one
atmosphere. In 1883 Berthelot reintroduced the method and improved it considerably. The combustions by this improved method
were carried out with oxygen under pressure. The details of the technic have since undergone revolutionary revisions.
For particulars
the reader is referred to the articles of Richards and his collaborators;
Roth and collaborators; Dickinson, Verkade, and collaborators; and
Swietoslawski and collaborators.
Of the four different procedures that have been proposed for the
measurement of heats of combustion by means of a calorimetric
bomb, only two have attained considerable use. 2 These are known
as the " ordinary" or "common" method and the "adiabatic"
method. In the "common" method the rise of temperature of the
calorimeter is observed while the "jacket" temperature is kept
constant.
In the "adiabatic" method the temperature of the
"jacket" is kept the same as the temperature of the calorimeter and
only the initial and final temperatures measured. This latter method
may be called the "American adiabatic" method, for it was first proposed by S. W. Holman 3 and refined thoroughly by Richards and his
It has been used extensively only in the United
collaborators.
to
States.
It should be stated at this point that the results of the
two methods
agree within the limits of experimental error. 4

i
3
4
Andrews, Pogg. Ann.,
75, p. 27; 1848.
The other two methods are those of Hosehus and

S. W. Holman, Proc. Am. Acad., 31, p. 252; 1895.
Dickinson, Bull. Bureau of Standards,
p. 725; 1923.
Fery.
11, p. 243; 1915;
Schlapfer and Fioroni, Helv. chim. Acta,
6.
ziiarasch)
Heats of Combustion of Organic Compounds
The method
of calibrating the calorimetric
system
The methods which have been
importance. 6
is
361
of the greatest
at times
employed by
the investigators and pertain to the values recorded are as follows:

(1) Calibration by the electrical method; (2) thermal calibration;
the additive calibration.

The electrical calibration consists in supplying electrically a
(3)
1.
of energy to the calorimeter and measuring the

temperature rise. The results of such observations give directly the
heat capacity of the calorimeter and its contents in joules per degree.
The value in calories is then obtained by dividing by the mechanical
equivalent of heat. This method forms the basis of the work of
Fischer and Wrede; Wrede, Jaeger, and von Stein wehr; Dickinson,
Roth, Swartz, Moureu, and Andre. The work of these investigators
is very thorough and of a high order of accuracy.
2. In the thermal method of calibration a standard substance of
known heat of combustion is burned in the calorimeter. Where the
other calorimetric measurements have been properly carried out this
method, using one of the standard substances mentioned below, yields
measured amount
reliable results.
In the additive-calibration method the heat capacity of the

is obtained by adding together the heat capacities of its
This method has been used extensively by some French and
parts.
some Russian investigators. While the work has been carried out
with a great deal of zeal, yet essential details of procedure are often
3.
calorimeter
entirely lacking
and
it
is
thus usually impossible to compare the

These statements apply to work
values with those of other workers.

of Berthelot
and
Louguinine, Zubov, and a number

Recently the values of Zubov's work have
his collaborators,
of other investigators.
been put upon a better basis by Swietoslawski, to whom Zubov

turned over most of his experimental material. From the method
5
The
following are
some
of the
most important references dealing with the calibration
of the calorimetric
system:
1.
Bestimmung des Wasserwertes eines Berthelot'schen Kalorimeter in elektrischen Einheiten, W.

und H. von Steinwehr, Verhandl. Deutsch. Phys. Ges., 5, p. 50; 1903; and 5, p. 353; 1903.
Jaeger
2. Concerning the adiabatic determination of the heat of combusion of organic substances, Richards,
Henderson and Frevert, Proc. Am. Acad., 42, p. 573; 1907.
3. Beitrag zur kalorimetrischen Messung von Verbrennungswarme, W. Jaeger and H. von Steinwehr,
Zs. f. Phys. Chem., 53, p. 153; 1905.
4. Eichung eines Berthelot'schen Verbrennungskalorimeters in elektrischen Einheiten mittels des
Platinthermometers, W. Jaeger and H. von Steinwehr, Ann. d. Phys. (4), 21, p. 23; 1906.
5. Ueber die Korrektur fur die Warmestrahlung bei Kalorimetrischen Versuchen, A. Schukarew, Zs. f.
Phys. Chem., 56, p. 453; 1906.
6.
7.
8.
9.
An
accurate Calorimeter, White, Phys. Rev., 25, p. 137; 1907.
Eichung des Verbrennungs kalorimeter und Arbeitsweise, Roth, Lieb. Ann., 373, p. 249; 1910.
Lag effect and other errors of calorimetry, White, Phys. Rev., 31, p. 562; 1910.
A calorimetric arrangement for the new bomb, Phillippe Landrieu, Bull. Soc. Chim.,-37, p. 1340;
1925.
362
Bureau
of Standards Journal of Research
[voi,s
employed by Swietoslawski in correcting Zubov's data, it is evident

that Zubov applied most tliermometric corrections, except that the
heat capacity of his calorimetric system has been erroneously determined. These recalculated values of Zubov are in better agreement
with more modern values and are the ones recorded in the tables.
II.
STANDARDS FOR COMBUSTION CALORIMETRY
Of the three substances which have been used
in the past as stand-
shown by recent
At
Pure and Applied
ards in combustion calorimetry, only one has been

researches to
meet the requirements
a primary standard.
of
the third conference of the International
Union
of
Chemistry held at Lyons, 6 benzoic acid was adopted as the primary

standard. The value chosen for its heat of combustion was the
one found by Dickinson, 7 namely, 6,324 g-cali 5 per gram in air or
6,319 g-calis per gram in vacuo. 8 It is more or less tacitly assumed
that the above value holds for an isothermal heat of combustion in
the neighborhood of 20. 9 When converted into absolute joules
these values become 26,466 and 26,445, respectively.
Dickinson's
value was obtained by absolute electrical standardization of his
calorimetric system, and the measurements were carried out by the
ordinary as well as the adiabatic method.
It is of importance to note here the determinations which have
been made of the ratios of the heats of combustion of benzoic acid,
naphthalene, and cane sugar. For these determinations Richards
and his collaborators employed only the adiabatic method, Verkade
and his collaborators the ordinary method, while Swietoslawski and
his collaborators and Schlapfer and Fioroni employed both the
adiabatic and ordinary methods. These ratios, as summed up by
Schlapfer and Fioroni as a result of a very thorough investigation
both by the ordinary and the adiabatic methods, are:
Naphthalene ^ 1.5201 Benzoic acid = 1.6028 Naphthalene == 2.4364
Benzoic acid
(air)
Sucrose
(air)
Sucrose
(air)
These ratios are quite similar to those obtained by Dickinson and

by Verkade and Coops, jr. 10
Secondary Stand ardsRecently Verkade and Coops, jr. 11 have
suggested salicylic acid as a secondary standard. Their suggestion,
backed by a large amount of information, certainly merits consideraGermany was not
?
represented at that conference.
Bull. Bur. of Standards, 11, p. 243; 1915.
See W. Swietoslawski's defense of this value, J. Chim. Phys., 22, p. 583; 1925; and P. E. Verkade and
Coops, Z. Physik. Chem., 118, p. 123; 1925.
See Rec. Trav. Chim., 44, p. 800; 1925, for the temperature coefficient of the heats of combustion of
benzoic and salicylic acids.
w P. E. Verkade and Coops, jr., Rec. Trav. Chim., 42, p. 223; 1923.
ii P. E. Verkade and Coops,
Note also the discussion by Swietos jr., Rec. Tr. Chim., 43, p. 561; 1924.
lawski upon the establishment of such a secondary standard, Bull. Soc. Chim. (4), 37, p. 84; 1925.
*
J.
Kharasch]
tion.
The value
gators
is
recommended by these investiper gram in air and 5,238 g-cal 15 per gram
5,242X4.185 = 22,699 and 5,238X4.185 = 21,921
for salicylic acid
5,242 g-cal
in vacuo, that
363
is,
i5
absolute joules, respectively.

III.
CHOICE OF DATA
Since in the tables below only one value
is as a rule given for each

has been necessary to exercise a certain amount of
arbitrariness in the choice, but whenever possible the opinions of all
workers in thermochemistry, as expressed in their articles, have
been taken into account. Naturally, where an author has described
compound,
it
method
method has been
carefully his
his
of procedure, corrections used, etc., or

sufficiently well established,
his values
where
were
who merely recorded the

The names of all the investigators
who have determined the heats of combustion of each compound
are, however, recorded.
When only one value for a compound is
given preference over those of an author
heats of combustion obtained.
quoted, irrespective of whether or not the value is very reliable, it

has been thought desirable to make available even this approximate
On the whole, for the guidance of the users of the tables,

be stated that the work of many of the French investigators
is not in complete agreement with the best modern determinations.
The values are on the whole rather high, but no factor can be employed to correct them, for the variations from author to author are
too large. However, the maximum error in most cases is not larger
than from 1 to 1.5 per cent.
Preference has been given also to Thomsen's values for gases and
for easily volatile compounds over those of Berthelot and his collaborators.
The order, however, was reversed for difficultly volatile
substances, for Thomsen's values for such compounds are too high.
result.
may
it
IV.
ABBREVIATIONS, UNITS, AND CONVENTIONS
Unit Employed.
in
The heats
absolute kilo joules
(at
of combustion recorded are expressed

constant pressure) per gram molecular
weight of substance in vacuo. Where the investigators indicated the

unit of heat employed by them that unit of heat was multiplied by
the proper factor to convert the value into absolute kilo joules, otherwise the 18 calorie was assumed to have been used. 12
Vacuum Correction. The vacuum correction in very few cases
amounts to more than 0.13 to 0.16 per cent. It is quite evident,
therefore, that where the accuracy of the method, experimental procedure, and corrections used apparently introduced a much larger
error, such a correction is of very little consequence as far as the
12
The
factors
used to convert into joules were the ones adopted by the International Critical Tables.
364
Bureau
[voi.s
However, it was felt

and for that reason
the values of the investigators have been corrected ad vacuum whenever there seemed the slightest justification for it and when the specific gravity of the substances was known.
Of the investigators who
have done considerable work in thermochemistry and whose results
were sufficiently accurate to merit this correction, we might mention
Stohmann and collaborators; Zubov, 13 Koth, Fischer and Wrede;
Wrede, Dickinson, Kichards and collaborators; Swietoslawski and
collaborators; Verkade and collaborators, and a few others.
Of
course, some of these investigators have themselves applied the
correction and record their result upon the basis of weight in vacuo.
Physical State. Unless otherwise specified (by <7 = gas, v = vapor,
s = solid), the values recorded refer to the combustion of the substance
in the liquid state, the final products of combustion being gaseous
carbon dioxide, liquid water, and nitrogen gas, for C, H, N compounds.
In the case of compounds containing other elements consult the discussion under the individual headings.
accuracy of the absolute value
is
desirable to bring the values to a
concerned.
common
basis,
V.
The
CALCULATION OF HEAT OF COMBUSTION
calculated values recorded in the tables refer to the heat of
combustion of the substance in the liquid state. Whenever, therefore,

the heat of combustion of a solid substance is recorded, it is necessary,
for the purpose of comparison, to convert that value to the liquid
basis. In making that conversion it is necessary, for precision work,
to know the molecular heat of fusion referred to 18 C. However, no
error of any magnitude is introduced into the calculation of the heat
of combustion of a liquid substance by merely subtracting the value
of the molecular heat of fusion at the melting point from the heat of
combustion in the solid state.
The general basis of calculating heats of combustion is discussed in
the paper of Kharasch and Sher. 14 Since the publication of this paper
a great deal of experimental work has been carried out by the writer
and various collaborators, which enables us to elucidate more fully
This will be done in papers which
the general formulas employed.
To conserve space, factors used will be diswill appear elsewhere.
cussed very briefly, and the user of the table is invited to consult the
original papers for the theoretical background and postulates.
It is assumed that, whenever an organic substance is burned in
oxygen, the heat generated is due to the interdisplacement of the
electrons between the carbon and oxygen atoms. It is assumed, also,
that the net amount of these energy interchanges in the form of heat
13
The
"
J.
corrected values given by Swietoslawski

Phys. Chem., 29, pp. 625 to 658; 1925.
(loc. cit.).
Kharasch)
equal to 26.05 kg-cali 5 per electron per mole,
is
if
365
the initial and final
stages correspond to the arrangement the electron occupies around
the carbon nucleus in methane and in carbon dioxide, respectively.

It is easy to perceive, therefore, that since the factor 26.05 corresponds only to certain definite initial and final stages of the electron,
whenever a substance is burned which contains some electrons displaced from that position the calculated value should be either smaller
or larger than the experimental value, depending upon whether the
electrons are nearer or farther from the carbon nucleus than those of
our reference position; that is, the arrangement of electrons around
the carbon nucelus in methane.
In the case of carbon compounds it is assumed that a sharing of
The lines merely indicate
electrons may exist, as represented below.
the distance which the electrons forming the bond may occupy with
respect to the two carbon nuclei A and B.
A
A 8 B
A
8 B
if
(1)
(2)
(3)
(4)
(5)
B
Fig.
Furthermore,
(1)
(6)
1.
denotes the arrangement of the pair of elec-
trons finking the carbon nuclei in ethane and the expression for the
heat of combustion of that compound is Q 26.05 X N, where

denotes the number of electrons, then it is self-evident that if (2),
(3), (4), (5), and (6) differ from ethane only in the arrangement of
one pair of electrons, then the expression for the heat of combustion
of these compounds should be:
Q=26.05XA^
(1)
Q=26.05XN+a
Q=26.05XN-b
(2)
(3)
Q^=26.05XiV c, where
(4)
than
c is larger
b.
Q = 26.05XN+d-e
Q = 26.05XiV+f
(5)
(6)
Bonds
of the type (5) and (6) need not be considered here, for (6) is
merely a special case of (2) and in (5) the two factors ordinarily
cancel one another.
The
four distinct types of bonds
tion of the following molecules:

1
ative
Bond
of type 1
compound.
may
be illustrated by a considera-
Aliphatic hydrocarbons, ethane as a represent-
366
of Research
Vol. 2
2. Bond of type 2.
A carbon-to-carbon linkage in which both
groups are weakly electronegative, such as a COOH next to COOH
next to COOH as in CH 3 .CO.COOH or two
as in oxalic acid or C =
triphenylmethyl nuclei (C 6 5 )3.C:C(C 6 5 )3.
3. A bond between a carbon of an aliphatic radical or any other

C-atom and a carbon atom of a strongly electronegative radical such
as phenyl; 15 thus,
4.
.CH3
bond between two carbon atoms

such as
H .C H
of
two strongly electronega-
naphthalene, anthracene, etc.

5
5
6
6
We have thus a general expression for the heat of combustion of
plus certain correction factors for
organic compounds, Q = 26.05
those electrons that are displaced from the reference position, the sign
of the correction factor indicating, except in the case of carbontive radicals,
XN
oxygen bonds, whether the electrons are displaced away from the
nucleus of the carbon atoms or toward the nucleus.
The correction factors, together with some illustrations, are

given below with the proper sign and should always be taken into
account whenever calculations are made. In the table only the type
formulas will be given. Thus, for example, the heat of combustion
of aromatic acids is given by the expression Q = 26.05 X iV 3.5, but
in calculating the heat of combustion of a substance such as o-toluic
acid, we have Q = 26.05X36- 3.5X2 -930.8, the 3.5 being the correction for the
VI.
bond
as in type 3,
and there are two such bonds.
STRUCTURAL CORRECTION FACTORS

For each
such
grouping
Sym-
Pair of electrons held
bol
between
add
or
subtract
as
indicated
Aromatic radical % Aliphatic radical

Examples
1. Mesitylene Q = 26.05X48-3X3. 5-= 1239.9.
2. Tertiary butylbenzene Q = 26.05X54 -3.5 1403.2.
Aromatic radical g Aromatic radical
Examples
1. Naphthalene = 26.05X48-6.5X2 = 1233.4.
2. Diphenyl
= 26.05X58-6.5=1497.9.
Ethylene bond C = C
Examples:
1. Trimethylethyiene Q = 26.05X30 + 13 = 794.5.
2.
Diamylene
(3
-3.5
6.5
+ 13.0
= 26.05X60+13 = 1576.0.
f
15
Kharasch and Marker, J. A. C. S., 48, p. 3130; 1926, for a table

organic radicals, and also Kharasch and Flenner (to be published).
Consult paper
negativity of
of
of relative electro-
zharasch]
VI.
367
STRUCTURAL CORRECTION FACTORS Continued

For each
such
grouping
add
Pair of electrons held between
or
subtract
as
indicated
Aromatic radical carbon
-6.5
Vinyl radical
Example Styrene Q = 26.05 X 40 + 13 - 6.5 = 1048.5.

Ethylene bond in ring system, as in cyclohexene
:
+ 6.5
Examples
1. Tetrahydrobenzene Q=26.05X34 + 6.5=892.2.
2. Methyl- 1-cyclohexene-l Q = 26.05X40 + 6.5 -=1048.5.
:
Acetylene bond
One
or
more replaceable hydrogens C=C
Example: Heptine-1 Q = 26.05X40 + 46. 1 = 1088.1.

No replaceable hydrogens
C=C R
Example Dimethyl diacetylene Q = 26.05 X 30 + 33. 1 X 2 = 847.7.
Aromatic radical carbon g Acetylene radical
+ 46.
+ 33.
scsc
-6.5
-.
Example: Phenyl ethine Q = 26.05X38 + 46.1-6.5 = 1029.5.

Alcohols
Aliphatic radical
Hydroxy 1 group (Primary
alcohol)
Example: Methyl alcohol Q = 26. 05X6 + 13 = 1 69. 3.

Secondary radical Hydroxyl group (Secondary alcohol)
Examples
1.
2.
Cyclohexanol Q = 26.05X34+ 6.5 = 892.7.

Amyl phenyl propargyl alcohol Q = 26.05X72 + 33. 1+6.5
-3.5 = 1911.7.
8 Hydroxyl group (Tertiary alcohol)
Examples
1. Methyl diethyl carbinol Q = 26.05X36 + 3.5 = 941.3.
Tertiary radical
2.
+ 13.0
+ 6.5
+ 3.5
Diphenyl phenyl ethinyl carbinol.
= 26.05X98 + 33.1 + 3.5-6.5-3. 5. 2 = 2576.0.
Aromatic radical
Hydroxyl group
+ 3.5
0" soh
.
Examples
1.
2.
Cresol Q = 26.05X34+3. 5-3.5 = 885.7.

Thymohydroquinol Q = 26.05 X 50 + 3.5 X 2 - 3.5 X 2 = 1302.5.
Acetal linkage
R.C
-(O-RO2
where R and Ri are aliphatic

Examples
radicals.
Q = 26.05X20+ 19.5X2 = 560.1.

Q = 26.05X40 + 19.5X2 = 1081.1.
1.
Glycol acetal
2.
Dipropyl methylal
+ 19.5
368
Bureau
VI.

Pair of electrons held between
Aromatic ethers.
Examples
1.
2.
m-Cresol methyl ether.

<H 26.05X40 + 19.5-3.5 = 1058.5.
Resorcinol dimethyl ether.
= 26.05X38 + 19.5X2= 1028.9.
R C=0
Aliphatic aldehydes
Example: Acetaldehyde Q = 26.05 X 10 + 13.0 = 273.5.
Aromatic aldehydes R.C =0

Example: p-Hydroxybenzaldehyde.
Q = 26.05X30 + 13.0-3.5 + 3.5 = 794.5.
O
Aliphatic ketones
R C R
Examples
1. Methyl propyl ketone.
= 26.05X28 + 6.5 = 735.6.
2.
Allylacetone
Q = 26.05 X 32 + 6.5 + 13.0 = 866. 1.
Aromatic ketones
O
o
r* xt
5
Example *Benzophenone Q = 26.05 X 60+ 6.5-3.5X2 = 1562.5.

If
R C =
radical
is
next to
COOH
R C
\h
radical
is
next to
OH
R C =
COOH,
as in
R-CIf
radical, as in
If
_C
OH
OH
is
next to CO, as in
rZ_.
O
s
-c^.r
For C = C bond
in cis compounds
in trans compounds
trimethylene ring in carboxylic acids, as in
For C = C bond
For
^
\OH
Example: Trimethylenecarboxylic acid.

Q = 26.05X 18 + 13 = 481.9.
vol. t
VI.
369
Eharasch]

For each
such
grouping
add
Pair of electrons held between-
or
subtract
as
indicated
For cyclobutane ring
_i
cH
+ 13.0
in carboxylic acids.
c-
\ OH
Example: Tetramethylenedicarboxylic
Q = 26.05X 24 + 13 = 638.2.
Acid anhydride
acid.
R.C-O-C-R
_.
Example: Succinic anhydride Q = 26.05 X 14+ 10 = 374.3.
+ 10.0
H H H
Lactone
HC-C-C-C=0
+ 13.0
H H
O
Example: Saccharic acid lactone.

Q = 26.05X 24+ 13 + 3.5 + 6.5 + 13.0 = 662.2.
+ 16.5
Esters (Aliphatic)
O
T>
"D
Example: Methyl acetate Q = 26.05 X 14 + 13 = 381.2.

Aliphatic radical
NH
+ 13.0
(Primary aliphatic amine)
Example: Propyl amine Q = 26.05X21 + 13 = 560.1.
Aliphatic radical
+ 19.5
Aliphatic radical
(Secondary aliphatic amine)
Example
Benzylethylamine
Aliphatic radical
Q = 26.05X49 + 19.5-3.4= 1292.5.

g
+26.0
(Aliphatic radical) 2
(Tertiary aliphatic amines)
Aromatic radical carbon
Aromatic radical
(Ammonia type
of nitrogen).
g N
-3.5
+ 6.5
(Primary aromatic amine)
Example: p-Toluidine Q = 26.05X37+6.5-3.5-3.5=963.3.
Aromatic radical
aromatic
+ 13.0
radical
(Secondary aromatic amine)
Example:
Diphenylamine Q = 26.05 X 59 + 13.0 - 3.5 X 2 = 1542.9.
Aromatic radical N (Aromatic radical) 2
Example:
TriphenvlamineQ = 26.05X87 + 19.5 -3.5X3 = 2275. 3.
For substituted amides, as in
H
R
= C and N
N CH
+ 19.5
+ 6.5
370
Bureau
VI.
[vol.

For each
such
grouping
Sym-
add
Pair of electrons held between-
bol
or
subtract
as
indicated
nn
PP
qq
For Nitrile radical aliphatic or aromatic,
+ 16.5
E,C=N
Example: Propionitrile = 26.05X17+16.5 = 459.3.

Aromatic radical carbon C=N
Example: Benzonitrile = 26.05X33 + 16.5-6.5 = 869.6.
For Carbylamine radical, aliphatic
-6.5
+ 33.
R-N=C
Example: Propyl carbylamine Q = 26.05X23 + 33. 1 = 632.2

rr
Aliphatic radical
+ 13.0
N.
%0
Example: Nitromethane Q = 26.05X6 + 13 = 169.3.
^0
Aromatic radical
N.
So
+ 13
Examples
1.
2.
Dinitrobenzene Q = 28.05X26 + 13X2 = 703.3.

Nitrotoluene Q = 26.05X34 +13 -3.5 = 895.2.
No equations are given for the fluorine, chlorine, and sulphur

compounds. However, an examination of the data reveals that the
general form of the equation Q = 26.05XiV+a holds fairly well, and
it is only necessary to evaluate "a" to obtain the equations for these
In the case of sulphur compounds it is also necessary
substances.
to use a factor different from 26.05 for the sulphur atoms which are
burned to S0 2 or S0 3
.
VII.
INDEX OF COMPOUNDS, BY CLASSES
The compounds recorded in the tables are classified in accordance

with the distinct types of organic molecules which they represent.
The calculation of the heats of combustion is thus facilitated. 16
1.
CH COMPOUNDS
Page
1.
2.
3.
4.
5.
6.
7.
8.
9.
16
Saturated hydrocarbons (aliphatic)

Poly methylenes
Aromatic hydrocarbons
Aromatic hydrocarbons (two or more aromatic nuclei linked together) _
Unsaturated compounds (aliphatic-ethylene)
Unsaturated hydrocarbons (aromatic)
Hydroaromatic hydrocarbons (unsaturated)
Terpenes
Acetylene hydrocarbons
A substance such
aliphatic acid.
as cinnamic acid would in this classification come under the heading

Other similar substances were classified in the same manner.
of
373
374
375
375
376
376
377
378
378
unsaturated
Kharasch]
2.
37
CHO COMPOUNDS
Page
10.
11.
12.
13.
Primary alcohols
Primary alcohols (cyclic)
Secondary alcohols
Hydroaromatic and polymethylene secondary alcohols
14. Tertiary alcohols
16.
Polyhydroxy aliphatic alcohols

Hydroaromatic and polymethylene glycols
17.
Phenols
15.
(all
types)
Aliphatic ethers
Aliphatic acetals
20. Aromatic ethers
21. Ethylene oxides (a-oxides)
22. Aliphatic aldehydes
18.
19.
23.
Aromatic aldehydes
24. Aliphatic ketones

25.
26.
27.
28.
Aromatic ketones
Quinones
Hydroaromatic and polymethylene ketones
Carbohydrates (monosaccharides)
29. Disaccharides
30. Trisaccharides, tetrasaccharides, polysaccharides
monobasic)
(hydroxy and keto acids)
31. Aliphatic acids (saturated

32. Aliphatic acids
33. Aliphatic acids (unsaturated)
34. Aliphatic acids (monobasic) (acetylene type)

35. Aliphatic acids (polybasic saturated)
36.
Hydroxy polybasic
acids (saturated)
37. Polybasic aliphatic acids (unsaturated)
Aromatic acids
Hydroxy aromatic acids
40. Phenylated aliphatic acids
41. Polybasic aromatic acids
42. Phenylated polybasic aliphatic acids
43. Hydroaromatic and polymethylene acids
44. Acid anhydrides
45. Lactones
46. Methyl esters of monobasic acids
47. Methyl esters of monobasic aromatic acids
38.
39.
48.
49.
50.
51.
52.
53.
Methyl
Methyl
esters of polybasic aliphatic acids
esters of polybasic aromatic acids

Ethyl esters of monobasic aliphatic acids
Ethyl esters of monobasic aromatic acids
Ethyl esters of polybasic aliphatic acids
Esters of aliphatic acids

aromatic acids
54. Esters of
55.
(all
(all
types)
types)
Phenol esters
56. Glycerol esters

3.
58. Aliphatic
59.
60.
6.1
N COMPOUNDS
amines (primary)
amines (secondary)
Aliphatic amines (tertiary)
Aromatic .amines (primary)
Aromatic amines (secondary)
57. Aliphatic
379
379
379
380
380
380
381
382
382
383
383
384
384
385
385
386
386
387
388
388
389
389
390
390
390
391
392
393
393
394
394
395
396
396
397
399
399
400
400
401
401
402
402
403
403
403
403
404
404
404
405
405
372
Bureau of Standards Journal of Research
ivoi.z
Page
62.
Aromatic amines
63.
64.
Amino
Amino
65.
Amides
66.
Acid amides (aromatic)
405
405
406
406
407
408
408
409
409
409
410
410
(tertiary)
acids (aliphatic)
acids (containing a phenyl radical)
(aliphatic)
67. Cyclic ureides, hydantoins, pyrimidines, purines

68.
69.
Ring nitrogen compounds

Ring nitrogen compounds, imides
70. Alkaloids (pyridine, piperidine, quinoline,
and isoquinoline)
71. Aliphatic nitriles

72.
73.
Aromatic nitriles
Carbylamines
74. Isocyanates (aliphatic)
75.
76.
77.
411
411
411
411
412
412
413
413
413
413
413
414
414
414
414
414
415
415
415
Hydroxylamine derivatives
Aliphatic nitro compounds
Aromatic nitro compounds
aromatic nitro compounds
Aromatic nitrophenols, phenetoles, nitranilines, nitroacetanilides
Aromatic nitroaldehydes
Aromatic nitro acids
Phenylhydrazones and osazones
Aldoximes (aliphatic)
Ketoximes (aliphatic)
Aromatic aldoximes and ketoximes
78. Substituted
79.
80.
81.
82.
83.
84.
85.
86. Nitrosamines
87. Nitramines
compounds
Azo compounds
88. Nitroso
89.
90. Substituted hydrazines

91.
92.
93.
Diazonium compounds
Azoxy compounds
Esters of nitric and nitrous acid
4.
94. Fluorine
(a)
(b)
.-
415
HALOGEN AND SULPHUR COMPOUNDS
compounds:
Fluoro-hydrocarbons (aliphatic)
Fluoro-hydrocarbons (aromatic)
Fluoro-alcohols
Fluoro-phenols
(e) Esters of fluoro-alcohols
(/) Ethers of fluoro-alcohols
(g) Ethers of fluoro-phenols
(h) Fluoro-acids (aliphatic)
(i) Fluoro-acids (aromatic)
(j) Esters of fluoro-acids (aliphatic)
(k) Esters of fluoro-acids (aromatic)
Fluoro-amides (aliphatic)
(Z)
(m) Fluoro-amides (aromatic)
(n) Fluoro-amines (aliphatic)
(o) Fluoro-nitramines (aliphatic)
(p) Fluoro-nitrobenzenes
(q) Fluoro-nitrotoluenes
(c)
(d)
(r)
(s)
(t)
(u)
Fluoro-anilines
Fluoro-anilides
F luoro-nitrophenols
Fluoro-nitranilines
_, ,-
.__-,
and nitrophenetoles
and nitroacetanilides
415
415
415
416
416
416
416
416
416
416
416
416
417
417
417
417
417
417
417
417
417
Kharasch]
95. Chlorine
(a)
(6)
(c)
373
compounds:
Page
418
418
418
419
419
419
419
419
420
Chlorinated hydrocarbons
Compounds
Compounds
H, O, and
C, H, 0, and
of C,
CI. (aliphatic)
of
CI. (aromatic)
Chloro-hydroquinols
(e) Chloro-quinones
(/) Chlorine compounds of C, H, N,
96. Alkyl bromides
97. Iodine compounds
98. Sulphur compounds
(d)
VIII.
1.
1.
TABLES OF DATA
CH COMPOUNDS
SATURATED HYDROCARBONS (ALIPHATIC)

Q=26.05XiV
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
Kg-cali5
(calcu-
lated to
J.)
(N)
CH4
CH-
Methane
C4H19C5H12-
Isobutane (g)
methane).
71-Pentane (g)
C 5 Hi
w-Pentane
C 3 H 8 __
2-
C5H12-
Hi2-
(g)
Ethane (g)
Propane (g)
Isopentane
Isopentane
(trimethyl
(g)
5
223; cf. 136.

223; cf. 136.
223.
838.3
3,511.6
833.6
170.
833.4
843.5
838.3
3,
491.
3, 533.
3, 511. 6
3, 523.
833.6
833.6
833.6
833.6
170.
170.
170.
223.
368.
526.
2,
72.10
72.10
72.10
72.10
72.10
Diisopropyl (v)
86.11
C7H16.
n-Heptane__
100. 13
1,
1,
842.
991.4
989.8
993.9
4, 149.
137. 3
149.
4,
C7H16C7H16C7H16C7H16-
2-Methyihexane
3-Methylhexane
2,2-Dimethylpentane
2, 3-Dimethylpentane
3,3-Dimethylpentane
C7H16.
C7H16C7H16-
2,4-Dimethylpentane
3-Ethylpentane
2,2,3-Trimethylbutane
100. 13
100. 13
1. 148.
100. 13
C 8 Hi 8 .
-Octane
114. 14
CsHig.
2,5-Dimethylhexane_
114. 14
147.
1, 302.
1, 304.
1, 305.
1, 303.
C 8 Hi8.
C H 18 _
C H 18 .
C Hi .
2-Methylheptane
3,4-Dimethylhexane
3-Ethylhexane
CsHig.
Hexamethylethane
114.
114.
114.
114.
114.
14
14
14
14
14
C10H22.
C10H22.
C16H34.
C20H42.
Decane
DiisoamyL..
Hexadecane (s)
142.
142.
226.
282.
18
1,
18
27
34
2,
8
8
8
2.2,4-Trimethylpentane
Eicosane
(s)
(s)
1,
2,
86.11
C 7 Hi 8 .
223;
364.7
521.0
677.3
210.
w-Hexane
. .
208.4
540.
201.
858.
CeHu.
CeHu.
(g)
881.6
16
Tetramethylmethane
4, 139.
5
756. 2
812. 3
4, 156.
4,
1,
146. 2
146.
146.
146.
146.
146.
100. 13
1,
1,
1,
148. 9
148. 9
4, 808.
100. 13
100. 13
4, 808.
1,
1,
148. 9
4,
1,
1,
148. 9
147.
808.
4, 808.
4, 804.
100. 13
100. 13
Literature
state)
30
44
58
C5H12.
the
liquid
1,
1.
9
149. 9
1,
1,
1,
1,
1,
1,
1,
306.
303.
302.
303.
301.
7
7
2
3
1,
4,
5,
7
3
5,
9
8
5,
610. 2
615. 8
559.
3, 183.
808.
4, 812.
4, 804.
5, 447.
5, 458.
5, 467.
5, 453.
1,
5,
5,
6,
6,
246.
246.
246.
215.
154.
163.
154.
1,
302. 5
1,
302.
302.
302.
302.
302.
1,
246.
246.
246.
246.
246.
1,
1,
2
5
9
5
464. 7
454. 7
448.
457.
448. 3
733.
757. 3
1,
1,
1,
1,
1,
1,
5
5
5
5
5
615.
615.
10, 709. 8
2, 552.
13, 321. 3
3, 178.
185.
215.
223.
114.
246.
2
2
2
2
2
146.
146.
146.
302.
1,
ef. 136,
37, 2, 65.
154.
154.
154.
246.
215.
153; cf. 244.
192.
192.
The above value is the average of 9 determinations which show a maximum variation of 1.1 per cent.
The variation between the highest and lowest result equals 1.1 per cent.
The variation between the highest and lowest result equals 0.9 per cent.
i The
variation between the highest and lowest result equals 0.4 per cent.
^
{
Note the large difference obtained by (170) for the two isomeric pentanes. This difference is rather
unusual, particularly in view of the fact that the 9 isomeric heptanes recorded in this report show almost
identical heats of combustion.
The heptanes used for this purpose at the Bureau of Standards were of
1
?
>3
a very high degree of purity. In view of that fact, no great reliance should be attached to the value for
isopentane until it is substantiated by other determinations.
6
Value uncertain, since tetramethymethane mixe4 with butylene was burned. The variation between
the highest and lowest result equals 0.2 per cent.
374
Bureau
[Vol.S
TABLES OF DATA Continued

1. CH COMPOUNDS Continued
VIII.
[2.
POLYMETHYLENES
Q=26.05X-tf 7
NumMolec-
Name
Formula
ular
weight
Kg-cahs
ber
Kg-calu
of
elec-
trons
(calcu-
Kilo-
(experi-
joules
mental)
(K.
lated to
J.)
(N)
CsHio
C5H10
C 6 Hi2
Trimethylene (g)
Methylcyclobutane
Cyclopentane
.
Methylcyclopentane
42
70.08
70.08
CoHi2
Cyclohexane
84.10
496.8
784.2
783.6
937.9
84. 10
10
Bicyclohexane
(0,1,3)
C Hu
C7H11
C7H14
C7H12
CsHib
Methylcyclohexane
Cycloheptane
Bicycloheptane
1 2,4-Trimethylcy clopentane
CsHie
CsHic
C Hi 6
C Hic
C H 18
8
8
9
3-D imethylcy clopentane
1-D imethylcy clohexane
1,3-Diniethylcyclohexane
1 ,4-D imethylcyclohexane
Methyley cloheptane
Methyl-1-n-propylcyclopen-
82.08
98.11
98.11
98.11
1,
9G. 10
112. 13
1,
13
13
13
13
126. 14
1,
112.
112.
112.
112.
1,
1,
1,
48
Literature
state)
the
liquid
1,
8 1,
1,
1,
2,
077. 6
3, 279.
915.
925.
933.
818.
6
9
6
8
8
3
3
4
561.
4, 565.
4, 547.
4, 308.
5, 208.
3
9
5,
936.
3,
937.2
3,
940.
912. 5
3,
090.
091.
087.
030.
245.
4,
242.
238.
228.
244.
401.
8
5
4
781.5
781.5
937.8
277.
3, 922. 3
3,
3,
937.8
cf. 37.
215.
165.
152.
91,
1,
1,
1,
7
3
223;
215.
215.
215.
094.
094.
094.
"l,~256.T
196.
5, 177. 3
5, 138. 8
5, 204. 5
1,
5,
860. 7
1,
1,
1,
1,
250.
250.
250.
250.
406.
4
4
4
4
215.
215; cf. 114.
114.
163.
215.
215.
215.
215.
215.
215.
tane.
C9H18
C 9 H,8
CgHig
1,3,4-Trimethylhexahydro-
CoHis
E thylcy cloheptane
CioHis
CioHis
CioHis
Fenchane
Thujane
Decahydronaphthalene
CioHis
Decahydronaphthalene
1,2,3-Trimethylcyclohexane
1,3,3-Trimethylcyclohexane.
126. 14
126. 14
126. 14
396.
394. 7
383.
5,
1,
5,
837. 7
832. 6
783. 7
1,
406. 7
406. 7
406. 7
215.
215.
144.
126. 14
1,
406.
5,
883. 2
1,
406. 7
215.
138. 14
1,
6,
284. 7
1,
510. 9
138. 14
1,
138. 14
1,
502. 8
506. 4
502. 5
6, 288.
1,
510. 9
1,
499. 5
6,
1,
510. 9
1,497.4
215.
175.
169; cf. 173,
82.
105.
173; cf. 82.
1,
510. 9
215.
1,
563.
215.
2, 136.
215.
1,
8
1,
5,
1,
1,
benzene.
6,310.3-
(cis).
138. 14
(trans).
275. 4
Methyl-l-tt-propyl-3-cyclohexane.
10 (1-Isopropyl4-rnethylcyclohexane)
140. 16
1,
502. 9
6, 285.
C10H20
p-Menthane
140. 16
1,
514. 6
6,
C 14 H26
3,3-Dimethyldicyelohexyl
194. 21
2, 105.
C10H20
334.
8, 806. 9
m-Hexahj droditolyl)
for trimethylene and its derivatives and bicyclo compounds containing trimethylene rings.
Swietoslawski (J. Am. Ch. Soc, 42, p. 1315), 1920, believes that the heats of combustion of these comare in error and recommends that they be redetermined.
8 This value is probably in error.
The work of this investigator does not agree well with the values of
modern workers.
w The author (215) calls the compound "Caromenthane." The heat of combustion of this compound
would certainly bear reinvestigation.
Except
pounds
Kharasch]
VIII.
1.
375

CH COMPOUNDS Continued
3.
AROMATIC HYDROCARBONS
Q=26.05XiV-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
Kg-cali5
ber
(experi-
Kilojoules
mental)
(K.
Kg-calis
of
elec-
trons
(calcu-
J.)
C 6H
6-
Benzene
Benzene
C7H8..
Toluene
CgHio.
787.2
783.4
782.3
937.0
934.2
78.05
(v)
78.05
92.06
o-Xylene
1,
106. 08
1,
1,
ra-Xylene
106. 08
C Hio.
C 8 Hio.
p-Xylene
Ethylbenzene
106. 08
1,
106. 08
1,
C9H12C9H12C9H12C9H12-
Mesitylene
w-Pr opyl benzene
Isopropylbenzene
120. 10
120. 10
1,
Hio.
Literature
state)
(iV)
CeHo-
lated to
the
liquid
1,
094.
091.
091.
088.
3,
3,
3,
3,
3,
294. 4
277. 7
277.
920.
913. 4
4, 578.
7
7
4,
4,
559. 3
4,
089.
091.
781.5
934.3
165; cf. 203,

153.
1,
087.
1,
087.
556. 8
6
1,
087.
087.
1,
9
7
1,
1,
859. 3
832. 2
1,
154.
152.
152.
165; cf. 154,
203.
154; cf. 152,
152; cf. 138.
567. 7
4, 567.
4, 565.
200.
153.
165; cf. 15*.
152.
1,
4.11
1,
243.
246.
247.
241.
203.
5, 214.
5, 218.
5, 195.
5,
(1,2,4-Tri-
120. 10
120..10
feri-Butylbenzene
134. 11
1,
134. 11
1,
400. 4
393. 6
5,
1,2,4, 5-Tetramethylbenzene
C10H14
(Durene).
iso-Propyltoluene
134. 11
1,
412.
5,
n-Propyltoluene
(1,3)
134. 11
1,402.8
405. 4
5,
C10H14
12 1,
CioHu
CiiHw
Isopropyltoluene
(1,3)
134. 11
148. 13
12 1,
Pseudocumene
1,
48
1,
1,
239.
246.
246.
239.
9
9
9
152; cf. 203.

152; cf. 73.
152; cf. 73.
152.
methylbenzene)
CioHm
CioHm
1,
403. 2
392. 7
910. 5
866. 5
878. 8
1,
399. 7
73.
895.
503.
164.
926.
577.
1,
73.
5
3
1,
1,
399.
545.
700.
660.
816.
946.
957.
996.
12, 974.
9
4
9
2
5,
152; cf.
188.
(s)
(1,4)
(Cy-
mene)
C12H18
C13H12
C14H14
Pentamethylbenzene (s)
Hexamethylbenzene (s)
Diphenylmethane (s)
Dibenzyl (s)
C19H15
Tripbenylmethyl
C19H18
Triphenylmetbane
162. 14
168. 10
"
(s)
(s)
409. 5
554.
6,
1,711.9
7,
655.
810. 6
6,
1,
182. 11
64
70
243. 12
91
244.13
92
1,
1,
2,
2,
3
7
4
378.
379.
388.
3, 102.
2,
C25H20
Tetr aphenylmethane
320. 16
(s)
120
5,
5,
7,
9,
9,
9,
182.
203.
1,
1,
2
5
2,
373. 5
386.
3,
112.
2,
182; cf. 179.

182.
179.
182.
179.
179.
n The authors (4) report the heats of combustion of two samples of ethylbenzene prepared by the Fittig
and Clemensen methods, respectively. The calorimetrie determinations were carried out by Langbein
and agree within 0.1 per cent with the value recorded by (152). Of interest is the fact that, while the two
samples have almost identical heats of combustion within 0.2 per cent, the sample obtained by the Clemensen method has the higher density and index of refraction.
12 The values of this investigator are about 0.4 per cent
too high as compared with those of Richards and
Barry (16).
1 3 The author
(179) gives, also, the heat of combustion of tripbenylmethyl peroxide and the heat of combustion of the addition product of hexaphenylethane and ethyl acetate.
" This molecule contains one displaced electron; hence the formula for it becomes 26.05X^+13=2,373.5.
AROMATIC HYDROCARBONS
4.
(Two
or
more aromatic
nuclei linked together)
Q=26.05X-ZV-3.5a-6.5b
1,
CioHg.
Naphthalene
128. 06
(s).
48
1,
1,
C12H10
Ci 2 10
Diphenyl (s)
Acenaphthene
(s),
(peri-
154. 08
154. 08
1,
1,
232. 5
231. 8
229. 9
5,
158.
150. 2
147.
1,
233. 4
5,
493. 6
491. 3
6,
250. 7
1,
497. 9
491.
5,
6, 241.
1,
80.
52.
221; cf. 188,
241, 232,
63.
188; cf.47.i5
182.
ethylenenaphthylene)
15
These authors give the heats of combustion of a freshly prepared sample of diphenyl and one 20 years
being 11.2 kg-cahs per mole. The authors accept the higher value of 1,510.1 kg-cali5 for
the fresh sample as the correct value and believe that the new sample is of a higher degree of purity than
the old sample.
old, the difference
3697
29
376
Bureau
TABLES
VIII.
"OF
[Vol.
DATA Continued
1.
AEOMATIC HYDROCARBONS Continued
4.
(Two
or
more aromatic nuclei linked together)

Q=26.05XiV-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
of
elec-
trons
(calcu-
Eg-cali5
Kilo-
(experi-
joules
mental)
(K.
lated to
J.)
Literature
the
liquid
state)
C13H10
Fluorene
ChHio
Anthracene
ChHjo
Phenanthrene
(s).
166.
08
G2
178.
08
66
178.
08
66
228. 10
234. 14
306. 14
356. 16
584.
6,
1,693.4
1,700.4
1,691.6
7,
1,
692. 5
84
90
2,
139.
306. 8
9, 653.
114
2,
1,
(
(s)
\
I
(s)
Ci 8 Hi2-
Retene (s) (Methylisopropylphenanthrene)

C24H18C26H20
1,3,5-Triphenylbenzene (s).
Dianthracene
(s)
5.
2,
3,
1,
7,
628.
086.
116. 2
079. 3
083.
8,
952.
2, 159.
7,
7,
936. 7
382. 9
12, 290.
1,
595. 1
705. 3
163.
188.
240
1,
217.
188.
693. 3
2,
311. 5
2,
940. 2
182.
182.
182
14, 147. 3
240.
UNSATURATED COMPOUNDS
(Aliphatic-ethylene)
Q=26.05XiVr+13
C2H4-.
Ethylene
C3H6C H 8-
Propylene (g)
Isobutylene (g)
28
(g)
Amylene
C5H10-
C
C
C
fTrirnethylethylene (v)
Hi2.
10 -
- _
\Trimethylethylene liquid
Hexylene
Diallyl (v)__._
Hio.
42
56
70
70
70.08
84.10
82
24
30
30 /
803.
796.
36
34
952.6
/
I
Diisobutylene
CsHie.
C10H20
C12H24
i6
I?
is
17
112. 13
140. 16
168. 19
Diamylene
Triisobutylene
Thomsen's value
is
18
345.
331. 6
490.2
647.2
803.4
18
48
60
72
1,
1,
1,
928.
903.
252. 4
582. 2
858. 3
probably more reliable than the higher value
(CH CH.CH:CH.CH.(CH 2
(CH )2.CH.C[CH2.CH.(CH )2]: CH.CH (CH
3) 2
3)
6.
of
1,
8
5
387.
051.
2, 708.
3, 362.
3, 363.
3, 328.
3, 983.
3, 884.
3, 778.
5, 237.
6, 616.
7, 771.
136.
223.
223; cf. 37.
481.9
638.2
794.5
5
2
223
794. 5
9
8
..
950.8
911.7
1,
263. 4
576.
888. 6
1,
048. 5
1,
8
4
1,
65; 'cf. 98.

223.
215.
215.
223.
38.
128.
6.5.
128.
Mixter.
325.6
1,444.5
2,
3) 2 .
UNSATURATED HYDROCARBONS
(Aromatic)
Q=26.05XiVr+13-6.5d
Styrene (Phenylethylene)...
104. 06
40
1,
1,
045. 4
047.
4,
4,
375.
386. 3
182.
7;
cf.
138,
104.1. 20 .
a-Methylstyrene._
C9H10CbHio-
/8-Methylstyrene
C10H12C10H12-
(8-Dimethylstyrene
0-Ethylstyrene
118. 08
Q?-Tolyl-
1,
118.08
46
46
132. 10
132. 10
52
52
1,
1,
202. 9
202. 4
038. 9
5, 036. 9
1,
357. 2
346.
5,
685.
638. 8
1,
5,
204. 8
1, 204.
7;
361.
361.
7.
ethylene).
a,
(s)
1,
5,
1,
cf. 104.
163; cf.
104.
7,
6; cf. 7.
and substitution products of that compound which are about

1.4 per cent higher than the values given by (7).
As the details of the former (8) work are entirely lacking,
and since, in general, the work of (7) is most painstaking, we may safely assume that the values of (104) are
in error, and that his results are at least 0.8 per cent too high.
No greater accuracy than 0.3 to 0.5 per cent
19
The author
(104) gives values for styrene
can even then be attached to his values.

20 Recently Swietoslawski and Popov
(J. chim. phys., 22, p. 397; 1925) have attempted to correct Lemoult's values by introducing a correction of 0.5 per cent. While it is possible that the result of this
investigator contains a systematic error, yet we do not believe that this correction brings all of Lemoult's
values into agreement with those of later investigators, which indicates other sources of error. In the
tables the corrected values are recorded.
377
Kharasch]

1. CH COMPOUNDS Continued
VIII.
6.
UNSATURATED HYDROCARBONS Continued

(Aromatic)
Q=26.05XiV-fl3-6.5d
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
of
elec-
trons
(calcu-
Kg-calis
Kilo-
(experi-
joules
mental)
(K.
lated to
the
liquid
J.)
Literature
state)
Phenyl-l-butene-2
C10H12
C10H12
132. 10
132. 10
CiiHh-
146. 11
160. 13
C12H16C14H12 _
C14H12C15H14
CieHi4
Stilbene (s) (symm. Diphenylethylene)
180. 10
/3-Methylphenylstyrene (s).
Diphenylbutadiene (s) (la-
a,
.
180. 10
194. 11
206. 11
52
52
58
64
68
1,
1,
1,
1,
1,
68
1,
74
78
1,
2,
361. 2
356. 9
510.
664. 9
765.
702.
675.
325.
6, 974.
7, 381.
770.
937.
056. 9
8, 608.
2, 044.
2,
5,
5,
6,
1,
9
4
3
2
405. 9
7,
8, 106.
1,
1,
1,
1,
1,
1,
364.
364.
517. 4
673. 7
771.
771.
927. 7
7.
138.
6.
6; cf. 7.
183; cf. 163,

144, 9.
9.
104.
172.
bile).
CieHu
Diphenylbutadiene
(cis-
206. 11
78
2,
035.
8, 516.
Ci 6 Hi4
Diphenylbutadiene (s) (trans-
206. 11
78
2,
030. 3
8,
232. 13
234. 14
88
90
2, 2S7.
2,
7
342. 2
9, 574.
9,
Dibenzylbutadiene (s)
4-ethyl-l-buDiphenyl-1,
234. 14
90
92
2,
341.
372. 6
9, 797.
2^236. 15
256. 13
96
(s)
044. 9
172.
cis).
trans)
172.22
2, 031.
Diphenylhexatriene (s) 23
6-Diphenylhexadiene-l,
C18H16
496. 8
1,
2,
811. 5
2,
318. 4
355. 5
172.
163.
(s).
2,
2, 357.
172.
939. 3
2,
399.
7.
10, 493. 5
2,
494. 3
104.
9,
tene-3.
C2Hl6
21
This value
is
about
per cent too high.
"2,508.6
would be
better value
See footnotes 19 and 20'
1,929.2
p. 376.
22
23
2*
25
For trans isomers the correction is 6.5 for the double bond.
The purity of this product is rather questionable.
CeHs.CH (CH .CH ).CH2.CH = CH.C6H 6

The values of this investigator for this series
2
would be
Consult p.
368.
are uniformly too high
by
0.5 per cent
better value
2,496.1 kg-cahs.
7.
HYDROAROMATIC HYDROCARBONS
23
(Unsaturated)
(2=26.05X^+6.56
Dihydrobenzene
80.06
32
CfiHio.
D m e t h y lmethylenecyclo-
82.08
34
C 8 Hio-
Tetrahydrobenzene
82.08
34
8 _.
484. 4
548.
833.
847.
3,
898.0
3, 755.
891.
893.
891.
3, 727.
3,
846.6
215.
197.
215.
892.2
215.
165.
197; cf. 91."
propane.
(cyelo-
hexene).
C7H12-
Methyl-l-cyclohexene-3
96.10
40
C7H12-
Methyl-1-cy clohexene-1
96.10
40
C7H12-
Methylenecyclohexane
96.10
40
Cycloheptene
C 8 Hi2.
1 , Methyl-3-methylenecyclo-
96.10
108. 10
743. 7
732. 6
1,
4, 353.
1,
048. 5
048. 5
1,
055.
215.
163.
91.
1,
1,
048.
4, 390.
1,
4
3
40
44
215
4, 364. 3
C7H12-
043. 6
1,040.9
1,
f
3,
3,
215.
165; cf. 162.
044.
4, 366.
1,051.4
1,054.9
4, 404.
049. 9
149. 2
4, 390.
1,
4, 814.
1,
048. 5
16S. 7
215.
162.
1,
4,
414. 8
hexene-1.
12
1,3-Dimethyldihydroben-
1,4-Dimethylcyclohexadi-
28
108. 10
44
1,
148. 2
4, 801.
1,
159.
215.
108. 10
44
1,
152. 2
4,
826. 6
1,
159.
165.
110. 11
46
1,
203. 7
5,
042. 3
1,
204.
165; cf. 162.
zene.
C Hi
8
ene-1,3.
Hi4.
E thyl-1-cy clohexene-1
In the case of 1,4 conjugated systems, the correction factor for each double bond should be not 13, but
a smaller value, say 6.5, in agreement with the lower reactivity of these compounds. It is, however, omitted
here, for the data at hand do not allow one to draw far-reaching conclusions and are too conflicting.
27
This author gives the heat of combustion of cyclohexene as 898.8 kg.-cahs Whether it is for constant
volume or constant pressure he does not state, and he gives no experimental details of any kind except that
he used the internationally accepted value for benzoic acid.
23 Compare values obtained by (215) and
(197) for dihydrobenzene.
26
378
of Research
[VokS

VIII.
1.
7.
HYDROAROMATIC HYDROCARBONS Continued

(Unsaturated)
Q=26.05XiV+6.56
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
of
elec-
trons
(calcu-
Kilo-
Kg-calis
(experi-
joules
mental)
(K.
lated to
J.)
the
liquid
state)
CsHh.
C 8 Hu_
E thylenecyclohexane
C 8Hi4-
(1,1,2-Tri?so-Laurolene
methylcyclopentene-2)
1 ,3-D imethylcyclohexene-3_
l-Methyl-4-ethylcyclohexa-
Hi4.
C9H14-
Laurolene
059.
987. 9
1,
1,
211. 3
204.
1,
204. 8
1,
5,
4
490. 9
1,
204. 8
315. 5
5,
611. 2
1,
361.
2
9
6
6
7
1,
302.
1,
302.
347. 6
110. 11
110. 11
1,
1,
207. 7
192. 7
4,
110. 11
1,
193.
4, 990.
110. 11
122. 11
1,
4, 995.
1,
194. 5
310. 8
124.13
1,
340.
1,
296.
312.
298.
339.
352.
5,
diene-1,3.
16 .
Isopropyl-l-cyclohexene-1.
C 10 Hio.
Ai-Dihydronaphthalene
130.
C10H10-
Aa-Dihydronaphthalene (s) _.
130. 08
C10H12.
Tetrahydronaphthalene
132. 10
08
1,
1,
1,
1,
CioHhCioHieCioHigCioHie-
Hexahydronaphthalene
Octohy dronaphthalene
Isobutenyl-l-cyclohexene-1l,5-dimethyl-3-vinylcyclohexene-1.
C10H16-
l-Methyl-4-isopropylcyclo-
C 10 Hi8-
l-Ethyl-5-dimethylcyclo-
C10H18CiiHis-
Menthene
6
4
429.
5, 488.
5, 438.
5, 611.
5, 655.
3
7
935. 5
1,
6,114.3
1,
3
5
3
5,
11
13
13
13
1,
1,
419.
461.
461.
455.
136. 13
1,
470.
6, 160.
138. 14
1,
504. 5
6,
138. 14
1,
150. 14
1,
523. 2
615.
134.
136.
138.
136.
1,
1,
8
7
1,
6, 123. 5
6, 097.
1,
1,
419.
465.
478.
478.
1,
471.
5,
7
3
3
3
hexadiene-1,3.
302. 4
1,517.4
374.6
765.2
1,
094.
162.
1,
hexene-1.
(
3 -Terpene)
l,5-Dimethyl-3-isopropene-
1,
517.
634.
cyclohexene-i.
8.
TERPENES
3=26.05X^+130+6.56
CioHieCioHieCioHieCioHie-
Z-Limonene
d-Limonene
136. 13
136. 13
<Z-"Citrene"
136. 13
d-a-Pinene (Australene)
CioHis-
Z-a-Pinene (Terebcnthene)..
C10H16CioHie-
/3-Pinolene
6,
1,
457. 2
471. 2
473.
471. 9
1,
473. 2
6, 160.
1,480.5
6, 195.
6, 135.
1,
469. 3
464. 7
467. 6
1,468.8
6, 144.
1,
136. 13
56
56
56
56
136. 13
56 /
136. 13
136. 13
56
56
1,
1,
Sylvestrene
C10H16-
Camphene(s) cryst
136. 13
56
CioHisCioHieCioHie-
Terecamphene (inact.)..
Borneocamphene
136. 13
136. 13
Cyclene(s) (Tricyclene).
CioH 16 -
a-Terpinene
136. 13
136. 13
56
56
56
56
).
1,
1,
1,
1,
1,
1,
466.
470.
467.
470.
6,
5
155. 5
1,
477. 5
477. 5
1,
465. 3
6, 164.
6,
6,
6,
154.
147.
7
2
6, 138.
6, 146.
6,
9
9
9
6
8
1,465.3
1,
1,
1,
471. 8
471.
1,
471.
1,
8
5
159. 5
6, 152.
477. 5
471.
ACETYLENE HYDROCARBONS
Q=26.05X i^+33.1h+46.1g
C2H2C3H4CeHe-
Allylene
(g)
(g)
(Ethine)
(Propine).
9 -.
26.02
10
40
16 /
78
30
29
Dipropargyl
(v)
(1,5-Hexa-
diine)
C7H12-
Acetylene
Dimethyldiacetylene
(2,4Hexadiine)
Heptine-1
(PhenylPhenylacetylene
78.05
30
96.10
40
38
1,
102. 05
130. 08
202. 08
50
74
1,
1,
312.
1,
304.
465.
473.
853.
882.
1,
945.
978.
570.
694.
546.
1,
3,
3,
847.8
3,
091. 2
024. 2
4,
306.1
462.9
5
6
2
9
873.7
847. 7
4,
564. 5
284. 2
1,
5,
605. 2
1,
1,
1,
088.
029. 5
ethine).
C10H10CieHio29
The author
Phenyl- l-butine-3
Diphenyldiacetylene
(137) gives also
(s)
1,
the heat of explosion of acetylene.
340.
975. 6
8, 267.
342.
980. 9
379
EMrasch]
VIIL

2. CHO COMPOUNDS
10.
PRIMARY ALCOHOLS
Q=26.05XiV+13
NumMolec-
Name
Formula
ular
weight
CH
Methyl
0._
alcohol
C 2 H 6 0_
Ethyl alcohol.
C3H4O.
Propargyl alcohol
C
C
3
3
32.03
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
Kg-calis
(calculated to
J.)
170.9
6
/
327.
329.
1,
714.7
169.3
370.
378. 5
325.6
12
56.00
14
428.9
1,
793. 7
423. 8
Allyl alcohol
58.05
16
442.4
1,
w-Propyl alcohol
60.06
18
442.8
481.7
850.
022.
009.
674.
678.
668.
293.
310.
320.
(v)
/
1
f
1,
483.
480.
638.
640.
2,
2,
2,
4
4
C4H10O.
m-Butyl alcohol
74.08
24
C4H10O.
C 6 Hi 2 0.
Isobutyl alcohol (primary)
74.08
88
24
30
638.2
787.3
2,
88.10
30 /
791.
793.
3,
1,
104. 9
4, 620.
3,
727. 9
742. 7
1,
891.
894.
262.
5,
278. 9
C 6 Hi
Amyl
Amyl
0.
alcohol
(?)
alcohol (ferm.)
30
n-Heptyl alcohol
116. 13
42
Benzyl alcohol
108. 06
34
CsHisO.
Octyl alcohol
CgHuO.
C 9 H 0..
Amylpropargyl alcohol
C 7 H 16 0.
C H 0_
Phenylpropargyl alcohol
Hexylpropargyl alcohol
Cetyl alcohol (s)
CgHieO.
CigHsiO
30
31
Mostly isobutyl
carbinol.
_.
32
130. 14
48
126.11
132. 06
44
42
50
96
140. 13
242. 27
1,
1,
1,
2,
PRIMARY ALCOHOLS
11.
2,
3,
3,
3,
191.
137. 3
340.
504. 5
984.
4, 757.
5, 605.
10, 481.
4,
C5H11.CSC-CH2OH.
31
Literature
state)
46.05
H 0.
H 0.
the
liquid
32
(Cylic)
8
9
3
638.2
1,
107.
895. 2
1,
263. 4
1, 192.
33
133. 7
348. 6
513.
8
2,
6
3
Cells.
111.
153.
215; cf. 110.
215.
229; cf. 153.
153; cf. 215.
65.
~794.~5~
153; cf. 172,

191, 223.
153.
172; cf. 3,
64.
223.
1,
1,
215.
110.
215.
179.
182; cf. 205.
115.
138.
138.
138.
181.
CSC-CH2OH.
33
Q =26.05X-ZV+13
C6H10O
C7H140
33
Among
thelot
Cyclobutyl carbinol
Cyclohexyl carbinol
86.08
.
114. 11
28
40
1,
747. 8
047. 2
3, 127.
4, 379.
3
4
742.4
1,
055.
215.
215.
the cyclic alcohols should be included cholesterol. However, it is omitted here because Ber17, p. 433; 1899,who determined the heat of combustion of cholesterol,
compound C26H44O. The present accepted formula is C27H46O.
and Andre, Ann. chim. phys., (7)
give for the formula of the
12.
SECONDARY ALCOHOLS
Q=26.05XiV-r-6.5
C3H3O..
C5H10O.
CHuO_
Isopropyl alcohol
Ethyl vinyl carbinol..
Pinacolyl alcohol
C7H12O.
C 13 Hi 2
Diallyl carbinol
Diphenyl carbinol
C14H13O
Amylphenylpropargyl
C5H10O2
C 6 Hi 2 0.
60.06
86.08
474.8
752.9
938.6
102. 11
112. 10
18
28
36
38
1,
184. 10
62
1,
alco
202. 14
72
1,
Dimethylolcyclopropane.-/3 Methyl cyclopentanol
102. 08
100. 10
Cyclohexanol
l,3-Dimethylcyclopentanol-2
100. 10
114. 11
34
40
1,
030. 5
Ethyl-l-cyclopentanol-2
/3-Methyl cyclohexanol
Cycloheptanol
l-3-Dimethylcyclohexanol-2_.
114. 11
114. 11
40
40
40
46
1,
46
52
56
56
1,
(s).
475.4
748.9
944.3
1,022*4
028. 2
615. 4
985. 6
6
925. 2
4, 299. 9
6, 760. 5
1,
614. 6
215;
111.
215.
215.
182;
901.
7,
910. 4
1,
921. 7
138.
707.6
887.6
890.7
2,
959. 2
892.7
892.7
1,
3, 148.
3,
cf.
110.
cf.
179.
hoi. 3 *
CeHwO.
C7H14O.
C7H14O.
C7H14O.
CtHhO.
C Hi 0.
8
CsHieO.
C 9 Hi 8 0.
CioHisO
CioHi 8
CioHisO
C,oHi 8
114. 11
128.13
3-Dimethylcyclohexanol-5
Cycloheptylmethyl carbinol _
Thujyl alcohol
Borneol (Borneo camphor) _.
128. 13
142. 14
Borneol (synthetic)
154. 14
154. 14
CioHwO
rf-Borneol
l-B orneol
C10H20O
Menthol
(s)
(s)
154. 14
154. 14
1,
1,
1,
1,
1,
35
1,
1,
154. 14
56
56
56
156. 16
58
1,
m C 8 HuC=0-CH(OH)(0H).
1,
1,
724. 9
4, 309. 6
1,
048. 5
215.
215.
153; cf. 215.
215.
039.
038. 4
050. 2
196.
4, 345.
1,
048.
048.
048.
204.
215.
215.
215.
215.
183. 4
342. 2
4,
3,711.9
3,
4,
1,
1,
001. 7
1,
949.
5, 613.
6, 189. 3
6, 145. 9
1,
6, 136.
131. 9
6, 134. 4
6, 309. 8
1,
5,
477. 5
469. 6
466.
466.
467.
508.
342. 6
4, 391.
2
6
2
8
6,
35
Mean
5
5
1,
204. 8
361.
1,
465. 3
1,
465.
465.
485.
517.
1,
1,
value.
3
3
215.
215.
175.
125.
183; cf. 125
89.
89.
113.
380
Bureau
VIII.
2.
13.
TABLES OF DATAContinued
CHO COMPOUNDSContinued
HYDROAROMATIC AND POLYMETHYLENE SECONDARY ALCOHOLS

Q=26.05XiV+6.5
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
Kg-cahs
of
elec-
trons
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
the
liquid
J.)
Literature
state)
C Hi
8
05
Quercitol
CeHiaOe
Inositol
164. 10
180. 10
(s)
(Inosite).
(s)
704.2
662.1
26
24
2,
195
947.
2, 770.
195.
TERTIARY ALCOHOLS
14.
Q=26.05XiV+3.5
C4H10O.
Trimethyl
74.08
24
629.3
2,631.7
628.7
215;
C5H12O.
butyl alcohol).
Dimethylethyl carbinol
88.10
30
784.6
C0H12O.
Allyldimethyl carbinol
100.10
34
785.0
902.2
CeHnO.
Methyldiethyl carbinol
102. 11
36
281. 2
707. 3
821.
876. 7
215; cf. 110.

215.
113.
215.
C7H14O.
C7H16O.
C HhO.
C Hi 0.
Allylmethylethyl carbinol...
Triethyl carbinol
Diallylmethyl carbinol
Allylrnethylpropyl carbinol-.
CsHisO.
Allyldiethyl carbinol
114.
116.
126.
128.
128.
11
13
11
13
13
40
42
44
46
46
CsHisO.
C9H13O-
Methyldipropyl carbinol...
Allylmethyl-n-butyl
car-
130. 14
142. 14
48
52
142. 14
52
54
1,
carbinol
Text.
/
\
1,
1,
1,
1,
1,
3,
886.
913.
3,
927.0
3,
050.
080.
180. 7
201. 9
207.
4, 391.
1,
4,
1,
3,
4,
5,
5,
941.3
5
516. 6
937. 7
1,
026. 4
048.
1,
1,
1,
8
8
215.
215.
215; cf. 113.
215.
215.
1,
371.
215.
1,
410. 2
215.
488. 3
527. 4
215.
215.
113.
215.
182; cf. 179.
1,
363.
5,
700.
1,
386. 5
5,
798.
472.
6, 156.
3
348. 3
1,
5, 708.
215.
215.
5, 155.
1,
115.
253. 9
371.
232. 7
364. 9
1,
058.
097.
175.
214.
214.
cf.
1,
binol.
CoHigO.
Allylmethyl-ieri.-butyl car-
C9H20O.
Ethyldipropyl carbinol
CieHisO-
Diallylpropyl carbinol
154. 14
56
binol.
C10H20O.
Allyldipropyl carbinol
156. 16
58
C11H22OCi 9 Hi0_
C21H16O.
Allylmethylhexyl carbinol- ..
Triphenyl carbinol (s)
Diphenylphenylethinyl car-
170. 18
260. 13
284. 12
64
C7H14OC 8 Hi 6 0CsHieO.
CoHieO-
l,3-Dimethylcyclopentanol-3
l,2-DimethylcyclohexanoI-2_
l,3-Dimethylcyclohexanol-3.
1,3, 5-Trimethylcyclohexene-
90
98
/ 1,518.0
\ 1,549.6
1, 666. 7
2, 340. 8
2, 572. 3
6,
1,
480. 4
970.
9, 796. 3
10, 757.
6,
6,
683. 7
337. 5
576.
95.
1,
045. 7
201. 8
201.
312. 5
215.
163.
215.
215.
1,
358.
215.
1,
468.
125.
1,
2,
2,
binol. 36
114. 11
128. 13
128. 13
140. 13
40
46
46
50
4, 324.
1,
034.
196. 5
192. 5
294. 7
52
1,
322.
5, 530.
58
1,469.5
up to
1,480.0
1,
1,
1,
1,
012.
1,
4, 987.
1,
5,
5,
414. 4
8-01-5.
l-Methyl-3-ethylcyclohexan-
CgHisO.
ol-3.
f
Terpineol (s)._
CioHisO..
154. 14
{
{
Terpine hydrate
C10H22O3.
(C 6 H 5 ) 2
36
:-C-C=C-CoH
190. 18
(s)
1,
451.
6, 145.
6, 189.
125.
6, 068.
OH
15.
POLYHYDROXY ALIPHATIC ALCOHOLS

Q=26.05XiV+13j+6.5k+3.51
C2H6O2C3H8O2C3H8O2-
3-
Ethylene glycol
37
__
Propylene glycol-..
Isopropylene glycol.
Glycerol
C4H10O4-
Erythritol
C5H12O4C5H12O5C6H14O2-
Pentaerythritol (s)
...
Arabitol (s)
Pinacol (s) (Tetramethylethylene glycol).
(s).
286.5
436.3
442.8
397.2
195; cf. 109.

111.
111.
1,
179.
802. 4
823. 8
661. 5
2,
109. 7
507.9
182; cf. 126,
767.
2, 560. 4
3, 753. 8
657.7
618.6
898.7
195.
195.
115.
62.05
76.06
76.06
92.06
10
16
16
14
281.9
431.0
436.1
397.0
08
18
504.1
136. 10
152. 10
118. 11
24
22
34
661.2
611.8
897.6
2,
122.
1,
1,
1,
195; cf. 181,

64.
31.
37
The heat
Wm.
of combustion
H. Rinkenbach (156) as
are given,
of diethj^lene glycol,
566.7 kg.-cahs per mole.
HO-CH2.CH2.O-CH2.CH2OH (liq.), is given by

No experimental details as to procedure employed,
Kharasch]
VIII.
2.
15.
381

CHO COMPOUNDSContinued
POLYHYDROXY ALIPHATIC ALCOHOLS Continued

Q=26.05XA7+13j+6.5k+3.51
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
trons
(calcu-
Kilo-
Kg-calis
of
elec-
(experi-
joules
mental)
(K.
lated to
the
J.)
(N)
CeHuOe
CeHuOe
Dulcitol
CtHkjOt
Perseitol
C8H14O2
(d-mannoheptol)
Tetramethylbutinediol
C Hi
Tetramethylbutenediol
02
(Glucoheptol)
state)
727.6
729.1
3,
723.
3,
182. 11
26
182. 11
26
212. 13
30
142. 11
42
1, 142.
(s)
144. 13
44
1,
172.
4,
(s)
144.13
44
1,
175.
4, 920.
214. 11
214. 11
66
66
1,
723.
727.
7,
(s).
(s)
Literature
liquid
3,
835.8
045.
049.
028. 7
497. 8
729.4
729.4
195; cf. 182.

48.
840.0
195; cf. 68.
1,
134. 2
173.
1,
166. 2
173.
1,
166. 2
173.
210.
7, 230. 8
1,
725. 3
10.
1,725.3
10.
3,
4, 780.
906.
(Maleinoid).
C 8 Hig02-
Tetramethylbutenediol
(Fumaroid).
C14H14O2C14H14O2
38
Isohydrobenzoin
The form used
is
16.
(s)
not indicated.
38
1,
See, however, Erlenmeyer,
Ber., 30, p. 1537; 1897.
jr.,
HYDROAROMATIC AND POLYMETHYLENE GLYCOLS

(All types)
Q=26.05Xi^-r-13j+6.5k+3.51
CfiHio0 2 .
Cyclopentanedio 1-1,2
C5H10O2-
Cyclopentanedio 1-1,2
C6H12O2.
C7H14O2.
Cyclohexanediol-1,2 (cis)
Cyclohexanediol-1,2 (trans)..
1-M e t h y 1 c yclohexane-1,2-
C7H14O2-
1-Methylcyclohexane -
C9H10O2-.
CgHioOa..
C10H12O2.
Hydrindene-l,2-diol (cis)
IIydrindene-l,2-diol (trans).
1,2,3,4-Tetrahydronaphtha-
C10H12O2-
102. 08
26
696.1
2,
913.
690.3
237.
102. 08
26
694.2
2,
905. 2
690.3
237.
116. 09
32
32
38
841.6
842.7
992.6
3,
522.
846.3
846.3
999.9
237.
237.
237.
995.1
4, 164.
999.9
237.
098. 5
096. 7
250. 7
4, 597.
1,
4,
2
589. 7
1,
5,
234.
1,
100.
100.
256. 4
237.
237.
237.
(cis) .30
(trans).
12
2-
116.09
130. 11
3, 526.
4, 154.
diol (cis).
1,2
130. 11
38
08
08
164. 09
42
42
48
1,
164. 09
48
1,249.4
5,
228. 7
1,
256.
237.
diol (trans).
lene-l,2-diol
150.
150.
1,
1,
(cis).
lene-l,2-diol (trans).
C10H12O2-
C10H12O2-
C12H16O2-
l-Phenylcyclohexane-1,2-
C12H16O2.
l-Phenylcyclohexane-1,2-
lene-2,3-diol
09
48
1,
250.
5,
235.
1,
256.
237.
164. 09
48
1,
249.
5,
228. 7
1,256.4
237.
192. 12
60
1,
563.
6, 541.
1,
569.
237.
192. 12
60
1,
564.
6,
1,
569. 5
237.
164.
(cis).
lene-2,3-diol (trans).
6
diol (cis).
549.
diol (trans).
38
The
heats of combustion of the acetates and benzoates of these
compounds
are given
below (observer
237):
Trans.
Cis.
Kg-cali5
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
Cyclopentane-1,2 diacetate (lia.)

Cyclopentane-1,2 dibenzoate (s)
Cyclohexane-1,2 diacetate (liq.) _
Cyclohexane-1,2 dibenzoate (s)
1-Methyleyclohexane-l, 2 dibenzoate
Hydrindene-1,2 diacetate
Hydrindene-1, 2 dibenzoate
Tetrahydronaphthalene-1, 2 diacetate (s) ...
Tetrahydronaphthalene-1, 2 dibenzoate
Tetrahydronaphthalene-2,3 dibenzoate.
114.
242.
261.
2, 392.
1,
2,
1,
1,
2,
.
7
5
6
6
Kilojoules
Kg-calis
4, 665.
5,
515. 8 (s)
645. 3
11, 070.
797.
11, 708. 8
6,
343. 6
2,
114.
240.
263.
2, 388.
2, 545.
1, 519.
2, 647.
1, 667.
2, 798.
2, 799.
4, 662.
1,
384. 9
279. 8
10, 013.
9,
2,
1,
Kilojoules
3
4
7
3 (liq.)
287.
9, 996.
10, 651.
6, 358.
3
7
976.
5,
2
3
11,078 1
6,
11, 710.
9, 375.
11, 716.
Bureau
382
[Vol $

CHO COMPOUNDS Continued
VIII.
2.
17.
PHENOLS
Q=26.05XiVr +3.5-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
Kg-calis
(calcu-
Kilo-
Kg-cali5
(experi-
joules
mental)
(K.
lated to
J.)
the
Literature
liquid
state)
Phenol
CeHeO..
C H 6 02C Hg02CaH 6 2 6
6
CeHeOs6
7
7
H
H
110.
05
126.
05
o-Cresol
(s).
43
C7H8O2-.
C7H8O2-.
Saligenin
124. 06
Toluhydroquinol
o-Xylenol (s)
CsHioO.
CsHioO.
C 8 H,oO_
7/1-Xylenol
p-Xylenol
C9H12O
CioH 8 0_.
CioHsO-
(s)
/3-Naphthol
/Thymol
\Thymol
(s)
(s)
Pseudocumenol
a-Naphthol (s)
CioHhO.
124.06
124. 06
122. 08
122. 08
122. 08
(s)
150. 11
Thymohydroquinol
C2iHi 6
/3-Dioxydinaphthylmethane 300.13
Carvacrol
191. 2
1, 185. 4
1, 187. 2
1, 353. 4
1, 349. 7
1,
52
150. 11
166. 11
210. 08
(s)
Phenanthrahydroquinol
3,
035.
1, 037. 4
1, 035. 3
(s)
CioHhO.
CioHh0 2
CHH10O2
2,
617. 3
882. 6
1,
144.06
(s)
638.7
845.4
835.1
136. 10
144. 06
(s).
3,
880.5
895.1
882.5
880.0
824.3
108. 06
108. 06
j>-Cresol (s).
Orcinol (s)__
732.2
684.8
683.0
682.9
683.7
1,
354. 5
307.
600.
2,
475. 8
1,
1,
064.
865. 9
2,858.4
2, 857. 9
2, 859. 2
2,
672. 9
2,583.4
693. 7
3, 680. 7
879.5
108. 06
7/1-Cresol
2-
126. 05
108. 06
108. 06
(s).
(s)
p-Cresol
0__
Hydroquinol
'o-Cresol
C 7 H 8 0._
C
C
110. 05
110. 05
Pyrogallol (s)
Phloroglucinol
C H 03C 7 H 8 0__
6
94.05
(s)
Pyrocatechol (s).
Resorcinol (s)
684. 9
746.
693.
3. 682.
3, 449. 7
3,
732.9
684.3
684.3
684.3
195; cf. 30.

195.
195.
195.
225; cf. 30,
180.
635.7
635.7
885.7
195; cf. 30.

202.
201.
201.
885.7
201.
211.
211.
211.
201.
3,
885.7
3,
3, 535.
837.1
846.6
837.1
494.
331.
4, 341. 5
4, 332. 7
3,
4,
4,
1,
1,
1,
960.
968. 4
1,
4, 985.
4.
1,
1,
1,
038. 5
038. 5
038. 5
44.
225.
201.
201.
201.
191. 3
188. 8
188. 8
351.
201.
225.
225.
201.
201.
668. 6
470. 2
696. 4
1,
1,
351.
302. 5
602. 6
201.
225.
225.
10, 353. 8
2,
474. 8
60.
5,
5,
6,
1,
(s).
2
(s).
The determinations by (202) were carried out in oxygen at ordinary pressure and differ greatly from
by (195). Thus, (202) give for pyrogallol 616.3 kg-calis, but (195) give 639.0 kg-calis
per mole. The above value for phloroglucinol is undoubtedly very low. It should be approximately
the same as that for pyrogallol.
41 It is quite possible that the same objection and the inherent error in the determinations occur also
in the values of (201) as occur in (202). See footnote 40.
42 This value is undoubtedly too high.
43 M. F. Barker, J. Phys. Chem.
29, p. 1350, 1925, reports the following values for the three cresols at
constant pressure: o-(s), 883.7; p-(s), 885.0; m-(liq.), 883.0. However, no experimental details are available except the final values.
4
later determinations
18.
ALIPHATIC ETHERS
Q=26.05XiV+19.5
Dimethyl ether
C2H60
C3H80
C4H60
(g)
Methylethyl ether (v)

Methylpropargyl ether
(v)
_ _
Methylallyl ether (v)

/Diethyl ether
\Diethyl ether (v)
CYfiioO
C6H10OC6H10O2
Diallyl ether (v)
Acetylacetone-O-methyl
46
60
70.00
72.00
74.08
18
08
32
30
118. 11
128. 10
158. 17
34
36
60
98
114.
347.6
503.4
600.8
623.9
651.7
660.3
12
20
22
24
1,
453. 7
2, 105.
512.
2, 609.
2, 727.
2, 763.
2,
223; cf. 10.

223.
223.
223.
204.
204.
2
6
2
4
4
906.6
817.8
3,
3,
791. 4
422. 5
924.6
968.0
3,
869. 5
609. 3
6,
820.5
223.
166.
ether.
C6H14O2C7H12O2
C]0E22O
44
For heat
Glycoldiethyl ether .
Acetylacetone-O-ethyl ether
of
combustion
1,
of diethylene glycol, see footnote (37), p. 380.
4, 051.
730.
1,
924.7
976.8
172.
166.
582.
65.
383
Kharasch]
VIII.
2.
ALIPHATIC ACETALS
19.
Q=26.05XN+19.5X0
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
(experi-
Kilojoules
mental)
(K.
Kg-calis
Kg-calis
(calcu-
lated to
the
J.)
Literature
liquid
state)
CsHeOz.
Glycolmethylal (Methyleneethylene dioxide).
74.05
C3EUO2C4H6O2-
Methylal
76.06
88.06
462.8
559.2
2,
90.09
106.0
620.0
(Ethylidene-
Glycolacetal
715. 43
1,
403.7 59.
936. 8
340. 3
455.8
560.1
26.
2,
594. 7
2, 495.
612.1
579.5
58.
241. 3
3, 238. 4
768.2
58.
103.
862.
897.
848.
924.7
1,
59.
acetal of glycol).
Dimethylacetal
Methyl orthoformate
C4H10O2C4H10O3-
(v)
C5H12O2.
D iethylmethylal
104. 10
C Hh02-
Diethylacetal.
118. 11
6 H,o04C7H16O2-
CvHhObC 8 Hm04.
596. 8
3,
774, 5
773. 8
923.0
931.2
919.5
3,
34
Erythritemethylal (s).
Dipropylmethylal
a-Methylglycoside (s).
146. 08
132. 13
194. 11
1,
Erythritediacetal
174. 11
1,
745.
085. 9
'
842.5
3,
3,
117.
3, 117.
4, 544. 5
3, 529. 2
4, 392. 2
1,
081.
1,
087. 9
393. 6
DiisobutylmethylaL .
160. 16
1,
C9H14O6-
Mannitetrimethylal
218. 11
1,
084.
4, 536.
1,074.4
19
16
18
17
1,
708. 7
539.
7,
150.
1,
706.
6,
440. 7
494.
218. 7
1,
1,
791. 4
726.
212. 19
1,
947. 7
CnH 2 40 2 .
C12H20O6.
C12H22O2C12H22O4-
(s).
Diisoamylmethylal
Mannitetriacetal
(s)
Amylpropiolic acetal
Diacetal of acetylenedialde-
hyde
C13H24O2-
188.
260.
198.
230.
1,
839. 3
7,
1,
790. 7
724.
1,
946.
8, 145.
1,
7,
58.
241.
C9H20O2-
5,
157.
58.
049. 5
395. 3
(s)...
223.
1,
59.
58.
138.
138.
(s).
Hexylpropiolic acetal
The values
46
i7
for acetals given by (58 and 59) are about 0.5 per cent to 1.0 per cent too high.
Individual determinations do not agree better than 0.5 per cent.
The values of (103) are about 0.6 per cent too high. Better value, 769.2 kg-cal u.
(C 2 H 5 0)2
H
H
C-C=C-C
(OC 2 H 5)
2.
20.
AROMATIC ETHERS
Q=26.05XiV+19.5
0..
Anisole_
108.
06
34
905.
900.
/ 1,056.9
I 1, 060. 3
1, 057.
4, 423.
3,
3,
905.2
787. 8
770. 3
1,
061. 5
106.
203.
203.
211.
203.
CgHioO _.
Phenetole
122.
08
40
CgHioO..
m-Cresolmethyl ether.
122. 08
40
C 8 H l0 O 2 -
Hydroquinoldimethyl ether
138. 08
38
1,
014. 7
4, 246.
C 8 HioOa.
Resorcinoldimethyl ether
Phensdpropyl ether
>-Cresolethyl ether
m-Xylenolmethyl ether
38
46
46
46
1,
C9H12O..
08
136. 10
136. 10
136. 10
022. 6
213.
212. 8
213. 4
162. 08
46
46
50
1,
244.
233. 9
334. 6
5,
1,
324.
314. 7
5,
286. 6
277. 6
286. 4
5,
384. 4
346.
383. 6
1,
5,
727. 6
1,
1,
366. 1
455. 2
203.
057. 4
1,
452. 2
196,
4,
4,
437. 4
423. 6
"I,~058.~5"
1,
028. 9
203.
4, 279.
1,
5,
1,
5,
6
076. 8
075. 6
203.
203,
203.
5,
078.
1,
028.
217.
214. 3
210.
206. 6
5, 163. 9
5, 585. 3
1,
542. 6
507. 3
1,
(s).
C9H12O.
C9H12OCioHjoOa.
C10H10O2.
C10H12O..
Safrole
Isosafrole
Methylchavicole
(p-Ally-
138.
162. 08
148. 10
1,
1,
1,
1,
1,
1,
203.
246. 8
243. 8
190.
1,331.5
193.
331. 5
328. 5
196.
163.
1,
19fl.
lanisole)
C10H12O..
C10H12O..
Anethole (s)
a-Ethoxystyrene.
148. 10
148. 10
50
50
CioH) 2 02-
Eugenol
CWH12O2-
Isoeus;enol
AIlyl-3,4-guaiacol (Betelphe
164. 10
164. 10
164. 10
48
48
48
CinH; 2
2_
1,
1,
1,
1,
5,
5,
1,
1,
1,
282. 9
279. 9
282. 9
nol).
C10H14O..
C n Hi 4 2 .
p-Xylenolethyl ether
Methyleugenol
150. 11
178. 11
52
54
1,
368. 6
458. 6
5,
CuHmOj.
Methylisoeugenol
178. 11
54
1,447.4
6,
1,
6, 104.
195.
384
Bureau

VIII.
2.
AROMATIC ETHERS Continued
20.
Q=20.05XiV+19.5
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
Kg-calis
(calcu-
lated to
J.)
(N)
CnHieO-
Thymolmethyl
C12H14O4
C12H14O4
Isoapiole
Apiole
C12H16O2
C12H16O3
ether
_. ..
(s)
(s)
Asarone(s) 4 9(Propenyl-2,4,5trimethoxy benzene)
C12H18O
C16H16O2
Thymolethyl ether
C21H16O2
C22H1SO
/S-Naphtholformal
Di-p-methoxystilbene
(s)
(s)
Methyl ether
of diphenylphenylethinyl carbinol. 50
Ethyl ether of diphenylphenylethinyl carbinol.
Propyl ether of diphenylphenylethinyl carbinol.
C23H20O
C24H22O
the
liquid
Literature
state)
1,
272. 5
228.
1,
164. 13
222. 11
222. 11
58
54
54
1.
192. 13
208. 13
60
58
1,
178. 14
240. 14
64
76
2,
300.13
298.14
96
2, 500.
10, 457.
2,
104
2, 739.
11, 456. 2
312. 16
110
2. 891.
326. 17
116
3,
047.
1.
1,
1,
1.
524.
498.
488. 2
6, 379.
602. 3
576. 2
6, 705.
679.
016. 6
523.
494. 2
491. 2
203.
196.
196.
608. 5
575.
196.
196.
679. 7
018.
203.
104.
513.
748. 3
60.
2,
12. 091.
2,
904.
95.
12, 744.
3,
060. 9
95.
6,
6,
1,
1,
6,
596.
1,
7,
030. 4
433. 4
2,
8,
1,
95.
(CH 3 0) 3 ( 2 .*. 5 ) (C 6 H 2 ) (CH = CH. CH3) 0)

(C6H5)2.C(OCH3)C = C.C6H 5
.
21.
ETHYLENE OXIDES
(a-Oxides)
fEthylene oxide (v)_

(.Ethylene oxide .
a-Propvlene oxide 51
/S-Methyl-,8, 7-butene oxide
(a-Dirnethyltrirnethylene
C2H40
C3H80
CsHioO__
44.03
10
58.05
86.08
16
2S
308.4
302.1
451.1
749.8
100. 10
132. 06
34
42
913.9
1,116.8
7
3
9
9
245.
245.
824. 7
673. 8
245.
236.
290.
264.
887.
3, 137.
1,
1,
1,
16; cf. 223.
oxide). 52
C6H[20
CsHgO...
51
CH2.
-y,5-Hexylene oxide
53
3,
4,
C-CH3.
\ /
(CHs)
CHs.
C - C - CH3.
CHY C - C - CH CH
2.
3.
ALIPHATIC ALDEHYDES
22.
[Also those aromatic aldehydes in
which the aldehyde group
is
not attached to the aromatic nucleus]
Q=26.05XiV+13.0
CH20
i (CH 2 0) n
h
(CH
0) 3
C2H4O
Formaldehyde (g)
Paraformaldehyde
30.02
()
a-Trioxymethylene
Acetaldehyde
(s) .
..
(v)
C2H4O..
C2H2O2--
C3H5O
54
Glvoxal (s) .
Propionaldehyde
Propionaldehyde
-..-
No great reliance can be put upon
available.
The information
561.2
239.
122.
511.0
239;
54
109. 5
458.3
239; cf.56.
44
44.03
10
10
280.5
279.0
58.02
172.3
438.4
434.2
58
58.05
(v)
134.1
1,
1,
1,
1,
173.
166. 8
279.5
273.5
223; cf.39.
720.6
833. 4
815. 8
182.3
429.8
429.8
69.
25.
223.
25.
the above values until the exact details of the determinations
in the article
is
cf. 56.
extremely meager and insufficient.
become
Kharasch]
2.

22.
ALIPHATIC ALDEHYDES Continued
VIII.
[Also those aromatic aldehydes in
which the aldehyde group
is
385
not attached to the aromatic nucleus]
Q=26.05X-Ar+13.0
NumMolec-
Name
Formula
ular
weight
ber
Kg-calis
of
elec-
trons
Kg-calis
(calculated to
Kilo-
(experi-
joules
mental)
(K.
the
J.)
(N)
O3H4O
Acrolein
(C 3 H40) 3
C4H6O
C4H8O
56.03
168. 09
14
Literature
liquid
state)
389.
393.
/
\
1,
1,
22
20
168. 8
542.1
596.8
546.6
4,
70.05
72
88.06
1,
"""20"
2,
629. 3
646. 4
891. 4
267.
495. 8
285. 9
C4H8O2
Isobutyraldehyde (v)
/S-Hydroxybutyraldehyde
C5H10O
Valeraldehyde_
86.08
28
742.0
3, 103.
C5H4O2
Furol (Furfural dehyde)
96.03
20
559. 5
2,
812.8
805.6
814.0
3,
2,
2,
390.7
141.
547.0
586.1
540.5
238.
117.
223.
118.
(Aldol).
C6H12O3
132. 10
132. 10
/Metal dehyde (s)

(Metaldehyde. _ _
(C2H4CO3
CgHeO
CqHsO
w-Heptaldehyde (Oenanthol).
Phenylpropiolic aldehyde
Cinnamic aldehyde .
C10H16O
Citral (Geranial)-
C7H14O
114.
130.
132.
152.
ii
05
06
13
40
40
42
54
742.4
339. 8
3, 399.
3, 371. 4
118.
126.
126.
406. 6
062. 4
081.
4, 442.
1,
4, 520.
1,
1,112.3
4, 655.
1,
1,
1,
437.
6,
055.
081. 6
1,113.6
019. 6
113.
44.
1,
445. 7
110.
138.
183.
174.
AROMATIC ALDEHYDES
23.
Q=26.05XAr+13-3.5a+3.5m
CtHcO.
Benzaldehyde
o-Hy droxybe nzaldehyde
02
106.05
122. 05
32
30
841.3
796.0
3, 520.
328.
843.1
794.5
205.
3,
(Salicylaldehyde).
C7H6O2
C7H6O2
p-Hydroxybenzaldehyde (s)
ra-Hydroxybenzaldehyde (s)
122. 05
122. 05
30
30
792.7
788.7
3,
315.
303.
794.5
794.5
62.
3,
CsHsOs
Vanillin
152. 06
34
914.1
3,
825.
918.2
183.
CsHeOs
(3-Methoxy-4hydroxybenzaklehyde)
Piperonal (s) (Methylenepro-
882.1
C14H10C
Disalicylic aldehyde
641.
3, 647.
6, 645. 2
(s)
tocateehuic aldehyde)
C3H0O
Acetone (v)_
C3HGO..
Acetone
226. 08
(s).
870.
870.
1, 589.
which the ketone group is not attached

Q=26.05XiV+6.5
.._
58
16
58.05
16
/
I
C4H80
Methyl ethyl ketone
C4H0O2
Diacetyl
02-
CoHioO
C5H10O
C5H10O
CsHioO
CoHioO
C 6 HioO
CeHioO
C 6 Hio0
C Hi
6
65
of
72.06
86.05
22
18
_
Acetylacetone 56
-_
Diethyl ketone.
Methyl propyl ketone (v).._
Methyl propyl ketone
Methyl isopropyl ketone
100. 06
86.08
86
86.08
86.08
24
28
28
28
28
Ethvl allyl ketone

Mesityl oxide
98.08
98.08
98.08
114. 08
65
Allylacetone
f
2
12
The author
Methylacetylacetone
Pinacolin (s) (Methyl
butyl ketone)
tert.-
Methyl butyl ketone

(94) gives
See also p. 382 for O-methyl

57
Evidently this value by (78)
acetylacetone.
and ethyl
is
183.
163.
157.
too low.
to the aromatic nucleus]
435.8
1,
430.
426.
1,
582.3
503.3
822. 5
801. 2
784. 9
223.
423.3
64.
2,435.2
2, 104. 8
579.6
215.
575. 7
638.2
735.6
215; cf. 116.
076. 3
069. 2
735.6
735.6
223.
215.
215.
162.
117.
162.
166.
215.
1,
59.
94.
615.
2,
735.6
750.4
735.6
733.9
3, 076.
32
32
32
30
857.1
846.7
856.7
798.5
792.6
3,
590.
543.
3. 588.
3, 341.
3, 317.
4
4
7
853.1
853.1
866.1
794.5
100. 10
34
891.8
3, 729.
892.2
100. 10
34
895.2
3, 743.
892.2
\ After several distillations
only the final value

this observer are about 0.5 per cent too low.
5C
3,
ALIPHATIC KETONES
2*.
[Also those ketones in
}l50. 05
32 J
103.
for this
3, 138.
3,
3,
3,
compound, and no other information.
78.
215.
The
values
ethers.
Compare the rather good agreement
in the case of the
methyl-
386

VIII.
2.
[Vol.8

ALIPHATIC KETONES Continued
which the ketone group is not attached to the aromatic nucleus]
Q=26.05XiV+6.5
24.
[Also those ketones in
NumMolec-
Name
Formula
ular
weight
Kg-cahs
ber
Kg-cali5
Kilo-
(experi-
joules
mental)
(K.
of
elec-
trons
(calcu-
J.)
Dipropyl ketone
Diisopropyl ketone
Methyl hexyl ketone
40
40
46
1,
128. 13
138. 11
190. 05
144. 06
48
38
46
1,
Acetylphenylaeetylene
C10H8O4-.
Furoin
192. 06
40
C10H10O
C11H10O
C11H12O
C11H12O
Propionylphenylacetylene 68 _
a-Methyl-a-benzalacetone.
08
08
160. 10
160. 10
48
52
54
C12H12O
Butyryiphenylacetylene
172. 10
58
Propionylphenybutine
186.
186.
192.
200.
C9H14O
C10H6O4
CioH 8 0_
_.
114. 11
114.11
(s)
a-Methyl-a-benzalacetone
146.
158.
Literature
state)
(JV)
C7H14OC7H14O
CsHieO
lated to
the
liquid
1,
1,
1,
1,
050.
045. 5
205.
4, 393.
2
3
1,
5,
039. 7
1,
048. 5
048. 5
204.
280. 7
064.
235.
5,
364. 8
1,
282.
1,
231.
/ 1,097.7
I 1, 114.
1,
257.
385.
417.
413.
1,
537.
1,
1,
1,
54
4
5
7
4, 372.
4, 454.
5, 164.
1,
215; cf. 116.

116.
215.
171.
8.
4, 593.
138.
241.
4, 662.
8.
1,
794. 2
5, 933.
5, 915. 5
1,
6,
431.
7,
052. 5
195.
754. 7
667. 3
737.
5, 262.
5,
1,
266. 4
387. 7
419. 7
419.
183.
138.
166.
166.
1,
544.
138.
1,
703.
700.
868.
856.
103.
1,
(s).
C13H14O
.__
CisHhO
59
Iso valerylphenylacetylene . .
C13H20O
C,4H 16
Caproylphenylacetylene
C17H14O
11
11
16
13
234. 11
64
1, 686. 4
64 38.001,720.5
70
1,851.2
70 " 1,833.4
80
2, 087. 9
7,
7,
7,
8,
1,
1,
1,
2,
5
6
5
138.
138.
162.
138.
183.
58 The experimental values of the compounds marked show such wide variations for members of an
homologous series that undoubtedly it is the fault of the experimenter. The difficulties of obtaining these
substances in pure condition may have had something to do with it. Consult original paper.
C6H 5 .CH2CH2.C=C-COC 2 H5.
60 The author (138) claims that this compound behaves abnormally in many respects.
25.
AROMATIC KETONES
Q=26.05XiV+6.5-3.5a-6.5b
CgHgO
C13II10O
Acetophenone (s)_
Benzophenone (s).
120. 06
182. 08
38
60
C14H10O2
Benzil
210. 08
62
C14H10O4C14H1JO2.
C, 5 HioO..
CsiHioO..
Benzoyl peroxide (s)

Benzoin (s)
Benzoyiphenylacetylene (s)
/8-Phenylbenzalacetophe-
C21H18O2.
J,/3-Diphenyl-/3-hydroxy-
(s)
242.
212.
206.
284.
08
10 "'hi'
08
68
12
98
988.9
4, 138.
1,
556. 5
6, 514.
1,
624.
6,
61 1,
551.
992.9
183
562.
1,627.6
206; cf. 183,

95.
182; cf. 94.
787. 2
2, 545. 3
500.
6, 994. 8
7, 474.
10, 644. 4
673. 2
801.
2, 555.
163.
182.
138.
95.
538.
10,613.9
2, 555.
95.
1,671.4
1,
1,
798.
6,
1,
1,
none. 62
302. 15
98
2,
propiophenone.
61 Compare W. A. Roth and R. Lasse, Z. Electrochem.,
These authors, using a micro30, p. 607; 1924.
combustion apparatus, obtained values for this substance which varied within 2 per cent. This discrepancy is due to the fact that the substance does not burn completely and always leaves varying amounts
of unburned carbon.
62
(C
H5)2:C:C~C-C6H 5
O
26.
QUINONES
Q=26.05XiV+33.1-3.5a-6.5b
C6H4O2-
Quinone
(s) 6J_
108. 03
24
656.
656.
C7H6O2C10H6O2-
CioH 6 2
CioH l2 02
Ci4Hs0 2
Toluquinone (s)
a-Naphthoquinone
(s).
/3-Naphthoquinone
(s)
Thymoquinone
(s)
C14H8O2
Anthraquinone (s)
Phenanthraquinone
CuHsOs
Monohydroxyanthraquinone (s).
combustion
63 The heat of
kg-cahs per mole.
of
(s)
quinhydrone
is
803.2
158. 05
30
42
1,
158.05
158.
05
164.10
164.
10
208.06
208.
06
208.06
208.
06
224.06
224.
06
42
48
60
60
58
1,106.4
106. 4
1,
271. 3
1,271.3
1,
1,544.5
1, 544. 5
1,544.0
1, 544.
1,481.7
1, 481. 7
122. 05
given
by
(180), Z.
100. 8
2,
2,
746. 6
747. 9
658.3
225.
180;
cf. 30,
43, 222.
361.
4, 606.
225;
225;
cf.
1,
811.1
114. 2
630. 3
4,630.3
4,
5,320.4
320. 4
5,
6,463.7
6, 463. 7
461. 6
6,461.6
6,
200. 9
6,200.9
6,
114. 2
1,114.2
1,
276. 5
1,276.5
1,
1,562.0
1, 562.
1,562.5
1, 562. 5
513. 4
1,513.4
1,
225;
225;
225;
225;
225;
cf.
3,
Phys. Chem.,
cf.
222.
222.
222.
222.
222.
cf. 222.
cf. 222.
cf.
cf.
117, p. 57, 1925, as 1,334.5
Kharasch]
387

2. CHO COMPOUNDS Continued
VIII.
26.
QUIN ONES Continued
Q=26.05X-/V+33.1-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
of
elec-
trons
(calcu-
Kg-calu
Kilo-
(experi-
joules
mental)
(K.
lated to
J.)
the
Literature
liquid
state)
(JV)
CuHgOi
1,2-Dihydroxyanthraquinone (s) (Alizarin).
240. 06
58
1,
448.
6,
063.
1,
464.
225; cf. 222.
CmHsOj
1,2,4-Trihydroxyanthraquinone (Purpurin).
256. 06
54
1,
402.
5,
867. 8
1,
416. 2
225; cf. 222.
7-Hexahydroxy-
304. 06
48
1,
249.
5,
227. 5
1,
268.
225; cf. 222.
264. 13
84
2, 152.
9,
007.
2,
187. 7
225; cf. 222.
ChH
1, 2, 3, 5, 6,
anthraquinone
(s)
(Rufi-
gallic acid)
Retenequinone (s) (Methylisopropylphenanthraqui-
Ci 8 Hi 8 02
none)
27.
HYDROAROMATIC AND POLYMETHYLENE KETONES

Q=26.05XiV+6.5
Acetyltrimethylene
Cyclopentanone
/3-Methylcyclopentanone
Acetylcyclobutane
84.06
84.06
98.08
98.08
98.08
26
26
32
32
36
112. 10
112. 10
38
38
112. 10
112. 10
124. 10
38
38
42
1,
126. 11
44
132. 06
132. 06
138. 11
42
42
48
s-/3-Hy drindanone
138. 11
frans-/S-Hydrindanone_
1,4-Methylacetylcyclohexane
Ethylcyclohexyl ketone. _
138. 11
140. 11
3-Methylcyclohexene-2-
"
691.4
682.0
2,
833. 4
3,
856.8
942.9
3,
2,
3,
891.
852.
485. 3
583.
943. 2
956.~8~
215.
163.
215.
215.
149.
996.4
996.4
215.
215.
996.4
996.4
215.
215.
215.
683.8
840.1
one-1.
E thyl-l-cyclopentanone-2_
1,3-Dimethylcyelopenta-
990.4
989.8
4, 141.
4, 139.
994.8
996.7
102. 2
4, 160.
4, 168.
1,
152.
1,
1,
086. 9
088. 3
248. 4
48
1,
48
48
50
50
52
1,
52
54
54
1,
none-2.
/3-Methylcyclohexanone
Cycloheptanone (Suberone).
1,3-Dimethylcyclohesene-
609. 4
1,
4, 826.
1,
152. 7
163.
4, 548.
1,
554. 5
220. 8
1,
1,
093. 6
093. 6
263.
236.
236.
215.
218.
5,
223. 3
1,
256. 9
83.
243.
267. 8
5,
1,
1,289.5
5,
278. 3
374. 4
5,
202.
301.
392.
345.
751.
256. 9
256. 9
309.
309.
380. 6
215.
215.
215.
201.
373.
404. 4
402.
397.
5,
4,
107.
6-one-5.
1,1-Dimethylcyclohexanone-2.
a-Indanone
/3-Indanone
1,1,5-Trimethylcyclohexene-
1,
4,
5-one-3.
Methylcycloheptyl ketone
140. 11
140. 11
Carvone
150. 11
Eucarvone
150. 11
152. 13
ds-/S-Decalone
fr ans-/S-Decalone
1,
8
2
7
2
1,
426. 2
1,
419. 7
5,915.3
1,
933. 3
1,
426. 2
426. 2
419. 7
5,
1,
412. 2
423. 7
Carvenone
152. 13
1,407.9
54 /
\ 1,417.0
5,
Dihydroeucarvone_
152. 13
152. 13
152. 13
Camphor
152. 13
correction of
(s)
54
54
54
54
54
192. 16
192. 16
per cent applied to (215) values
70
70
is
1,
1,
65 1,
412.
416.
430. 4
427. 6
/ 1,411.0
\ 1,410.8
1,
1,
835. 4
839. 9
5,
5,
5.
905.
958.
897.
930.
values about 0.6 per cent too high.
1,
374.
413. 2
1,413.2
974. 5
1,
910. 7
904. 2
1,413.2
5
7, 707. 3
162.
50.
5,
7, 688.
215.
50; cf. 162.
5,
5,
175.
169.
169.
50.
5,991.9
evidently too large.
0.6 per cent.

(50) gives
1,
1,
1,
1,
152. 13
1,
1,
54 /
1,
1,
7
9
152. 13
/3-Ionone.
The author
1,
751. 9
5, 877.
5, 867. 8
5, 842. 7
5,
152. 13
a-Ionone
The
1,
5,
Carone
Thujone
65
1,
Dihydrocarvone.
Pulegone
Isopulegone
64
152. 13
1,
1,
1,
849. 5
849. 5
174.
162.
175.
50.
125.
217;
cf. 175,
183, 70.
174.
174.
Roth recommends about
388
Bureau
lvoi.fi

VIII.
2.
CARBOHYDRATES
28.
(Monosaccharides)
Q=26.05XAr+13q+13j+6.5k+3.51
NumMolec-
Name
Formula
ular
weight
ber
(experi-
Kilojoules
mental)
(K.
Kg-cali5
of
elec-
trons
Kg-cali5
(calcu-
lated to
J.)
the
liquid
Literature
state)
C5H10O5
Arabinose
C5H10O5
Xylose
CeHioOs
Levoglucosan
C6H12O5
Rhamnose
(s).
150. 08
20 /
08
20 /
558.
559.
561.
560.
\
(s)
150.
26 /
2
2
3
7
2
004.
006.
977.
979.
816,
827.
805.
796.
801.
806.
2,
2,
677.7
162. 08
(s)
335.
343.
350.
2, 345.
2, 836.
2,
717.
718.
3,
711.5
711.9
673.0
2,
(s)
164. 10
Fucose (s). __
_ ...
d-Glucose (s) (Dextrose)
182. 11
164. 10
180. 10
CeHÔe
C Hi20
C6H12O6
Z-Fructose
180. 10
24 /
675.
2,
24
671.0
668.3
2,
180. 10
Galactose (s)__.
180. 10
24 /
\
669.
670.
2,
C7H14O7
Ci2Hi 8 8
Glucoheptose
210.
290.
390.
390.
11
28
783.5
3,
14
17
17
50
64
64
350. 5
726. 3
725. 5
5,
C6H12O5.H0O
C6H12O5
C 6 Hi 2 06
(s)
~~~26~
24
Sorbinose
_,
C16H22O11
C16H22O11
(s)
Rhamnose
(^-Sorbose)
(s)
triacetate
(s)
07
Pentaacetylglucose (s)
Pentaacetylgalactose (s)
1.
1,
1,
3,
2,
2,
2,
2,
7,
7,
566.5
"~~566.T
87.
722.8
195.
3
5
722.8
677.2
195.
195.
182; cf. 195,
64, 87.
677.2
195.68
677.2
677.2
195.
195.
9
9
276. 6
647. 8
219. 4
216.
87; cf. 48.
787.9
1,354.5
1,
1,
66 The heat of combustion of benzoic acid obtained by these investigators is about

than the present international value. Their results are therefore uniformly too high.
07 For the method of calculating these compounds, consult the formula fur esters.
29.
195.
87; cf. 31.
183.
725. 7
725. 7
68.
87.
87.36
87.
0.2 per cent higher
DISACCHARIDES
Q=26.05XiV+19.5o+13j+6.5k+3.5l+13q
C12H22O11.
Cane sugar
C12H22O1
Milk sugar
(Sucrose).
(s)
(anhydr.)
342. 18
48
1,
349. 6
5,
648. 3
1,
350.
5,
658. 1
1,
344. 7
5,
627. 6
1,
350. 2
5,
\ 1,351.3
5,
649. 8
655. 2
(s)
(Lactose).
C12H22O11.H2O.
Lactose (cryst.)
C12H22O11
Maltose
360. 19
(s)
342. 18
(s)
Ci2H 20 n .H 2 0- Maltose (cryst.)

Trehalose (s) (Mycose)
C 12 H220 U
2
C12H22O11.2H2O
C12H22O11
C28H38O19
C2SH38O19
C28H38O19
C28H38O19
68
The author
Trehalose (cryst.)
Cellobiose (s) (anhydr.)
Sucrose octaacetate
Maltose octaacetate
(s)
(s)
Cellobiose octaacetate (s)

Lactose octaacetate (s).
(181)
360.
342.
378.
342.
19
18
21
18
678.3
678.3
678.3
678.3
used the potassium chlorate method.
1,
1,
1,
1,
3,
3,
3,
3,
339.
349.
341.
349.
033.
030.
032.
029.
5,
5,
5,
230.5; Cj .80
52,
67,
237,
9,
172,
3,
241, 195,
234, 153,
87.
195; cf 87,
181,6 74,
88.
195; cf 64,
150, 46.
195.
87.
6
2
2
3
87.
3
6
12, 694. 4
87.
12, 683.
87.
12, 691. 5
87.
12, 677. 7
87.
The value
is
604.
647.
614.
5, 649.
unreliable.
195; cf. 64.

183.
183.
Kharasch]
389

VIII.
TBI,
30.
TETRA, AND POLYSACCHARIDES

NumMolec-
Name
Formula
ular
weight
Kg-cali 5
ber
of
elec-
trons
Kg-calis
Kilo-
(experi-
joules
mental)
(K.
(calcu-
lated to
the
J.)
Literature
liquid
state)
C18H32O16
C18H32O18.5H2O
C18H32O16.H2O
C24H42O21-
Raffinose (s) (Melitose)

Raffinose (cryst.).
Stachyose
(anhydrous)
(s)
504.
594.
522.
664.
26
34
28
34
2,
::::::
2,
2,
2,
195; cf. 31.

195.
195.
87.
025. 5
018. 9
042.
708. 7
476. 7
449. 1
545. 8
11, 335. 9
17, 488. 3
195.
18, 828. 3
87.
17, 283. 6
195.
8,
8,
8,
calc.
4, 178.
Starch acetate..
4,
499.
4, 129.
\ 4, 190.
4,522
Cellulose.
Xylan
Xylan
"
..
acetate
18, 924.
.6
17, 191. 6
4,
9
188. 8
17, 521. 8
17, 496. 6
4, 180.
17, 535.
4, 107.
87.
195.
207; cf. 64,
75, 133.
195; cf. 76.
8
9
4, 496.
18, 815.
4, 243.
17, 756.
4, 548.
19, 033. 4
87.
87.
87.71
68 W. K. Slater gives as the heat of combustion of the dry monohydrate C6H10O5.H2O,

3,836X4.182 joules
per gram; Biochem. J., 18, p. 629; 1924. The authors (133), on the other hand, report the following values
mean heats of combustion of glycogen from Mytilus and from frog muscle, per gram: Anhydreus
glycogen, 4,238; hydrate 4,214; dissolved glycogen, 4,202.
of the
7
More probable
?i
These authors
value, 4,260.0
also give the values for diamylose, a-tetramylose, /S-hexamylose, a-octamylose.
31.
ALIPHATIC ACIDS
(Saturated monobasic)
Q= 26.05 XiV
CH2O2--.
("Formic acid
(Formic acid
62.8
46.02
73
C2H4O2-.
Acetic acid
60.03
C3H6O2-.
Propionic acid
74.05
62. 6
209.
207.
367. 2
C4H8O2-C4H8O2--
w-Butyric acid
524.3
517.4
681.6
'
C5H10O2-.
Isobutyric acid
%- Valeric acid
88.06
88.06
102. 08
C6H12O2-.
Caproic acid
116. 10
'
C6H12O2-.
Isobutylacetic acid
116. 10
C6H12O2-.
Diethylacetic acid
116. 10
'
C7H14O2-.
C7H14O2-.
Ethylpropylacetic acid.
Heptylic acid
130. 11
130. 11
C Hi
Dipropylacetic acid.
144. 13
acid
158. 14
2 -,
Heptylacetic
C10H20O2.
C11H22O2.
Capric acid (s)

Undecylic acid
C12H24O2
C14H28O2
Laurie acid (s)

Myristic acid (s)
C16H32O2
Palmitic acid
C18H36O2
Stearic acid
C20H40O2
C22H44O2
Arachidic acid
(s) .
172. 16
186. 18
Behenic acid
__.
284. 29
(s)
312. 32
340. 35
(s) .
192; cf. 118.
2,
2
163. 8
2,
852. 5
521.0
521.0
677.3
192; cf. 77.

117.
192.
3,
475. 2
511. 2
833.6
215.
66; cf. 115.
192.
227.
192.
192.
227.
837.4
3,
833.1
3,
3,
4
5
9
833J
837.4
994.5
986.1
504.
474.
504.
4, 161.
4, 123.
830.
1,
479. 8
1,
458. 8
615.
2,
771.
084.
396. 6
193.
193.
192.74a
2,
709. 2
3,
13, 971. 2
3,
021. 8
334. 4
458.
615. 9
6, 762.
771.
085. 8
398. 4
2, 384. 6
2,
697. 7
025. 9
3, 338. 4
146. 2
302. 5
192.
192.
120.
192.
192.
5, 383.
'752,711.
128
2, 194.
3,
1,
116
1,
34, 86.
34.
164.
831.
838.
2,
256. 26
L
(s)
364.7
4, 819.
1,
200. 19
228. 22
. . .
536. 7
151. 6
1,
'
(s)
65. 1
1,309.4
1, 287. 4
1,
'
C9H18O2-
262.6
261.8
875.7
866.7
74
at 0).
(liq.
5,
6,
102.
1,
1,
414. 6
729.
2,
10, 037. 3
7,
8,
9,
1,
64.7"
970.
11, 348.
2,
11, 279.
3,
12, 663.
192.
64.
192.
193.
72 The
values of (192) are uniformly about 0.5 to 0.7 per cent higher than the values for the same compounds recorded by modern investigators.
73
The formula for formic and oxalic acids is Q=26.05XiV+13.
74
This value is calculated from Thomsen's data. The figure is more or less uncertain, for the specific heat
value (4.77 cal.) varies considerably with the temperature.
74
See footnote 72.

values of (64) are uniformly 0.2 per cent high, for the value they employed for benzoic acid
than the accepted one by that amount.
See footnote 72,
74b
The
larger
75
was
390
Bureau
[Vol
ft

VIII.
2.
32.
ALIPHATIC ACIDS
(Hydroxy and Keto Acids)

Q=26.05XiV+6.5s+13j+6.5k-f3.51+13u+6.5v-f6.5w
Kg-calis
NumMolec-
Name
Formula
ber
Kg-calis
ular
of
(experi-
weight
elec-
mental)
(calcu-
Kilojoules
(K.
lated to
J.)
trons
C2H2O3.H2O.__ Dihydroxyacetic
acid
(s)
92.03
76.03
88.03
90.05
6
10
12
the
Literature
liquid
state)
125. 5
524.8
130.2
166.6
279.1
697.2
1,
326.
1,
168.
363.
169.3
280.5
325.6
35.
(Glyoxylic acid).
Gly collie acid
C2H4O3
C3H4O3
C3H0O3
(s)
Pyroracemic acid
Lactic acid
__
(s)
77
182
49.
64; cf. 127,
75,
135,
134.78
C4H8O3
Hydroxyisobutyric acid
(s)._
104. 06
18
471.8
1,
973.
481.9
134; cf. 127.
C4H8O3
/3-Hydroxybutyric acid
(Racemic).
(s)
104. 06
18
487.9
2,039.9
475.4
64.
489.7
576.8
2,
049. 4
412. 2
579.6
18.
243.
193.
C5H4O3
C Hs0
5
112. 03
C22H44O4
76
See
method
Levulinic acid (s) (/3-Acetopropionic acid).
116.06
Dihydroxybehenic acid
372. 35
of calculation for formic
(s) _ _
and
"~22~
124
3,
235.
2,
13, 541.
182; cf. 44.
3,
oxalic acids, footnote 73.
This value was obtained by burning a concentrated solution of lactic acid and analyzing the same
carbon and hydrogen.
78 The value was obtained
by burning the ethyl and methyl esters of lactic acid.
77
for
S3.
ALIPHATIC ACIDS (UNSATURATED)

3=26.05X^+13
C3H4O2-.
C4H5O2-.
C 5H
Acrylic acid
Crotonic acid (s)
Tiglic acid (s)
Angelic acid (s)
2 -.
C5H8O2-.
a-/S-Pentenoic acid
/3-7-Pentenoic acid
C5H8O2-.
C 5H 8
73.02
2 -.
C5H8O2-.
C6H8O2-.
Allylacetic acid
Sorbic acid (s).
C6H10O2C10H16O2
C11H20O2
Hydrosorbic acid
Geranic acid
Undecylenic acid
C18H34O2
Oleic acid
C18H34O2
C22H42O2
C22H42O2
79
(s)
100.06
100.06
100. 06
24
24
623.7
632.2
100.06
112. 08
24
28
641.6
743.0
114.08
184. 16
30
52
60
282.27
102
168. 13
(s)__.
Elaidic acid (s)

Brassidic acid (s)
Erucic acid (s)
The above
(s)
79
12
18
24
24
86. 05
100. 06
282. 27
338. 34
338. 34
80
/
\
102
126
126
2,
2,
2,
3,
3,
140; cf. 155.

183.
183.
183.
610. 2
2, 645. 8
638.2
638.2
166.
685.
638.2
755.4
167.
133.
3,
794.5
5,
380. 6
576.
2, 663. 6
G6.
171.
1,
2,
795.4
1,
81 1,
325.6
481.9
631.7
638.2
327. 5
477.7
626.4
634. 8
379.
579. 7
657.
681. 8
664. 2
290.
296. 7
1,
2,
389.
999.
621.
656.
8
2
5
2,
2,
3, 109.
331.
776. 7
611.
11, 108. 9
11, 223. 3
6,
11, 149.
1,
183.
64.
183.
2,
3,
13, 769.
13, 798.
1,
3,
670.
288. 8
295. 3
183.
the mean of two determinations which do not agree better than 0.4 per cent.
of calculating cis-trans isomers, consult formula for maleic acid.
is
For method
81
Mean
value.
34.
ALIPHATIC ACIDS (MONOBASIC)

(Acetylene type)
Q=26.05XiV+33.1h
C4H402
84.03
02
Amy lpropiolic acid
C9HHO2
CnHisO.
Hexylpropiolic acid
Undecolic acid( s)
140. 09
154, 11
182. 14
16
40
46
58
C18H32O2
C22H40O2
Behenolic acid
280. 26
336. 32
100
124
C H
8
12
(s)
1,
452.4
1,
083.
4, 529.
1,231.8
1,
2,
3,
537. 8
628. 6
254. 9
449.9
893.
1,
5,
151.
6,
435. 7
1,
11, 000. 7
13, 621. 8
3,
1,
2,
075.
231. 4
544.
638. 1
263. 3
183.
138.
138.
183.
183.
193.
391
Kharasch]
VIII.
2.
35.

ALIPHATIC ACIDS (POLYBASIC SATURATED)

Q=26.05XAr
NumMolec-
Name
ular
weight
ber
of
elec-
trons
(experi-
Kilojoules
mental)
(K.
Kg-cali5
Kg-calis
(calcu-
lated to
the
J.)
Literature
liquid
state)
Malonic acid
(s).
104. 03
Succinic acid (s).
118. 05
Methylmalonic acid
Glutaric acid
118. 05
(s).
Ethylmalonic acid (s)

Dimethylmalonic acid
Tricarballylic acid
132. 06
(s).
132. 06
132. 06
170. 06
(s).
(s)
a-Methylglutaric acid
Ethylsuccinic acid
(s)
384.7
515. 8
527. 5
364.7
154.
154. 9
521.0
9
158. 2
521.0
2,
166. 6
155. 7
159. 5
2, 798.
2, 799. 8
521.0
521.0
2,
521.
806. 5
2,811.9
677.3
677.3
677.3
362.2
365.0
1,
1,
1,
2,
2,
2, 154.
2,
cf. 86;
190.
235; cf. 127,
121, 123.
190.
235; cf. 123,
127.
192.
190.
235;
190.
2,
2,
806. 5
806. 5
146. 08
674.2
2,
821. 5
146. 08
671.5
2,
810. 2
677.3
234.
08
673.0
2,
816. 5
677.3
234.
146. 08
671.4
670.6
2,
809. 8
806. 5
677.3
190.
234.
671.9
2,811.9
677.3
675. 6
676. 1
676.
2,
827. 4
829. 5
829. 5
677. 3
190.
192.
192.
192.
822.3
827.5
827.7
3,
833.6
832. 6
3,
829.9
985.2
983.3
983.4
986.7
3,
146. 08
26
2,
cf.
129.
234; cf. 127.
677.3
190.
190.
127; cf. 192.
190.
235.
190.
190.
234.
190.
(para-acid).
Sym. Dimethylsuccinic acid

(s)
492. 4
494. 5
1,
190.
235;
670.6
671.9
670.6
670.6
146. 08
65. 1
208.4
2,
146. 08
(s)
(s)
82
671. 3
8, 642.
517.7
515.1
516.0
668.6
669.0
146. 08
(s)
251.9
251.5
8,
356.6
357.1
514.7
514.9
514.9
515.7
132. 06
(s)
Methylsuccinic acid
Adipic acid
60.2
60.1
207 2
206.5
90.02
Oxalic acid (s)_..
183.
(anti-acid).

(s) (M. P. 128) (Racemic).
(s) (M. P. 208) (anti).
Unsym.
Dimethylsuccinic
acid
(s).
Methylethylmalonic acid
Propylmalonic acid (s)
Isopropylmalonic acid
Pimelic acid
(s)
(s)
146.
146.
08
82
83
146. 08
146. 08
(s)
(Isopropyl-
160. 04
83
32
succinic acid).
Diethylmalonic acid (s)

Trimethylsuccinic acid
Suberic acid
160. 10
(s)_
174. 11
(s)._
Dimethyladipic
83
160. 10
acid
(s)
174. 11
acid
(s)
174. 11
Diethylsuccinic
acid
(sym.) (M. P. 128).
Diethylsuccinic
acid
(sym.) (M. P. 192).
(s)
174. 11
(s)
174. 11
Ethyl propylmalonic acid
(s)
Tetramethylsuccinic acid
(s)
174. 11
174. 11
2,
2,
2,
4,
441.
463.
463.
484.
473.
123.
4,
115. 1
677.3
4, 115.
4, 129.
190.
187.
235.
192.
234.
190.
187.
235; cf. 127.
182.
4, 120.
234.
3,
3,
9
4
"~~833.~6~
833. 6
989.9
(sym.).
Diethylsuccinic
(unsym.).
C9H16O4
Azelaic acid
188. 13
(s)
4,
84
1,
1,
CgHisO*
Dipropylmalonic acid
(s)._.
188. 13
1,
126. 8
987.8
4, 133.
988. 5
4, 136.
989.4
4, 140.
141.
141. 7
145. 8
4, 775.
4,
4,
778.
795. 2
3.9
192.
234.
1,
146. 2
Tl46.~2
191.
235.
192.
The calculated heats of combustion for compounds in which 2 weakly electronegative groups, such
COOH, are linked together, is given by the expression Q = 26. 05X^+13. The correction factor thus
denotes that the two carbon atoms share a pair of valence electrons in outer energy levels, compared to a
carbon-to-carbon linkage as in ethane.
83 The values
of (192) are on the whole about 0.5 to 0.7 per cent too high.
s^ See footnote
83.
85 See
footnote 83.
82
as
369729
392
Bureau
VIII.
2.
35.
Vol. 2

ALIPHATIC ACIDS (POLYBASIC SATURATED) Continued

Q = 26.05XiV
Number
Molec-
Name
Formula
weight
(experi-
Kilojoules
mental)
(K.
Kg-calis
of
elec-
ular
trons
Kg-cali5
(calculated to
the
liquid
J.)
(N)
C10H18O4
200. 14
50
14
14
16
16
50
50
56
56
Cl 2 2 204.
C12H22O4
C13H24O4
Decanedicarboxylic acid (s) 230.18

Tetraethylsuccinic acid (s) - _ 230.18
Brassylic acid (s) (Undecane- 244. 19
62
62
68
C19H36O4
Cetylmalonic acid
Heptylmalonic acid
C10H18O4
C10H18O4
C11H20O4
C11H20O4
200.
200.
216.
216.
(s)
Triethylsuccinic acid (s)

tt-Octylmalonic acid (s)
Nonanedicarboxylic acid
(s)
Literature
state)
/ 1,296.4
I 1,297.3
5,425.4
5,429.2
4
3
5,
450. 5
445. 9
1,302.5
5,
6,
102. 1
1,
6,
091. 7
1,
6,
740. 8
6, 774. 6
7, 401. 6
1,
1,
610. 7
618. 8
768. 6
2,
707. 3
11,330.0
1,
1,
85 1,
1,
1,
1,
302.
301.
458.
455.
1,
302. 5
191.
235; cf. 127.
302. 5
458. 8
458. 8
192.
234.
192.
235.
1,
615.
615.
771. 4
235.
235.
235.
2,
709. 2
192.
691.7
536.1
175.8
136.7
130.
130.
1,
1,
dicarboxylic acid).
328.29
(s)
k See footnote
104
83.
See footnote
83.
HYDROXY POLYBASIC ACIDS (SATURATED)
36.
Q=26.05Xi\r+6.5k+6.5v
C3H4O5C3H4O6-
Tartronic acid (s)

Mesoxalic acid (s)(Dihydrox-
ymalonic
C4H6O5-
C4H 6
Z-Malic acid (s)

d-Tartaric acid
6.
C4H6O6-
(s)
Z-Tartaric acid
mic; anhydr.).
d, ^-Tartaric acid
mic; cryst.).
d,
C4H6O6-
(s)
(Race-
(s)
(Race-
C4H6O6CsHgO-.
Mesotartaric acid (s) S7

Trihydroxyglutaric acid
CeHioOsCeHioOs-
Mucic
acid
Citric acid
Citric acid
C6H 8 07.H 2 0.
CsHuOe
(s).
(s)
Allomucic acid
CfsHsO?
(s)
136. 03
165.4
128.2
134. 05
150. 05
12
10
320.1
275.1
1,
1,
339. 6
151. 29
325.6
286.5
75.
54; cf.
10
278.
273.
1,
164. 3
286.5
145.85a
|l50. 05
1,
150. 05
10
277.8
1,
142. 5
161. 8
150. 05
180. 06
10
14
276.0
388.3
1,
210. 08
210. 08
18
18
483.6
494.2
2,
474.5
471.4
889.0
(s)
(anhydr.)
192.06
(s)
(cryst.)
210. 08
18
18
205.11
34
Dimethyldihydroxyadipic
acid
120. 03
acid).
54.
""286.Y
155. 1
623. 9
286.5
397.2
2,
023. 9
066. 7
507.9
1,
985. 8
488.4
1,
717. 8
145.
1S3.
1,971.4
3,
898.7
191; cf. 127.

127.
243.
(s)
Little value should be attached to the work of this investigator. The results are probably not better
1 to 2 per cent and are too high.
(54) give also the heat of combustion of various ammonium and substituted ammonium
salts of d-tartaric, racemic and mesotartaric acids:
56a
than
87
The authors
Kg-cahs
3.
Ammonium
Ammonium
Ammnninm
4.
Methylammonium
1.
2.
trate5.
6.
d-bitartrate
biracemate
himesntartratft
Ethylammonium
341.7
339.5
341.2
1,
1,
430.
420. 8
427. 9
508.0
2,
126.
506.0
2,117.6'
665.4
2,
1,
d-bitar-
Methylammonium
K.J.
Kg-calu
7.
8.
9.
birace-
11.
784. 7
Phenylammonium
Benzylammonium
Benzylammonium
tartrate
663.
2,
775.
.4,516.9
1,
079. 3
1,
077. 3
4, 508.
1,
229. 9
5,
147.
1,
231. 5
5,
153.8
birace-
mate
10.
d-bitar-
Ethylammonium biracemate .d-bitarPhenylammonium
K.J.
birace-
bimeso-
393
Kharasch]

VIII.
2.
37.
POLYBASIC ALIPHATIC ACIDS (UNSATURATED)

Q=26.05XiVr+13y+16.5x
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
(experi-
Kilojoules
mental)
(K.
Kg-cali5
of
elec-
trons
(calcu-
lated to
J.)
(N)
Fumaric acid
C4H4O4
(s) 88
(trans)
. .
C4H4O4
C5H6O4
Itaconic acid (s) (Methylenesuccinic acid).
C5H6O4-
116. 03
12
320.0
1,
339. 2
325.6
116. 03
12
326.1
1,
364. 7
329.1
130. 05
18
475.
475.
1,
990. 4
987. 9
481.9
479.
478.
476.
475.
2,
006.
003.
995.
991.
988.
2
8
8
6
485.4
481.9
183.
151; cf. 127.
183.
151; cf. 127.
183; cf. 127.
796.1
631.
2, 632.
2, 669.
3, 331.
638.2
638.2
638.2
794.5
183.
183.
192.
145.
305.9
1,
Citraeonic acid (s) (methyl}l30. 05

maleic acid) (cis)
Mesaconic acid (s) (Methyl-
18
/
\
18
CoH60c
174. 05
18
475.1
C 6 H 8 04
C H 8 04
C H 8 04
a,/3-Hydromuconic ac'd (s)._ 144.06

/S,7-Hydromuconic acid (s)._ 144. 06
144.06
Allylmalonic acid (s)
158. 08
Teraconic acid (s) (7-Dimethylitaconic acid)
24
24
24
30
628.8
629.1
Acetylenedicarboxylic
10
fumaric acid)
C7H10O4
C4H2O4
(trans).
acid
Literature
state)
}l30. 05
C5H6O4
the
liquid
114. 02
637. 8
1,
2,
1,
1,
1,
2,
~~"48L9~
8
2
7
280. 2
190; cf.
127,
190; cf.
151.
183.
151; cf.
163,
146.
127,
127.
183.
(s).
88
collection of the heats of combustion of some stereo isomeric acids is given
p. 90; 1892.
81 The values of
(192) are from 0.5 to 0.7 per cent too high.
38.
by Liebermann,
Ber., 25,
AROMATIC ACIDS
Q=26.05Xivr-3.5a-6.5b
C7HGO2-
Benzoic acid
(s) eo .
122. 05
90
30
771. 2
3,
778.0
227. 5
63; cf.
153,
221,
241,
85,
216,
71,
213,
220,
214.
189.
C 8H 8
2.
C 8H 8
C
C
8
8
C9
H
H
H
o-Toluic acid
136. 08
(s)_.
2_
r/i-Toluic acid (s).
136. 08
2-
2>-Toluic acid
3.
o-Oxymethylbenzoic acid
36
34
164.06
164.06
38
38
(s)
164.06
150. 08
(p-Isopro-
164. 10
38
42
48
o-Acetylbenzoie acid
w-Acetylbenzoic acid
CgHsOs.-
p-Acetylbenzoic acid
Mesitylenic acid (s)
H
H
Cuminic acid
(s)
36
136. 08
152. 06
(s)
CqHsOs.
C9H10O2-.
C10H12O2.
36
(s).
(s)
(s)
928.
921.
3,
928.6
3,
922.
3,863.1
926.9
887.3
3,
3,
3,
930.8
887. 5
858.
886. 2
/
\
191,
80,
227,
67,
84,
228,
159,
219,
218,
5.
930.8
189.
5.
930.8
891.7
879.
713. 4
151.
151.
1,
1,
084. 7
238.
4, 539.
1,
5,
181. 5
1,
231.
227. 6
5,
155.
137. 5
1,
083. 6
243. 4
151.
189.
189; cf. 30.
pyibenzoic acid).
8
2_
a-Naphthoic acid
(s)
172. 06
2.
/S-Naphthoic acid
(s)
172. 06
48
48
1,
1,
5,
1,
233. 9
233. 9
190.
00 The
above value is the one accepted at the third conference of the International Union of Pure and
Applied Chemistry, held at Lyons, 1923. It' is the value found by Dickinson, Bull. Bur. Stds., 11, p. 189;
1915.
See also discussion of Verkade in Chem. Weekblad, 19, p, 389; 1922,
394
Vol. g

VIII.
2.
HYDROXY AROMATIC ACIDS
39.
Q=26.05XN+3.5m-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
Kg-cahs
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
J.)
(N)
Salicylic acid (s)
138. 05
28
m-Hydroxybenzoic acid
C7H6O3--
C7H6O4
(s)._
2>-Hydroxybenzoic acid
acid
/3-Resorcylic
(s)
138. 05
28
026. 2
028. 3
041. 2
032.
729.4
230.
217.
198.
89; cf.62,189.
038.
032.
035.
3, 029.
2, 831.
7
9
729.4
3,
3,
729.4
199.
89; cf. 189.
189.
680.8
189.
650.
652.
362.
3, 743.
3, 694.
632.2
632.2
189.
189.
163.
189.
199.
199.
723.
3,
723.6
3,
726.
3,
723.8
3,
726.
3,
724.7
725.
723.
C7H6O3-
Literature
state)
C7H6O3
the
liquid
(s) _ _
138. 05
28
(2,4-
154. 05
26
676.5
24
633.4
633.7
803.5
894.6
882.8
878.7
89.
Dihydroxybenzoic acid).
C7H6O5
C7H6O5-
C H 6 04
C 8 H 03
C 8 H 8 03
C 8H 3
8
C
C
8
8
H
H
03
C10H10O5
C10H10O6
81
As
Pyrogallolcarboxylic acid (s)

Gallic acid (s) .
. .
Piperonylic acid (si
p-Methoxybenzoic acid (s) . _
1,6,2-Hydroxytoluic acid (s)^
1,2,3-Hydroxytoluic acid (s).
170.
1,2,5-Hydroxytoluic acid
1,2,4-Hydroxytoluic acid
Opianic acid (s)
(s).
(s)_
152. 06
152. 06
210. 08
170.
05
05
166. 05
152.06
152.06
152.06
226. 08
24
30
34
34
34
34
34
40
38
1,
1,
2,
2,
3,
3,
677. 4
879.5
877.8
3,
680. 7
673. 6
089. 7
025.
4, 557. 1
3,
4, 286.
901.7
882.2
882.2
9
5
a result of a very exhaustive and painstaking investigation, these authors
1,
882.2
882.2
199.
090. 5
106' Cf. 107.

107.
1,021.9
199
recommend the use
cf
salicylic acid as a secondary thsrmochemical standard.

Compare Verkade and Coops, Bull. soc. chim., 37,
p. 1536, 1925; Verkade and Coops, J. Chem. Soc, p. 1437, 1926; and particularly Cohen, Verkade, Miyaki,
Coops and van der Hoeve, Verslag Akad. Wetenschappen Amsterdam, 35, p. 48; 1926.
82 The values of these authors have been corrected to the 15 calorie.
8 3 The numbers denote the positions of carboxyl, hydroxyl and methyl groups, respectively.
PHENYLATED ALIPHATIC ACIDS
40.
Q=26.05XiV-3.5a-6.5b
Phenylacetic acid
CgHsOs-
Mandelic acid
CsH 8
(s)
(s)
CoH0 2
Phenoxyacetic acid (s)

Phenylpropiolic acid (s)
CoH 8
Cinnamic acid
3-
02-
CoH 8
{trans)
Allocinnamic acid
36
152.06
152.06
146. 05
148. 06
34
34
38
40
84
930. 2
3,
892.
934.3
890.3
902.8
3, 725.
895.2
911.7
1,
021. 1
040. 2
778. 2
4, 270. 2
4, 357. 4
1,
3,
1,
016. 5
048.
1,
052.
1,
045.
1,
208; cf. 66.

241,
5,
106.
199; cf. 182.
148.06
40
1,
047.
4, 385.
(s)
148. 06
164.06
1,044.4
991.4
4, 370.
p-Hydroxycinnamic acid (s)

(trans) (M. P. 206).
Allo-p- h y dr xy cinnamio
acid (s) (cis) (M. P. 126 to
40
38
999.9
177; cf. 183,

108.
183; cf. 145.
177.
164.06
38
996.5
4, 174.
1,
003. 4
177.
(/3-
150. 08
42
1,
085.
4, 540.
1,
090.
189.
(s)
192.06
40
1,
067. 5
4,
192.06
40
1,
076. 5
4, 509.
08
46
1,
195.
5,
002. 8
1,
208.
08
162. 08
46
46
1,
198. 4
197.
5,
020. 1
014. 2
1,
204. 8
204. 8
(M.
CoHgCV
C H
(s)
136. 05
(cis)
(s)
P. 58).
Atropic acid
4, 152.
127).
C9HJ0Q2-
Hydrocinnamic acid
(s)
phenylpropionic acid).
CjoHsO*.,
Piperonylacrylic
acid
(trans) (M. P. 238).
CioHgOtCioHioO?.
Allopiperonyl acrylic acid (s).

(cis) (M. P. 99 to 100).
PhenylisQcrotoniq acid (s) 86
CioH,o0 2 -
a-Methylcinnamic acid
(s) _
C10H10O2.
/S-Methylcinnamic acid
(s)_.
162.
471. 8
(cis),
162.
1,
5,
1,
163.
163.
most peculiar that these authors obtained 1,042.8 kg-cahs for this acid while for naphthalene,
which was used in standardizing the bomb, their value is 0.9 per cent higher than the accepted value.
85 One of these authors showed later (Ber., 35, p. 2908, 1902), that cinnamic acid upon illumination goes
over to a a-truxillio acid. However, upon combustion there was no evidence of any energy difference.
84
It is
See also Ber.,
28, p. 1443; 1895; 46, p. 267; 1913.
W C 6 H.CH:CH.CH2COOH,
Kharasdi]
VIII.
2.
40.
395
PHENYLATED ALIPHATIC ACIDS Continued

Q=26.05XiV-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
Kg-calis
(calcu-
Kilo-
Kg-calis
(experi-
joules
mental)
(K.
lated to
J.)
C10H10O3
Methylcoumaric acid (s)

(trans) (M. P. 182 to 183).
Methylcoumarinic acid (s)
(cis) (M. P. 91 to 92).
p-Methoxy cinnamic acid
C10H10O3
Aho-p-methoxycinnamic
C11H10O2
Cinnamylideneacetic
C10H10O3
(s)
(trans)
(M. P.
(M.P.66
Allocinnamylideneacetic acid
Acetylcoumaric
C11H10O4
CnHioOi
C11H12O3
CiiHuOs
CuHuOs
C12H14O3
C, 2 Hi20 3
C12H12O3
Ethylcoumarinic acid (s) (cis)

(M. P. 101 to 102).
acid
Propylcoumaric
(s)
(trans) (M. P. 105 to 106).
Propylcoumarinic acid (s)
(cis) (M. P. 83 to 84).
/3-BenzaUevulinic acid (s)
5-Benzahevulinie acid (s)
C,3H I6 03
r<-Butylcoumaric
C13H16O3
rc-Butylcoumarinic acid
C14H18O3
CnHisOs
acid
(M. P. 89
CHH12O2
Diphenylacetic acid
C14H12O3
C16H16O2
C17H16O3
Benzilic acid
C 17 Hi 6 03
(s)
to 90)
863.
1,
152. 5
177.
4,
889. 4
1,
156.
177.
170.
08
44
1,
163.
4,
871. 8
1,
172. 2
177.
170.08
44
1,
172. 2
4,
910.
1,
175. 7
177.
174. 08
50
1,
310. 6
5,
480.
1,
322.
155.
517. 7
1,
325. 5
155.
177.
08
50
1,
319. 4
5,
206.08
46
1,
207. 6
5, 058. 6
1,
217.
208. 08
46
1,
211. 7
5, 075. 8
1,
221. 3
177.
206. 08
192. 10
46
50
1,
195. 5
316. 5
5,
003. 2
514. 8
1,
1,
204. 8
328. 8
183.
177.
174.
._
(s)
(s)
_
Dibenzylacetic acid
1,
5,
192. 10
50
1,
323.
5,542.0
1,
332.
177.
206. 11
56
1,
470. 4
6, 159. 5
1,
484. 8
177.
206. 11
56
1,
476. 3
6,
184. 2
1,
488. 3
177.
204. 10
54
54
1,
5,
915.
5, 901. 3
1,
1,
413. 4
410.
1,
419. 7
419. 7
182.
182.
1,
220. 13
62
1,
630. 6
6, 830.
641.
177.
220.13
62
1,
637.
6,
857. 4
1,644.6
177.
234. 14
68
1,
789. 7
7,
497.
1,
797. 4
177.
234.14
68
1,
791. 3
7,
503.
1,
800. 9
177.
212. 10
64
1,
651. 5
6,911.5
1,
654. 2
182;
228. 10
240. 13
268. 13
62
76
78
618. 2
1, 954. 3
2, 035. 2
772. 2
8, 178. 8
8, 525. 5
1,
182.
2,
612.
972. 8
047. 9
227.
151.
268. 13
78
2,
2,
047.
151.
(s)
(s)
/3-Tolylmethoxycinnamic
6,
1,
1,
cf.
227.
(stable).
(s)
/3-Tolylmethoxycinnamic
acid
4,
167.
204. 10
(cm) (M. P. 53 to 54).

Isoamylcoumaric acid (s)
(trans.) (M. P. 79 to 79.5).
Isoamylcoumarinic acid (s)
(cis) (M. P. 80 to 80.5).
acid
161.
1,
138).
acid
(s)
(trans) (M. P. 154 to 155).
Acetylcoumarinic acid (s)
(cis) (M. P. 85).
Phenylparaeonic acid (s)
Ethylcoumaric
acid
(s)
(trans) (M. P. 133 to 134).
(trans.)
1,
44
165).
CiiHio0 4
(M. P.
44
08
).
acid
CnH,o02
(s)
170. 08
170.
87
acid(s) (cm)
(s)
Literature
state)
(A")
C10H10O3
the
liquid
039. 2
8, 542.
(labile).
(s)
M. P. 170 (liq- cryst.) clears at 185.

ts
The work of these investigators is not quite reliable. Thus, the value of standard naphthalene used
in the calibration of the bomb is about 0.9 per cent too high, and yet their value for cinnamic acid is within
0.1 per cent of the best value.
41.
97
POLYBASIC AROMATIC ACIDS

Q=26.05XA"-3.5a-6.5b
Phtbalic acid
(s)
Isophthalic acid (s)_.

Terephthalic acid (s)
Trimesic acid (s)
Uvitic acid (s)
Pyromellitic acid
Naphthalic acid
(s)
(s)
(1,8-
166. 05
30
771.0
3, 226.
774.5
166. 05
166. 05
210. 05
188.06
30
30
30
36
768.3
770.4
767.0
928.3
215. 3
3, 224.
3, 209. 9
3, 884. 9
774.5
774.5
771.0
927.3
189; cf. 183,

127.
189.
189.
189.
189.
254.05
216. 05
30
48
776.8
1,244.1
3,
5,
250.
202. 8
767.5
230. 4
127.
342. 05
30
787.5
3,
295. 7
760.5
189.
3,
1,
Naphthalenedicarboxylie
acid).
MeUitic acid
89
1
The combustion
Boe footnote 99.
(s)
of these acids
was rather
unsatisfactory.
Consult original paper.
Bureau
396
Vol. %

VIII.
2.
42.
PHENYLATED POLYBASIC ALIPHATIC ACIDS

Q=26.05XiV-3.5a-6.5b
Number
Molec-
Name
Formula
ular
weight
(experi-
Kilojoules
mental)
(K.
Kg-calis
of
elec-
trons
Kg-calis
(calcu-
lated to
J.)
Benzalmalonic acid
Benzylmalonic acid
C10H10O4
O10H10O4
C12H10O4
Phenylsuccinic acid
(s)
(s)
(s)
Cmnamylidenemalonic acid
192. 06
194.08
194. 08
218. 08
40
42
42
50
70
Literature
state)
(JV)
C !0 H O4
the
liquid
056.
082. 5
082. 3
319. 4
4,
1,
810.
806. 6
1,
1,
1,
2 1,
419.
1,
048. 5
090. 6
090. 6
322.
183.
192.
234.
155.
576.
1,
816.
182; cf. 145.
560. 3
1,
816.
182; cf. 145.
2
034. 6
2,
080.
155.
155.
1,
3
4
1,
5,
517. 7
7,
7,
4, 530.
4, 529.
1,
(yellow).
(s)
C16H14O4
a-Diphenylsuccinic acid
(s)
270.11
CieHuOi
(anhydr.)
(easily
sol.
form). 3
/S-Diphenylsuccinic acid (s)
270. 11
70
1,
PisHieCU
(difficultly sol.).
/T-Trnxillic acid (s)
296.13
80
Cinnamylidenemalonic
436. 16
083. 5
2, 638. 6
8, 713.
2,
11,
acid 5 (exposed to the action of light).
See footnote 95.
The heat
in acetone)
4
is
combustion of the acetone addition product of a-diphenylsuccinic acid (easily soluble form
given as 2,237.9 kg-calis.
(234) report the heats of combustion of diphenylsuccinic acid (racem.) and diphenylsuccinic
of
The authors
acid (anti) as 1,807.7 kg-cali5

*
and
1,809.0 kg-calu, respectively.
Thestructure suggested for this polymer is
C H .CH.CH.CH:C:(C02H)2
6
(H0 2 C)2:C:CH.CH.CH.C 6 H 5
I
HYDROAROMATIC AND POLYMETHYLENE ACIDS
43.
Q=26.05XiV+13z+13aa
C4H6O2-
Trimethylenecarboxylic acid
(Cyclopropanecarboxylic
acid).
86.05
18 /
I
479.
2, 007.
483.7
2,
022.
481.9
175.
215.
481.9
187.
C5H6O4-
,o:-Trimethyle n e d i c a rboxylic acid (s) (1,1-Cyclo-
C5H0O4-
propanedicarboxylic acid).
a,j8-Trimethyle nedicarboxylicacid (s) (ds-l,2-Cy-
130. 05
18
482.9
2,
020.
130. 05
18
483.9
2,
025.
481.9
187.
641.0
639.2
2,
685. 2
673.
638.2
2,
175.
215.
clopropanedicar boxy lie

acid).
C5H8O2-
Tetramethylenecarboxylic
acid (Cycl obutanecar-
CeH
04-
06
24 /
a,a-Tetramethyienedicarboxylic acid
1 100.
boxylic acid)
144.05
24
642.0
2,686.8
638.2
187.
144. 05
24
642.1
2,
687.
638.2
187.
144.05
24
639.4
2,673.9
638.2
243.
128.10
36
934.0
3, 905.
937.8
215.
192. 10
28
833.3
3,
484.
755.4
43.
885.7
3,
710. 2
892.2
165.
167.
(1,1-Cyelo-
(s)
butanedicarboxylic acid)
8
04-
a,/S-Tetramethylenedicarboxylic acid
(s)
(cis-1,2-
Cyclobutanedicar boxy lie

acid).
04-
0,7-Tetramethylenedicar-
C7H12O2-
Cyclohexanecarboxylic acid
(Hexahydrobenzoic acid)
boxylic acid
(M.
C Hi
7
8-
(s).
P. 28).
Hexahydrotetrahydroxybenzoic acid
(s)
(Quinic
acid).
C7H10O2-
Ao-Tetrahydrobenzoie
C7H10O2-
Ai-Tetrahydrobenzoic
acid
08
34
126. 08
34
856.7
3,586.2
892.2
08
30
781.5
3, 245.
775.6
187.
218.05
218.
05
18
482.7
2,020.1
2, 020.
481.9
187.
126.
(s).
acid
(s).
C7H10O4-
a,0-Pentametnylenedicarboxylic acid
(s)
158.
{trans-1,2-
Cyclopentanedicarboxylic
acid)
CrHeOs
a,a,/9,/3-Trimethylenetetracarboxylic acid (s) (1,1,2,2-
Cyclopropanetetracarboxylic acid).
6
The
value for this
compound appears
to be entirely too large
and would certainly bear reinvestigation.
Kharasch]
VIII.
2.
43.
397

HYDROAROMATIC AND POLYMETHYLENE ACIDS Continued

Q=26.05X-ZV+13z+13aa
NumMolec-
Name
Formula
ular
weight
Kg-cali 5
ber
(experi-
Kilojoules
mental)
(K.
Kg-calis
of
elec-
trons
(calcu-
lated to
the
.)
(N)
C 8 H 8 04
Ai,4-Dihydroterephthalic
04
Ai,5-Dihydroterephthalic
CH
04
A2,5-Dihydroterephthalic
acid
acid
acid
A2-Tetrahydroterephthalic
Ai-Tetrahydroterephthalic
835.6
3, 497.
842.1
3,
06
32
844.9
3, 535.
168. 06
170. 08
32
34
842.6
881.1
3,
524. 2
846.6
185.
846.6
185.
168.
(s)_
846.6
186.
526. 3
3, 687. 4
846.6
892.2
186.
186.
892.2
185.
(s).
882.3
3,
692. 4
042.
4,
364. 9
1,
055.
167.
40
1,044.8
4,
376. 7
1,
048. 5
187.
172. 10
36
929.1
3,
888.
937.8
185.
172. 10
36
928.2
3,
884.
937.8
185.
172. 10
36
930.4
3,
893. 7
937.8
79.
490. 08
087. 9
2,
4,
052. 5
549. 6
1,
094.
106.
215.
542. 5
1,
094.
215.
215.
170. 08
34
140. 10
40
1,
140.10
(s).
Cyclohexylideneacetic
32
32
(Jum.).
C 8 Hio04
C 8 Hi20
168.06
168.06
(s).
(s)
Dihydroterephthalic acid
acid
state)
(s).
C 8 H 8 04
C 8 Hio04
acid
Literature
liquid
acid
(s). 7
C Hi
8
Cyclohexene-1-aceticacid
02
(s)_
C 8 Hi 2 04
Hexahydroterephthahc acid
C Hi
Hexahydroterephthalic acid
C Hi
04
(s) (trans).
8
(s) (cis).
8
1-2-C y clohexanedicarboxy lie

acid
(s)
(trans).
C7H4O7.3H2O.-
Meconic acid
C Hi40
Cycloheptanecarboxylic acid
254. 08
(s)
142.11
""42"
1,
(s).
C Hh0 2
Hexahydro-m-toluic acid (s)

(3-Methylhexamethylene-
C Hi40 2
carboxylic acid)
Cyclooctanecarboxylic
C9H14O2
a-Cyclohexene-1-propionic
C10H16O2
C10H16O2
Isocampholytic acid
acid
'
142. 11
42
1,
086. 2
4,
142. 11
42
1,
089. 2
4, 555.
1,
094.
154.11
46
1,
199. 6
5,
025.
1,
204.
167.
168. 13
168. 13
52
52
1,
700.
5, 711.
1,
1,
367. 6
367. 6
44.
1,
363.
365. 7
175.
(act).
acid.
Campholenic acid
(s)
(M. P.
(s)
5,
44.
60).
CioHieOs
a-Tanacetoneketocar boxy lie
C10H16O4--
d-Camphoric acid
CioHi 8 02
CioHisOa
C 12 Hl20l2
Campholic acid (s) _

Hexahydrocumic acid
acid
184. 13
50
1,
327.
5,
1,
322.
200.13
48
8 1,
243. 8
5, 205. 3
1,
250. 4
170. 14
170. 14
54
54
36
1,
412.
396. 4
5,
1.
923.2
3,
904. 9
839. 7
863. 6
406. 7
406. 7
937. 8
560. 5
(s).
(s)
(s)
Hexahydromellitic acid
(s)
348. 10
1,
5,
1,
187; cf. 124,

127, 112.
44.
243.
186.
(Jum).
CeHio CH.COOH.
Values of (124), (127), and (112) vary between 1,242.5 and 1,254.2 kg-calis.
This value has been corrected according to the method employed by Swietoslawski, J. Amer. Chem.
Soc, 42, p. 1093; 1920. The correction factor employed by him appears to be too large, however.
7
44.
ACID ANHYDRIDES
Q=26.05XiV+10bb
C4H2O3-
Maleic anhydride
C4H4O3-
Succinic anhydride
C4H6O3C5H4O3CsEUOsC5H6O3-
(s)...
(s)_.
Acetic anhydride (v)__.

Acetic anhydride (liq.)
Itaconic anhydride
Glutaric anhydride
(s)
(s)
Monomethylsuccinic anhydride
(s).
98.02
100.03
102.00
112. 03
114. 05
114.05
333. 9
1,
369.4
369.6
458.3
431.9
1,
339.1
374.3
1,
4
9
8
6
2
481.5
528.0
527.7
2, 015.
2, 209. 7
2, 208.
491.9
531.0
531.0
1,
1,
397.
545.
546.
916.
806.
182.
182.
234; cf. 127.

[223.
183.
183.
234.
398
Bureau
Vol. 2
VIII.
2.
44.
ACID ANHYDRIDES Continued

Q=26.05XiV+10bb
NumMolec-
Name
Formula
ular
weight
ber
of
Kg-cal
Kg-cal
elec-
trons
(experi-
Kilojoules
mental)
(K.
15
15
(calcu-
lated to
J.)
the
Literature
liquid
state)
CeHgOs-
Dimethylsuccinic anhydride
C6H 8
128.06
26
682.6
2,
856.
687.3
234.
128.06
26
679.3
2,
842.
687.3
234.
128.06
26
681.1
2,
850.
687.3
234.
128.06
26
684.8
2,
865.
687.3
234.
130. 08
142. 08
28
32
746.6
836.1
3, 122.
739.4
843.6
118.
234.
148. 03
30
783.
780.
3, 278.
784.5
08
36
4
3,900.4
947.8
189, 217; cf.

127.
172.
937.8
3,
anhy-
156.09
38
992.6
4, 154.
999.
234.
anhydride
156.09
38
998.3
4,177.9
999.9
234.
anhydride
156.09
38
995.6
4, 166.
999.9
234.
997.2
4, 173.
176.06
10 1,
094.
251.
4, 578.
182. 11
42
48
238.
1,
260.
184. 12
50
1,
309.
5,480.3
1,
312. 5
234.
183; cf. 127,
124.
234.
Naphthalic anhydride (s)

198. 05
Tetraethylsuccinic anhydride 212. 15
48
62
11 1,
257.
621. 3
5,
259.
785.
1,
6,
240. 4
625.
127.
234.
214. 18
226. 08
64
60
1,
669.
555.
6,
677. 2
566.
205;
242. 21
252. 10
76
70
1,
985. 5
815.
1,
989. 8
826. 5
227.
234.
250. 08
68
1,768.9
7,
402.
1,
774. 9
182.
298. 11
406. 18
80
128
091.
3, 308.
8, 745.
2,
107.
13, 834.
3,
337. 4
227.
227.
462.24
152
3,931.4
16, 441.
3,
962. 6
227.
(s)
H
CH
C
(unsym.).
(sym.)
(M. P.
87).
03--
03--
Monoethylsuccinic
(M. P.
43).
anhy-
dride.
C6H10O3
C7H10O3
.
Propionic anhydride
.
Trimethylsuccinic anhydride
3,
499.
(s).
C8H4O3
Phthalic anhydride
CgHioOs
Hexahydrophthalic
C8H12O3-
Hexahydrophthalic
dride
dride
(s)
anhy-
(s)
anhy-
C8H12O3
Diethylsuccinic
(s) (unsym.).
Diethylsuccinic
Hi 2
(s)
3, 266.
172.
924.
(s).
(racem.) (sym.).
Diethylsuccinic
(s)
932.0
(sol.) (trans.).
Tetramethylsuccinic
(s) (sol.) (cis).
CsHmOs
dride
154.
anhydride
234.
(racem.) (anti).
C10H8O3
Phenylsuccinic anhydride
C10H14O3
Camphoric anhydride
C10H16O3
Triethylsuccinic
(s)
(s)
anhydride
1,
5,
2, 106.
(s).
C12H6O3
C12H20O3
1,
1,
(s).
C12H22O3
C14H10O3
Diethylacetic anhydride (s)._
C14H26O3
Ci 6 12 3
Heptylic anhydride (s)

Diphenylsuccinic anhydride
C16H10O3
Diphenylmaleic
C18H14O3
C28H22O3
Cinnamic anhydride
Diphenylacetic
C32H30O3--
Dibenzylacetic anhydride
Benzoic anhydride
(racem.)
(s)
1,
1,
980. 2
1,
6, 508. 1
1,
8, 303.
1,
7, 599.
227.
cf.
227.
(s).
anhydride
(s).
(s)
anhydride
2,
(s).
(s)
(glassy).
The mean
of several values.
h Individual determinations do not agree better than 0.7 per cent; values of (127) are also on the whole
per cent higher than those of (183).
399
Kharasch)
VIII.
2.

45.
LACTONES
Q=26.05XAr+13
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
Kg-calu
of
elec-
trons
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
J.)
the
Literature
liquid
state)
CeHôOs
C6H10O6
Saccharinic acid lactone
(s) 12 -
C6HioOed-Mannolactone
C6H10O6
C7H10O4
12
(s)
Terebic acid (s) (7,7-Dimethylparaconic acid)

Glucoheptonic acid lactone
07
162. 08
178. 08
178. 08
178.
158.
08
08
24
22
22
22
30
656.6
614.7
616.3
618.7
778.3
747.
2, 570.
2, 577.
2, 587.
3, 254.
2,
4
4
9
662.2
625.1
625.1
625.1
794.5
195.
68.
68.
68.
145.
208. 10
26
726.3
3,
037.
735.8
68.
134. 05
238. 11
884.1
836.7
1,
136. 7
699. 9
3, 499.
4, 753. 7
891.7
843.5
194. 08
34
30
42
1,
139.
199; cf. 157.

68.
106; cf. 107.
224. 10
46
13 1,
262. 9
5,
281. 5
1,
139.
106.
381.2
223; cf. 40.

26.
223.
78.
(s).
C H 6 02
CsHuOg
CjoHjoO*
Phthalide (s)
Glucooctonolactone (s)
Meeonine ( D imethoxy-
CnHi 2 05
Methyl opianate
3,
phthalide).
(s)
12
c
CH C CH
3
CH
CH2OH.
A A
H H
H OCH3
13
/ \
o
OCH3
46.
METHYL ESTERS OF MONOBASIC ACIDS

(^=26.05X^+16.5
C H,o0 2 C 6 H,o02.
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
C9H14O2-
Methyl
CCH14O2C10H16O2-
Methyl
C2H4O2-
C Hg0 2
3
C4H8O2-.
C 4H
03..
C5H10O2-
C 5 Hjo0 2 .
C5H8O3-.
6
formate (v) . formate (liq.).

acetate (v) . .
acetate
(liq.)
propionate (v)
60
60.03
74
74.05
88
104. 08
18
butyrate
isobutyrate
102
26
26
acetylacetate
381.
20
lactate
102. 08
116. 06
114. 08
240.2
233.1
397.7
390.0
-"l4"
552.3
497.2
692.8
694.2
594.0
804.4
1,004.5
974.8
663.
1, 631.
1, 595.
2, 309.
2, 079.
2, 897.
1,
172; cf. 65.

223.
2,904.5
537.5
498.3
693.8
693.8
810.8
810.8
163.
215.
7
3
3
75.
65.
154.
114. 08
30
809.
484.
369. 6
3, 383. 7
cyclohexene-1-ace-
154.11
46
1,
210.
5,
069.
1,
221. 3
167.
Methyl cyclohexylideneace-
154.11
46
1,
216. 5
5,
095. 9
1,
221. 3
167.
168.13
52
1,349.3
5,
652. 2
168.13
52
1,
373.
5,
755. 3
1,
377.
167.
dimethylacrylate
cyclobutanecarbox-
""16"
78.
2,
3,
ylate.
tate.is
tate.
C10H16O2-
C10H16O2C10H16O2-
CiiH 18
u
3.
Not e
a-cyclohexene-1propionate.
Methyl
methyl-4-cyclo-
hexylidene-1-acetate. 16
methyl-4-cyclohexene-1-acetate.
Methyl a-cyclohexylidenepropionate.
Methyl pinonate.
Methyl
52
1,
362.
5, 705.
52
1,
374. 6
5,
198. 14
56
1,
477. 3
6, 188.
1,
377. 6
167.
758. 2
1,
377.
167.
1,
481. 8
175.
corre ction for cyclobutane ring in formula for polymethylenecarboxylic acids.
H
M)CH
/Vc-c(
CH
168.13
168. 13
167. 5.
!H 2 C^
OCH3
400
Bureau
VIII.
2.
47.
[Vol.2

METHYL ESTERS OF MONOBASIC AROMATIC ACIDS

Q=26.05XiVr+16.5-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
ber
trons
Kg-calis
(calcu-
Kilo-
Kg-calis
of
elec-
(experi-
joules
mental)
(K.
lated to
the
J.)
Literature
liquid
state)
CHg0 2
152. 06
36
34
34
943.5
898.3
895.4
3,
184.06
166.08
30
40
801.6
3,
136. 06
152.06
CsHsOs
CsHgOs
Methyl p-hydroxybenzoate
CsHsOs
Methyl
Methyl
948. 6
759. 4
747. 3
950.8
902.2
902.2
205
206
354. 7
4, 472. 5
805.0
191.
191.
3,
3,
191.
(s).
C9H10O3
Methyl
Methyl
Methyl
Methyl
CioH 10 02
C10IISO2
Ci2H,o0 2
C12H14O3
gallate
(s) - .
anisate (s)_.
cirmamate
(s)
ethylcoumarate
068. 7
1,
213.
210. 4
5,
196. 2
1, 401. 5
1, 490. 3
5,
162.08
46
160.06
186.08
206.11
44
54
56
1,
206.11
56
1,
phenylpropiolate
/3-naphthoate (s)
1,
1,
076.
070.
002.
5, 865.
6, 242.
5,
4
4
5
3
"
1,
074. 5
1,
221.
I,"
189."
406. 7
501. 3
191.
163.
138.
191.
177.
1,504.8
177.
1,
1,
3"
(trans)
Methyl
C12H14O3
ethylcoumarinate
495.
6,
262. 6
(cis).
48.
METHYL ESTERS OF POLYBASIC ALIPHATIC ACIDS

Q = 26.05 XiV+16.5dd
Dimethyl carbonate
Dimethyl oxalate (s)
C3H603
C4H 6 04
CsH
C H
CcH
6
S
8
90.05
118.05
14.
340.8
7,
1,
401.
401.
552.
2,
554.3
2,
664.3
669.2
2,
132.06
04
Dimeth yl fumarate
04
04
C6H10O4
12
Dimethyl maleate
(s)
(s)
20
144.06
144.06
24
24
146.00
26
CeHioOe
/
I
Dimethyl succinate
(s)
Dimethyl racemate
(s)
178.
08
22
d-Dimethyl
CeHioOe
Dimethyl mesotartrate
C7H10O4
C7H10O5
C7H12O4
C8H12O4
2,
708.
707.
2,
703.3
2,
2,
290.
681.
678.
309.
319.
780.
798. 6
2,
2,585.8
215; cf 119
191.
233.
78.
233.
i?
671.
674.8
710.4
963. 8
960. 5
943. 3
2,
2,
554.1
617.
619.
618.
345.7
410.8
P>* 617.
I
CeHioOe
1,
191; cf. 145.

145.
191.
233.
191.
145.
583. 6
581. 6
588. 7
10; cf. 180.
145.
08
22
178. 08
22
617.3
2,
581. 6
632.2
Dimethyl
trimethylene-a,
a-dicarboxylate.
158.08
30
826.9
3,
463.
827.6
175.
Dimethyl acetylmalonate. .
Dimethyl glutarate.
Dimethyl tetramethylene-
174. 08
28
32
36
752.8
863.2
983.5
3, 148.
769.0
866.7
983.8
78.
tartrate
178.
(s)
(s)___
160.09
172. 10
3,
10
612. 5
4, 119.
cf; 9.
10; cf. 180.
233.
175.
a, /S-dicarboxylate.
CsHiiO*
Dimethyl adipate
174. 11
38
C9H16O4
Dimethyl pimelate
Dimethyl suberate
Dimethyl azelate.
188.12
44
50
56
62
O0H18O4
C11H20O4
..
("Dimethyl sebacate .
\Dimethyl sebacate (s)
C12H22O4
C9H14O7
Trimethyl
Dimethyl pentamethylene-
l)
n 404
1
citrate
(s)
202. 14
216. 15
230.17
1,
019. 6
4, 267.
1,
176.
4, 921.
1,
333. 2
488. 3
1,
579. 4
1,
023.
233.
1,
179. 3
335. 6
233.
233.
233.
233.
233.
191.
175.
1,
1,
491. 9
648. 2
1,
993.9
127. 2
983.0
6,228.5
6,883.1
6, 845. 8
4, 113. 9
116. 6
4,
677. 4
4,
940. 8
1,
192. 3
185.
5,
131. 7
L237.8
185.
1,644.7
1,
635. 8
186. 11
36
42
1,
196.1
44
1,
180. 6
198. 11
46
1,
226. 2
234. 11
5,
1,
a/3-dicarboxylate.
C10H12O4
Dimethyl A-l,4-dihydrotere-
C10H14O4
Dimethyl A-tetrahydrotere-
phthalate
phthalate
The
(s).
1
(s).
heat of fusion of dimethyl fumarate
is 8.3, which would bring the calculated value to approxikg-cal.

of (10) is much more accurate than that of (145), and preference should be given to his values.
Tiie values of (145) are included here merely to allow one- to estimate the accuracy of his results and to
lise this information as a guide in estimating the accuracy of his measurements when no other measurements are available. His results vary widely. On the whole, they are not to be trusted to an accuracy
greater than 0.5 per cent, and in many cases the values are not better than 1 to 2 per cent.
17
mately 663.0
17
The work
Kharasch]

VIII.
2.
48.
:01
METHYL ESTERS OF POLYBASIC ALIPHATIC ACIDS Continued

Q=26.05XiV+16.5dd
NumMolec-
Name
Formula
ular
weight
Kg-calis
ber
of
elec-
trons
Kg-cali5
(experi-
Kilojoules
mental)
(K.
J.)
{N)
CioHuOs
Tetramethyl ethanetetracar-
doHieO*
Dimethyl norpinate (cis)

(Dimethyl 1,1-dimethyl-
boxylate
(calcu-
lated to
the
Literature
liquid
state)
262. 11
38
1,
045.
4, 373.
1,
056.
183.
200.13
48
1,
287.
5,
393.
1,
296.
175.
200.13
48
1,273.5
274. 11
42
1,
169.
(sym.).
(s)
cyclobutane-2,4-dicarboxylate)
C10H16O4
Dimethyl hexahydrotereph-
CnHuOg
Tetramethyl a, a, &, /3-trimethylenetetracarboxy-
C11H16O4
CiiH 18 04
Dimethyl
spiroheptanedicar boxy late.
Tetramethyl methylenedimalonate 18 (s).
Dimethyl a-tanacetonedi-
C11H18O4--
Dimethyl pinate
thalate (Jum)
late
CnHieOs
5,329.6
1,283.5
185.
4, 895.
1,
173. 2
187.
(s)
(s).
212. 13
52
1,
407. 7
5,
896.
1,
400. 6
175.
276. 13
44
1,
201.
5,
027.
1,
212.
187.
214. 14
54
1,
451.
6,
079. 9
1,
452. 7
175.
214. 14
54
1,
440. 2
6,
032.
1,
452. 7
175.
carboxylate.
i8(CH3.C02)2.CH.CH2.CH(C0 2 CH3)2.
49.
METHYL ESTERS OF POLYBASIC AROMATIC ACIDS

Q=26.05XiV+16.5dd-3.5a-6.5b
Dimethyl phthalate
-.. 194. 08
Dimethyl isophthalate (s).._ 194. 08
Dimethyl terephthalate (s)._ 194. 08
Trimethyl trimesate (s)
252. 10
Dimethyl diphenylmaleate 296.13
C10H10O4C10H10O4.
C10H10O4-
C 12 Hi20 6 C18H16O4-
42
42
42
48
80
119. 7
111. 1
4,
1,
4,
1,
1,111.6
4,
1,
1,
1,
685.
649.
652.
5, 405.
8, 838.
291. 7
2, 111.
1,
120. 1
120.
120. 1
289. 4
2,
120. 5
1,
191.
191.
191; cf. 185.
191.
183.
(s).
Hexamethyl mellitate
Dimethyl /3-truxillate
C18H18O12
C20H20O4-
19
This value
is
(s)
426. 13
(s)
324.16
not quite satisfactory, although

50.
it is
66
the
824. 3
2, 421. 6
19 1,
mean
of a
191.
183.
634. 7
10, 134. 4
7,
number
of determinations.
ETHYL ESTERS OF MONOBASIC ALIPHATIC ACIDS

Q=25.05XiV+16.5
C4H8O2.
74.0
74.05
88.0
Ethyl acetate
88.06
Ethyl
Ethyl
Ethyl
Ethyl
C5H6O2-.
C5H10O2C5H10O3-
C Hio0
Ethyl formate (v) .

Ethyl formate (liq).
Ethyl acetate (v)...
3-
(liq)..
propiolate
propionate
lactate
acetoacetate
398.4
391.7
544.4
14
""20"
(536. 9
1,
1,
2,
666.
638.
276. 7
223.
26; cf. 65.
537.5
2,245.3
\539. 9
2,
98.05
102. 08
118. 08
130. 08
22
26
24
28
634.8
690.8
653.3
753.6
2,
116. 10
116. 10
851.2
845.7
965.1
3,
128.10
32
32
36
172.
654. 7
2, 891.
2, 732.
3, 151. 6
635.7
654.7
755.4
75; cf. 118.
559. 7
3, 536. 7
8, 297. 9
850.1
850.1
967.3
118.
118.
175.
693. 8
C7H12O2-
Ethyl n-butyrate
Ethyl isobutyrate
Ethyl
tetramethylenecar-
C7H12O2-
Ethyl angelate
128.10
36
964.2
4,
035. 2
967.8
C7H12O2C7H12O2C 7 H,203C7H1203-
128. 10
954.4
971.5
926.1
923.4
3,
967.8
967.8
934.7
934.7
006. 4
C6H12O2-
I2
2-
223.
78.
257. 9
138.
172.
112.
boxylate.
C8H1202-
Ethyl
Ethyl
Ethyl
Ethyl
Ethyl
Ethyl
/3-ethoxyacrylate
valerate
sorbate
130. 11
140. 10
36
36
34
34
38
40
C8H12O4-
Ethyl diacetylacetate
172. 10
36
C H,40
7
20
,
2-
This value
is
tiglate (s)
allylacetate
a-ethoxyacrylate
(s).
128.10
144.10
144. 10
1,
20
1,
017. 5
012.
4,
4,
994.
065.
875.
864.
255.
239.
972.1
4,
065. 3
apparently too low and would bear reinvestigation
4,
3,
3,
7
7
4
1,
967.3
151.
151.
166.
166.
65.
162.
78.
402
Bureau
VIII.
2.
50.
Vol. 2

ETHYL ESTERS OF MONOBASIC ALIPHATIC ACIDS 3ontinued
Q=26.05XiVr+16.5
NumMolec-
Name
Formula
ular
weight
Kg-calu
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
J.)
the
Literature
liquid
state)
CsHhOs
CgHuOa
C10H16O2
CioH 16 02
C10H16O2
Ethyl a-ethoxycrotonate (s)

Ethyl a-ethylacetoacetate. _ _
Ethyl |8, 5-dimethylsorbate- -
158. 11
158. 11
168. 13
40
40
52
E thyl amylpropiolate
Ethyl (cyclohexene-1) -ace-
168. 13
52
52
1,
168. 13
1,
394.
360.
5,
168.13
52
1,
367.
5, 726.
1,
477.
6, 187.
1,
550. 8
501. 5
6,
1,
1,
1,
21
1,
076. 9
070.
351.
1,
481. 6
078. 8
1,
4, 506.
4,
6,
829. 7
698. 7
5,
091.
068.
166.
242.
162.
1,
404. 2
377. 6
138.
167.
1,
384.
1,
tate.
C10H16O2
Ethyl eye lohexylidene
C11H16O2
Ethyl 1-methylcyclohexene-
C11H18O2
C11H18O2
E thyl hexylpropiolate
Ethyl a-(cyclohexene-l)-
182. 14
182. 14
C11H18O3
propionate.
Ethyl methyl-l-ethyl-4-cyelopentanone carboxylate. 23
198. 14
1,
465. 8
6, 129.
215.
C12H18O2
Ethyl
194. 14
1,
631.
6,
833.
176.
167.
acetate.
180. 13
174.
l-methene-3-carboxylate.
l,3-Dimethyl-4-cy-
58
58
22
6,
485. 5
289.
1,560.5
138.
167.
clohexene - 3 - methene - 5 carboxylate.
2i
22
This value appears to be low.

This value appears to be low.
In the article by Swietoslawski (J. Amer. Chem. Soc, 40, p. 1099; 1920) the compound is named " ethyl
However, neither the empirical formula nor the
ester of methylethyl-l,4-cyclopentanecarboxylic acid."
molecular weight corresponds to the above name. The above formula is suggested, for it corresponds to
the molecular weight given.
23
51.
ETHYL ESTERS OF MONOBASIC AROMATIC ACIDS

Q=26.05XiV+16.5 -3.5a-6.5b
Ethyl benzoate
Ethyl salicylate
Ethyl p-hydroxy benzoate (s)
Ethyl phenylpropiolate
Ethyl a-methylcinnamate 24 _
Ethyl j8-methylcinnamate._ _
Ethyl methylcoumarinate. ..
CoHioOj..
C9H10O3--
C9H10O3C11H10O2C12H14O2C12H1.O2C12H14O3-
24
150. 08
166. 08
166. 08
174. 08
190. 11
190. 11
206. 11
42
40
40
50
58
58
56
1,
1,
1,
1,
1,
1,
1,
098.
051.
042.
338.
526.
527.
494.
7
2
8
6
8
5
2
4, 598.
399.
364.
5, 598.
6, 395.
6, 398.
6, 259.
4,
1,
4,
1,
1,
1,
1,
1,
1,
107.
055.
055.
345.
533.
533.
501.
9
9
3
205.
206.
206.
138.
163.
163.
177.
See also Ber., 25, p. 90; 1892, for heats of combustion of polymers of ethyl cinnamate.
52.
ETHYL ESTERS OF POLYBASIC ALIPHATIC ACIDS

Q=26.05XiV+16.5dd
C5H10O3
2,
642.1
716.0
860.4
2,
709.
685.
994.
598.
5
3
3
007. 3
930.6
931.3
957.6
212.
3, 894.
3, 896.
4, 004.
5
6
1,
328.
5,
561.
1,
335.
183.
1,
322. 9
5,
536.
1,
335.
9.
50
1,
324.
5,
541.
1,
335.
9.
54
1,
459.
6, 101.
1,
462. 7
118.
316. 16
60
1,
627. 7
6,
811.
1,
642.
183.
318. 18
62
1,
661. 2
6,
952.
1,
681.
326. 18
94
2,
450. 8
10, 256.
2,
474. 9
166.
326. 18
94
2,
449. 4
10, 250. 7
2S 474.9
166,
24
146.08
160. 10
26
32
08
38
34
34
34
1,
Diethyl d-tartrate.. .
Diethyl mesotartrate
Diethyl acetylenedicarboxy-
11
11
11
C8H10O4
174.
206.
208.
170.
C10H18O4
Diethyl
dimethylsuccinate
202. 14
50
C10H18O4
Diethyl
dimethylsuccinate
202. 14
50
C10H18O4
Diethyl
dimethylsuccinate
(meso) (s).
Triethyl citrate.. .
202, 14
276. 16
118.
C8H1404
CgHnOe
CsHuOe
215.
119.
119.
647.
08
Diethyl oxalate
Diethyl malonate
C6H10O4
C7H1204
2,
3,
4,
"~~723.T
2
1,
9
7
866.6
119.
022. 9
119.
931.7
931.7
9.
951.
138.
9.
(sym.).
(rac).
C12H20O7
C14H20O8
C14H22O8
C20H22O4
.-
Tetraethyl ethylenetetracarboxylate (s).

Tetraethyl
ethanetetracarboxylate (sym.) (s).
Diethyl diphenylsuccinate
(rac.) (s).
C20H22O4
Diethyl
(meso)
diphenylsuccinate
(s).
403
Kharasch]
VIII.
2.

ESTERS OF ALIPHATIC ACIDS
53.
(All types)
Q=26.05XiV+16.5dd
Number
Molec-
Name
Formula
ular
weight
of
elec-
trons
Kg-calis
Kg-calis
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
the
J.)
Literature
liquid
state)
C4H6O2C4H5O2-.
C5H8O2C7H14O2C12H20O2
Ci 8 3 60 2
C32H64O2
25
Allyl formate (v)

Vinyl acetate
Allyl acetate
Amyl acetate
Propyl hexylpropiolate
Cetyl acetate (s)
284.2
Cetyl palmitate
480. 51
The accuracy
than
of the
(s)
86.0
86.05
18
18
100. 06
130. 11
196. 16
24
method employed and the value
525.8
498.1
655.8
40
64
104
for
25
042. 5
717. 3
728.
4, 872. 8
1,
1,
2,
the
2,
2,
5
6
7
198.
084.
742.
4, 359.
7, 181.
2,
8
11,417.1
20, 392. 7
compound given
498.4
654.7
1,
1,
058.
716.
725.
4, 913.
2,
223.
164.
119.
158.
138.
183.
181.
are probably not better
per cent.
ESTERS OF AROMATIC ACIDS
54.
(All types)
Q= 26.05 XxV-f 16.5

C10H12O2
C10H12O3
C10H12O3
__
Propyl benzoate
Propyl salicylate
Propyl p-hydroxybenzo
ate
48
46
46
1,
254. 5
205. 7
200. 6
5,
180. 10
5,
250.
045. 9
024. 5
54
1,411.4
5,
906. 7
52
60
58
206
365. 5
1, 569. 5
1, 526.
5, 358. 5
164. 10
180. 10
Isobutyl benzoate
178. 11
C11H14O3
Isobutyl salicylate
Amyl benzoate
194.0
C12H14O2--!
C48H38O12-
1,
5,
1,
263. 4
214. 8
214. 8
205.
206.
206.
1,
419. 7
205.
1,
371.
576.
533. 9
206.
205.
163.
206.
1,
1,
(s).
C11H14O2
C12H16O2--
1,
Propyl cinnamate
Mannitol hexabenzoate
(s)_.
55.
192. 13
190. 11
806. 30
1,
714.
6, 568.
6, 392.
22, 425.
5,
6
4
4
1,
1,
PHENOL ESTERS
Q=26.05XiV+16.5-3.5a-6.5b+3.5m
C12H14O3
C12H14O3
C13H10O2
C14H12O2
C14H12O4
Ci5H 14
C16H16O2
C17H18O2
Eugenol acetate
(s)._.
206.11
Isoeugenol acetate (s).

Phenyl benzoate (s) .
p-Cresyl benzoate (s).
206. 11
198. 08
212. 10
Guaiacol salicylate (s)

o-Xylenyl benzoate (s)
Pseudocumenyl benzoate
fThymyl benzoate (s)
[Thymyl benzoate (liq.)
(s).
C17H16O3
Eugenol benzoate
CnHjeOs
Isoeugenol benzoate (s)

Ally 1-3, 4-guaiacol benzoate
(s) (Betel benzoate).
Resorcyl dibenzoate (s)
C17H16O3
C20H14O4
(s)
56.
C15H26O6
C15H20O8
Ci 8 H260 6
C24H20O6
C39H74O6
C45H86O6
C47H88O5
C47H88O5
CegHmO,
CegHmO,
1,
1,
64
1,
10
1,
11
13
1,
14
2,
1,
2,
497. 8
488. 2
510. 5
660.
6,
6,
589.
814.
967.
127.
131.
1,
1,
653. 3
592. 9
1,
318. 11
2,
196.
183.
205.
2,
142.
2,
2,
074. 4
071. 4
073. 9
196.
196.
196.
2,
266.
205.
8, 904.
2,064.3
638. 3
8, 599. 8
8, 639.
6
9
268.13
3
3
922.
8, 235.
064.
054. 9
1,
504.
501.
523.
680.
192.
205.
205.
205.
205.
7,
2,
1,
321. 4
6, 947. 5
6,
268. 13
268. 13
2,
268. 3
6, 228.
8,
1,
583.
829. 5
8,
237.
2,
GLYCEROL ESTERS
Glyceryl
Glyceryl
Glyceryl
Glyceryl
Glyceryl
tributyrate
tricyclobutyrate.
tricyclovalerate.
tribenzoate (s) _ _
Glyceryl
Glyceryl
Glyceryl
Glyceryl
Glyceryl
trimyristate
dibrassidate (s).
dierucate (s)
tribrassidate (s)
trierucate (s)
trilaurate
244.
226.
240.
254.
1,
(s)
302.
296.
338.
404.
638.
21
16
21
16
59
722. 69
732. 70
732. 70
1,053.02
1,053.02
1,941.1
1, 844. 9
308. 6
2, 718. 9
5, 706. 3
2,
650. 3
6, 953.
6, 979.
10, 235. 8
10, 264. 7
6,
8, 117.
715.
654.
11, 378.
23, 880.
4
6
6
9
7,
9,
27, 831. 5
29, 098. 3
29, 207.
42, 836.
42, 957. 8
215.
215.
215.
206.
193;
cf.
120.
193; cf. 120.

193.
193.
193.
193.
404
Bureau
Vol. 2

3. N COMPOUNDS
VIII.
ALIPHATIC AMINES (PRIMARY)
57.
Q=26.05XiV+13ee
NumMolec-
Name
Formula
ular
weight
Kg-cali5
ber
Kg-calu
of
elec-
trons
(calcu-
Kilo-
(experi-
joules
mental)
(K.
lated to
J.)
Of)
CH N
6
JMethylamine
Methylamine
C2H7N
C2H8N2.H2O
fEthylamine
(Ethylamine
31.0
(liq.)
31.05
45.0
45.07
256.9
261.4
256.1
413.1
408.5
78.10
57.0
57.07
59.0
59.08
452.6
528.1
524.8
572.3
558.3
73. 10
710.6
713.6
713.0
716.0
C3H7N
Ethylenediamine.
fAllylamine (g)
(Allylamine (liq.)
C3H9N
/Propylamine (g)
(Propylamine (liq-)
C4H U N
TC-Butylamine
Isobutylamine
Sec.-Butylamine
C4H11N
C4H11N
C4H n N
73.10
73.10
73.10
TerJ.-Butylarnine
C5H13N
Isoamylamine
1 1- Aminocyclopropylethane
Hexylamine
CsHnN
CeHisN
87.11
85.10
Benzylamine
107. 08
C7H15N
C7H17N
l-Methylcyclohexylamine-3 -
Heptylamine
C10H19N
Camphylamine
113. 13
115. 14
153. 16
1,
1,
1,
1,
1,
074.
092. 3
071.
727. 6
709. 6
403.Y
223.
99; cf. 15.
442.8
9
4
9
716.4
716.4
716.4
716.4
973.
2, 986.
2, 983.
2, 996.
2,
1,
118. 7
4,
1,
178. 9
533.
4,
4,
6,
678. 4
933. 7
416.
bomb
19.
223.
521.0
99.
223.
560.1
627. 6
443.
277. 9
4, 039.
4, 054.
3,
1,
99.26
894.
208. 6
3
2, 393. 4
2, 336. 5
1,
823.3
022. 2
965.8
969.4
1,
247.4
2,
2, 196.
calorimeter.
The author (99) used naphthalene to standardize his
The present best value is 9,617.0 cal./gfor naphthalene was 9,665.0 cal./gto be about 0.5 per cent too high, and they have accordingly been corrected
data are probably not of a high degree of accuracy.
27 See footnote 28.
26
223.
142.
872.6
833.5
3,
101. 13
C7H9N
Literature
state)
(g)
(g)
(liq.)
the
liquid
1,
99.
99; cf. 143.27
215.
028. 9
973.3
1, 133.
101.
147.
215.
1,185.3
1,
576. 9
However, the value he used

His values, thefefore, ought
by the proper factor. The
ALIPHATIC AMINES (SECONDARY)
58.
Q=26.05XiV+19.5
C2H7N-.
Dimethylamine
(g)_.
(Pimethylamine (liq)
{Diethylamine (g)
C4H11N-
C Hi N.
9
C9H13NC10H23N
ChHisN
Diethylamine
(liq)
_ _
Diisobutylamine
Benzylethylamine. .
D iisoamylamine
Dibenzylamine (s)_.
45.0
418.2
426.0
416.7
730.6
722.8
15
45.07
73.0
73.1
129.
135.
157.
197.
28
716. 9
16
1,
11
19
13
1,
348. 4
289. 6
660. 4
853.
1,
1,
4
8
9
6
9
3,000.2
749.
782.
743.
3, 057.
3, 024.
1,
1,
410.2
1,
5,
5,
6,
7,
643.
397.
948. 8
754. 8
722.
1,
1,
1,
1,
358. 1
292. 5
660. 5
869.
223.
142.
99.
223.
99.
143.
99.
28 Little significance should be attached to values of (143) for the redetermination of the heats of combustion of the three amines by the same author (142) some 25 years later showed enormous variations from
the values obtained previously. The values by (142) are, on the whole, too low.
59.
ALIPHATIC AMINES (TERTIARY)

Q= 26.05X^+26
C3H9N-.
CeHisN.
C12H27N
C16H33N
C21H21N
2
See footnote
Trimethylamine
(g).
59.0
Trimethylamine
(liq)
59.08
Triethylamine
Triisobutylamine
Triisoamylamine
Tribenzylamine (s)_.
101. 13
185. 22
227. 37
21
28.
2S7. 17
39
75
93
105
29 1,
579.
592.
2,
578.6
2,
036. 8
973. 6
459. 3
2, 762.
2,
4,
1,
8,
2,
10,
11,
423.
479.
421.
339.
259.
292.
559.
5
6
4
5
2
4
223.
142; cf. 15.
573.1
1,042.0
1, 979. 8
2, 448. 9
2, 761. 2
99.
99; cf. 143.
Kharasch]
405

3. N COMPOUNDS Continued.
VIII.
AROMATIC AMINES (PRIMARY)
60.
Q=26.05XiVr+6.5-3.5hh-3.5a-6.5b
NumMolec-
Name
Formula
ular
weight
ber
of
elec-
trons
Kg-calis
(experi-
Kilojoules
mental)
(K.
Kg-cali5
(calcu-
lated to
J.)
the
Literature
liquid
state)
Nj
C7H9N
C7H9N
C7H9N
C7H9NO
109. 07
p-Phenylenediamine
p-Toluidine
p-Anisidine
108.
(s)
._.
(s)__.
C 10 H
107. 08
107. 08
107. 08
123. 08
(s)
CsHuN
C9H13N
C10H9N
08
a-Naphthylamine
(s)
/3-Naphthylamine
(s)
121. 10
135. 11
143. 08
143. 08
184. 12
C12H12N2
C19H19N3O
o,p-Diaminodiphenyl
Triaminotriphenylcarbinol
184. 12
810.5
765.5
839.6
3,
29
32
760.0
843.4
3, 180.
37
37
37
35
964.3
965.3
958.4
924.0
4, 032.
4, 036.
108.
265. 9
263. 5
261.
4, 637.
1,
5,
297. 8
287. 8
5, 298. 2
1,
5,
1,
556.
560. 9
561. 8
483. 5
511.
6, 532. 4
6, 536.
10, 386.
31
\
I
C6H7NO
401. 2
396. 9
417. 9
812.
811.
816.
93.07
CeHYNT
43
49
49
49
1,
60 /
\
60
1,
1,
1,
1,
305. 18
1,
1,
2,
3,
3,
3,
529. 6
24.
963.3
963.3
963.3
934.2
147.
147.
147.
99.
1,
116. 2
268. 9
266. 4
266. 4
99.
99.
99.
99.
1,
562. 5
100.
1,
562. 5
147.
179.
008.
3, 866. 9
4,
6,
182.
99.
211; cf. 184,
147.
97.
(S).30
30 This
article also contains the heats of
rosaniline hydrochloride.
combustion
of rosaniline hydrochloride
and the hexamethyl-
AROMATIC AMINES (SECONDARY)
61.
Q=26.05XiV+13-3.5hh
C7H9N..
CgHnN.
C12H11N
C 16 Hi
doHnN
Methylaniline
Ethylaniline
107. 08
121. 10
Diphenylamine
(s)
37
43
169. 10
59
219. 11
219. 11
77
77
973.5
1,121.5
4, 071.
4, 693.
1,
/ 1,536.2
428.
6, 403.
8, 382.
8, 361.
9
9
6
6
1,
Phenyl-a-naphthylamine
PhenyHS-naphthylamine
(s)
(s)
1,530.2
2,
1,
003. 8
998.
6,
973.3
1,
1,
129. 6
542. 9
147; cf. 72.

99.
182.
998. 8
998. 8
99.
99.
99.
AROMATIC AMINES (TERTIARY)
62.
Q=26.05XiV+19.5-3.5hh
CsHnN.
Dimethylaniline
C10H15N
CigHisN
Diethylaniline
Triphenylamine
(s)
63.
Glycine
AMINO ACIDS
(s)
43
55
87
121. 10
149. 13
245. 13
si
Sarcosine
C3H7N02
Alanine
(N-methylgly-
(s)
4,
6,
267. 8
9,
2,
782. 4
074. 9
490. 7
1, 136.
1,
2,
448. 7
275. 3
182.
182.
182.
(ALIPHATIC)
75.05
89.07
15
} 89. 07
15
89.07
89.07
105. 07
15
15
13
C3H7N02
142. 7
1,451.6
1,
981.4
977.7
234.
233.
401.1
1,
678. 6
387.
389.
1,
622. 5
631. 2
387.5
387.5
343.7
1,
194.
241.
195.
cine)
(a-Aminopro-
(s)
pionic acid).
C3H7N02
C3H7N02
C H N0 3
3
The
(Z-Z-Alanine
d-Alanine
Isoserine
(s)
(s)
(s)
1,
1,
1,
66; cf.
64.
241.
241.
623. 2
623. 2
439. 8
general expression Q=2Q.05XN+a covers this class of compounds adequately.

no heat of fusion is available for this class, it is impossible to estimate the value of "a". It
31
94.
23,
241; cf. 66.
However, since
is
probably
6.5.
406
Bureau
AMINO ACIDS (ALIPHATIC) Continued
63.
NumMolec-
Name
ular
weight
ber
Kg-cali 5
of
elec-
trons
(experi-
Kilojoules
mental)
(K.
Kg-cali5
(calcu-
lated to
the
liquid
J.)
(N)
C4H7NO4
C4H7NO4
Vol. 2

3. N COMPOUNDS Continued
VIII.
Formula
Diglycolamidic acid
Z-Aspar tic acid
state)
396.1
384.9
1,
385.
383. 1
1,
1,
150. 10
132. 08
463.3
459.7
470.7
133. 07
133. 07
(s)
_.
(s)
133. 07
C4H8N2O3
C4H8N2O3H2O
C4H8N2O3
32
132. 08
C5H8N2O5
Glycylglycinecarboxylic acid
C5H11NO2
d7-a-Aminoisovaleric acid
C5H9NO4
CeHgNOc
Glutamic acid
Literature
657. 7
610. 8
198.
183; cf 23.
66.
1,
615.
601. 7
938. 9
922.
971. 8
1,
1,
1,
64.
194.
64.
66.
08
471.3
1,
974. 3
241; cf. 66.
117. 10
700.8
2,
935. 7
241.
147. 08
542.4
191.0
559. 6
2, 272. 1
2, 341.
142. 10
3,
176.
(s).
(s)
(Valine).
(act.)
(s)
Triglycolamidic acid
CCH10N2O2
C6H10N2O2
CCH11N3O4
C0H12N2O3
(s)
Alanine anhydride (s)

d-Alanine anhydride (s)
D igly cy Igly cine (s)
Glycylglycine ethyl ester
(s)
160. 12
786.4
786.0
709.8
803.2
(a-aminoisocap-
131.11
855.6
3,
580.
159. 11
917.4
3,
842.
095. 3
4, 588.
946.6
3,
142. 10
189. 12
294.
292.
973.
3, 364.
3,
2,
66; cf. 64.

198.
2
6
4
6
66.
66.
241.
66.
CCH13NO2
Leucine
C7H13NO3
Formyl-d, /-leucine
C8H16N2O3
C8H14N4O5
d-Z-Leucylglycine (s)
Triglycylglycine (s)
188. 15
246. 15
1,
C9H16N2O5
a-Carbethoxyglycylglycine
ethyl ester (s).
/3-Carbethoxyglycylglycine
ethyl ester (s).
Leucylglycylglycine (s)
232.15
1, 120.
4,693.4
66.
232. 15
1,
091. 9
4,573.9
66.
245. 18
226. 20
1,
333.
723. 8
5,
66.
7,
584. 4
220. 9
4,
000. 9
(s)
194; cf.
23.
241.
roic acid).
C9H16N2O5
C10H19N3O4 _
C12H22N2O2--
Leucineimide
(s)
(3,6-diiso-
(s)
1,
66,
241.
241.
965. 3
66.
butyl-2,5-diacipiperazine)
32
See footnote 74b.

64.
AMINO ACIDS
(Containing a phenyl radical)
C8H9NO2C8H9NO2C9H11NO2
C9K U N0
Phenylglycine
(s)
Anilidoacetic acid
Phenylalanine
Tyrosine (s)
(s)
(s)_._
65.
955.1
965.2
1,111.3
151.08
151. 08
165. 10
181. 10
1,
070. 2
4, 043.
CO.
655. 2
4, 474. 5
66.
4,
64; cf. 23.
AMIDES (ALIPHATIC)
Q=26.05XiV
CH3NO-.
CH4N2O.
Formamide.
Urea (s)
C2H3NO3.
Oxamic acid
C2H4N2O2C2H4N2O2-
Oxamide
C2H5NO..
45.03
60.05
(s)
Formylurea
Acetamide (s)
C3H4N2O4-
Oxaluric acid
C3H5NO3-
Methyl oxamate
Malonamide (s)
C3H6N2O2C3H6N2O2C3H6N2O3-
C3H7NO-C3H7NO2C3H8N2O33 The author
89.03
(s).
Acetylurea
(s)
(s)
(s)
Hydantoic acid (s).

Propionamide (s)._
Urethane (s)
Ethylurea (s)
(130.5) gives
88.05
88.05
59.05
132. 05
103. 05
102. 07
102. 07
118.07
105. 07
89.07
88.08
134.9
151.6
564.6
633.8
128.
132.
11
14
203.2
207.0
282.6
207.5
305.4
358.8
14
12
17
15
18
360.9
308.6
439.9
397.2
472.0
6
5
8
......
1,
64;
537.8
554.9
130.2
130.
850.4
865.7
208.4
182. 7
285.5
208.0
303.0
364.7
184.
130.
209.
130.
184.
184.
364.7
312.6
442.8
402.7
475.4
130.
130.
209.
184.
130.
868.4
1,
1,
1,
1,
1,
1,
1,
?09
156.3
278.
501. 6
510.
291.
840.
662.
975.
4
5
9
3
3
the heat of combustion of guanidine nitrate, CH6N4O3.
184
194,
407
Mkarasch]
VIII.
N COMPOUNDS Continued
3.
AMIDES (ALIPHATIC) Continued
65.
Q=26.05XiV
NumMolec-
Name
Formula
ular
weight
Kg-cali 5
ber
of
elec-
trons
Kg-calis
Kilo-
(experi-
joules
mental)
(K.
(calcu-
lated to
J.)
(N)
C4H7NO3
Ethyl oxamate
Creatinine
C4H8N2O2
C4H8N2O4
C4H8N2O4
Succinamide
C4H9NO
C4H9NO
-Butyramide
(s)_
Isobutyramide
(s)-_ ._ _._
113.08
1 16. 08
148. 08
148. 08
(s)
(s)
C4H9N3O2
Creatine (anhydr.)
C4H9N3O2.H2O- Creatine (cryst)
._
87.08
87.08
457.3
563.4
509.2
427.0
426.6
20"
16
18
23
23
/
\
131. 10
(s)
149. 12
Dimethylmalonamide
C5H10N2O2
._
"
(sym.)
Literature
state)
17
117. 07
(s)
C4H7N3O-.-.
the
liquid
1,
459.3
913. 8
6
2, 355.
1,
1,
786. 9
785. 3
596.0
595.9
2,
559.
555.
553.
2,
2,
494,
493.
342.
322.
314.
2,
2,
184.
64.
521.0
429.8
429.8
2, 131.
599.2
599.2
8
8
184.
54.
54.
209.
209.
194.
64.
194.
130.1
26
685.8
2,
870.
677.3
184.
29
38
43
751.5
994.8
3, 145.
Diethylmalonamide (s)
Amylpropiolamide (s)
101. 10
158. 12
139. 11
1,
150. 4
4, 810.
755.5
989.9
153. 2
209.
184.
138.
d-Tartaricdiethylamide
dZ-Tartaricdiethylamide
Mesotartaricdiethylamide. . _
Hexylpropiolamide (s)
204.
204.
204.
153.
14
14
14
13
40
40
40
49
1,
064.
084. 3
065. 3
308.
4,
008.
068.
068.
309. 5
54.
856.1
209.
209.
184.
209.
(s).
C5H11NO
C7H14N2O2
C 8 Hi 3 NO
C8H16N2O4
C 8 Hi 6 N 2 04
C HioN 04
C9H15NO
2
'..
1,
1,
1,
4, 163.
2
9
5,
453. 3
454.
458. 3
470.
3,
547. 2
4,
4,
1,
1,
1,
1,
1,
54.
54.
138.
ACID AMIDES (AROMATIC)
66.
Q=26.05XiVr-3.5hh
C7H7NO--
Benzamide
C7H7NO-.C7H S N 2 0__
C 8 H9NO._.
C9H7NO.-.
Formanilide
1,
847.6
861.0
879.6
010. 4
1,
095. 6
681. 1
4, 228. 5
4, 581. 8
179. 08
1,
012. 4
4,
4,
1,
4,
1,
121. 07
(s)
(s)
Monophenylurea
(s)
Acetanilide (s)
Phenylpropiolamide
(s)
121. 07
136. 08
135. 08
145. 00
CgHtcNOs-.
Hippuric acid
CoHiiNO-.
Propionanilide (s)
Benzoylalanine (s)
Benzoylsarcosine (s)
o-Toluylglycine (s) 34
149. 10
193. 10
193. 10
1.
C10H11NO3C10H11NO3C10H11NO3-
1,
167. 6
168. 1
179. 8
193. 10
1,
167. 7
C10H11NO3C10H11NO3C10H11NO3.
m-Toluylglycine (s)._
p-Toluylglycine (s)__.
Phenaceturic acid (s) -
193. 10
193. 10
1,
1,
CioHnNOi.
p-Anisylglycme
Phenacetin (s)
(s) 35 _
193. 10
209. 10
167.
167.
164.
135.
285.
o-Toluylalanine
p-Toluylalanine
Benzanilide (s)
(s)
(s)
(Benzoyl-
3, 603.
3
8S2. 2
3,
236.
1,012.4
1,
094. 7
138.
1,
018. 9
208; cf. 64,
glycine)..
C10H13NO2-
CuHisNOs.
C11H13NO3C13H11NO..
C13H12N2O.
C13H12N2O.
23.
Diphenylurea
Diphenylurea
(s)
(s)
(s)
(sym.)...
(unsym.).
C16H16N2O2
C10H11NO2C10H13NO3-
(sym.)...
Benzalhippuric acid lactone 36
Benzalhippuric
acid
(s)
C16II15NO3-
Benzoylphenylalanine
Succinanilide
(s)
1.
1,
1,
179. 11
1,
207. 11
207. 11
1,
197. 10
1,
212. 12
212. 12
1,
1,
1,
268. 15
249. 10
267. 11
1,
1,
1,
321.
319.
575.
612.
614.
886.
888.
4, 937.
4, 886.
4,
883. 9
5
9
2
4, 885.
5,
5,
5
5
5
970. 4
852.
848. 4
4,
4,
875.
750. 8
378. 6
531.
5, 522.
6, 593.
6, 746.
6, 756.
7
2
2
7
1,171.7
1,171.7
209.
208.
208.
208.
1,
175. 7
139. 6
1,
289. 4
208.
208.
208.
160.
1,
208.
209.
184.
184.
1,
1,
1,
1,
328.
328.
582. 1
608. 1
608.
1,
972. 8
184.
1,
852. 5
66.
66.
1.0
66.
1,
8, 246.
7,
758. 5
742. 9
7,
917. 6
7,
168.
175.
1, 175.
1, 171.
(a-Benzoylaminocinnamic acid). 37
34
35
35
CH3.C6H4.CONH.CH2.COOH.
H3CO.C6H4.CO.NH.CH2CO2H.
C H 5 CO.N C=CH.C H 5
6
C 6H
Ch
Ho
C(C0 H).HN.OC.C
2
369729
H5.
(s)._.
269. 13
73
408
Bureau
[Vol.2

VIII.
3.
67.
CYCLIC UREIDES, HYDANTOINS, PYRIMIDINES, PURINES

NumMolec-
Name
Formula
ular
weight
ber
Kg-calu
of
elec-
trons
Kg-calis.
(calcu-
Kilo-
(experi-
joules
mental)
(K.
lated to
J.)
the
liquid
Literature
state)
C3H2N2O3
Parabanic acid
C3H4N2O2
C4H2N2O4.H2O
C4H4N2O3
C4H5N3O3
Hydantoin
(s)
l(Oxayl-
114.04
212.4
100. 05
160. 05
128. 05
311.7
276.3
358.7
379.1
1,
730. 5
1, 706. 3
3, 435.
2,
130.
urea)
(s)
Alloxan (s)
Barbituric acid (s)
Aminobarbituric acid
143.
(s)
07
C4H6N4O3
Allantoin
C5H4N4O
Hypoxanthine
(6-Oxy-
136. 06
413.5
408.1
821.0
C5H4N4O
C5H4N4O2
8-Oxypurine (s)
Xanthine (s) (2,6-Dioxy-
136. 06
152. 07
591.8
514.6
(s) 38
158. 09
(s)
1,
1,
1,
304.
156.
501.
586.
2
5
1,
130.
130.
66; cf. 130.
130.
130.
64.
19.
purine)
476. 7
6
2, 153.
purine).
C5H4N4O3
Uric acid
C5H5N5O
C5H6N2O2
Guanine
C HeN
6
02
(s) 39
168. 07
(s)
4-Methyluracil
5-Methyluracil
(s)
(s)
(Natural
C6H6N2O3
"thymus").
Dimethyl parabanic acid
C5H6N4O4
C5H8N2O2
C 6 H 6 N4
Pseudouric acid (s)

4-Methylhydrouracil
7-Methylpurine (s)
7-Methylhypoxanthine
N40
C7H8N4O2
Theobromine
(s).
(s)
(s) _
(3,7-Dimethyl-2, 6-d ihy droxypurine)

C8H6N4O8.2H2O Alloxanthine (s)
CsHsNoOe
C 8 HioN40 2
Murexide
C8H12N2O3
C10H8N2O2
C12H14N4OG
C12H14N4O8
Veronal
(s)
(s)
Caffeine (s) (1,3,7-Trimethylxanthine)
1,
151. 01
126. 07
126. 07
586.4
566.1
564.8
142. 07
538.3
186. 10
128. 08
134. 08
454. 2
.150.08
618.2
821.0
759.9
180. 11
845.3
322. 12
284. 12
194. 12
583.9
735.9
1,
014. 2
1,
131.
322.
239. 3
925. 9
454.1
371.6
366.1
2,
252.
130.
900.8
589.8
435.9
180.2
3,
194; cf. 130,

64.
194.
241; cf. 66.
130.
66.
19.
19.
537.
130.
443.6
079.7
244.4
130.
130.
194.
184. 12
(s)
4-Phenyluracil. (s)
Desoxyamalic acid
(s)
Tetramethylalloxanthine
(Amalic acid).
(s)
310. 14
342. 15
1,
1,
4, 113.
66.
4, 737.
66.
5,
5,
533.
186. 5
130.
130.
38 The author
Note, however, that
(130) gives the heat of combustion of methylallantoin, C5H8N4O3.
the analysis for nitrogen shows a wide divergence from the calculated value. The values of (130) are open
No great reliance
to serious objections in that he used camphor to aid in the combustion of the substance.
should be attached to any of his values.
39 The author
(130) gives also the heat of combustion of ammonium urate, C5H7N5O3.
68.
C4H5N-
C4H6N2O2-
RING NITROGEN COMPOUNDS
Pyrrole
Diketopiperazine
cine anhydride).
(s)
(Gly-
67. 05
114.07
/'
C5H5N-.
C5H11N-
Pyridine
79.05
Piperidine
85.10
567.7
474.6
2,
658.
664.
2,
1,
375. 8
988.
826.6
755. 8
2, 782. 2
3, 459. 3
241; cf.
53.
57.
57.
'
C8H12N4-
C 6H
N.-
Hexamethylenetetramine
CH 7 N__
a-Picoline
0-Picoline
7-Picoline
C7H9N-
Lutidine
CH
H N0
5
2-
CsHrN...
C8H7NO2-
C HnN._
9
40
(s)
(Dimethylpyri-
dine).
Isatin (s) 41
The exact isomer not designated in

The author (1) gives also the heat
with zinc dust in acid solution, as
006. 7
4,
213.
55.
93.07
93.07
93.07
815.2
812.2
815.8
3,411.6
53.
399. 1
414.
53.
3,
107. 08
968.0
4,
051.
867.8
3, 631.
147. 05
117. 07
149. 07
135. 11
Indole (s)_
Dioxindol (s)
Tetrahydroquinoline
*o
140. 14
1,
1,
1,
3,
022. 2
4,
915.7
3,
228. 7
5,
53.
7
277. 9
832. 2
142.
article.
of combustion of isatide,
1,777.8 kg-cahs per mole.
C16H12N2O4. obtained by reducing
isatin.
VIII.
RING NITROGEN COMPOUNDS Continued
68.
NumMolec-
Name
Formula
ular
ber
of
elec-
weight trons
(N)
CH 9 N
...
C9H9N-...
C PH
409
Khamsch]
N....
C10H9N..C10H9N...
Skatole (3-Methylindole)...
Kg-calis
(experi-
Kilojoules
mental)
(K.
Kg-calis
(calcu-
lated to
the
J.)
Literature
liquid
state)
131. 08
131. 08
1,
1,
4, 891.
Quinoline
Phenylpyrrole (s)
Quinaldine (a-Methylquin-
129.06
143. 08
143. 08
170. 5
168. 7
123. 5
1, 283. 5
1, 287. 7
4,
a-Methylindole
1,
4, 701.
207. 08
1,
151.
4,
11
1,
08
10
2
2,
382.
475.
815.
348. 4
784.
6, 172. 9
7, 595. 8
9, 828.
898. 5
24.
24.
57.
371. 5
5, 389.
57.
183.
5,
oline).
C10H9NO4-
Opianic acid oxime anhy-
CioHi 3 N__
Tetrahy droquinaldine
C12H9N...
C16H10N2O
C20H27NO1
Amygdalin
dride
183; cf. 161
818. 6
(s).
Carbazole
Indigo (s)
147.
167.
262.
457.
(s)
(s)
1,
1,
5,
RING NITROGEN COMPOUNDS, IMIDES

Q=26.05XiVr-3.5hh
C4H5NO2--.
C5H7NO4--.
C6H9NO4---
C6H9NO4-C6H9NO4---
C8H 5 N0 2 -~
C10H9NO4
C10H9NO4
C10H9NO4
CnHnN0 CHH11NO4-CnHnN044
Succinimide (s)
<n-N-Methyltartrimide (s)
d-N-Ethyltartrimide (s)
dZ-N-Ethyltartrimide (s)
N-Ethylmesotartrimide
Phthalimide (s)
Hemipinimide (s)
d-N-Phenyltartrimide
(s)_.
70.
Coniine.
Nicotine
Papaverine (s)
Strychnine (s)
Narcotine (s).
Brucine (s)
Narceine (s)_.
71.
1,
077. 6
231.
1,
1,
1,
077.
240.
240.
240.
5, 179. 8
5, 192. 3
231.
231.
231.
231.
672.7
849.5
2,
099.
085. 7
4, 599. 3
4, 543.
085.
237.
237. 7
240. 7
4, 544.
5, 180.
207.
221.
221.
221.
08
10
10
10
1,
1,
41
1,
47
47
47
1,
1,
1,
1,
832. 6
2, 161.
2,
2,
3,
108;cf.l6L
1,
3
3
ALKALOIDS
339.
334.
413.
394.
481.
231.
184.
25
33
C20H21NO4
C21H22N2O2
C22H23NO7
C23H26N2O4
C23H27NO8.2H2O
17
670.7
852.6
159. 08
147. 05
127.
162.
303.
317.
311.
C Hi9N0
811. 9
555. 2
437.9
516.5
671.1
671.2
.H20. Morphine (s).

C18H21NO3.H2O.. Codeine (s)._ _.
Ci9H 2 iN0 3
Thebaine (s)._
C10H14N2
184; cf. 27.

231.
231.
231.
17
19
25
25
(Pyridine, Piperidine, Quinoline,
CsHitN
442.8
514.4
670.7
670.7
99.05
06
08
159. 08
207. 08
207. 08
dZ-N-Phenyltartrimide
d-N-Benzyltartrimide (s) . _
dZ-N-Benzyltaitrimide (s) ...
N-Benzylmesotartrirnide (s)
808. 6
809.
145.
159.
and Isoquinoline)
14
13
18
2,
20
2,
18
2,
18
2,
20
20
23
27
2,
1,
1,
2,
2,
2,
275.
427.
146.
327.
441.
5
7
3
6
3
478.
685. 7
644. 5
933.
802. 9
334.
974. 9
975. 8
9, 734.
10, 209. 5
19.
24.
5,
5,
106.
106.
106.
8,
10, 363.
11, 239.
11, 059.
12, 274.
11, 721.
4
7
3
106.
28.
106.
28.
106.
6
7
ALIPHATIC NITRILES
Q=26.05XiV+16.5
C2N2
Cyanogen
C2H3N....
Acetonitrile (v)
Acetonitrile (liq)
C2H3NO..
Gly collie
C3H2N2--C3H3NO2-.
Malononitrile (s)
Cyanoacetic acid
(s)
C3H4N2O.
Cyanoacetamide
(s)
nitrile
C3H5N-...
Propionitrile
Ethylidene lactonitrile
dehyde cyanhydrin),
H NO_.
5
41.0
41.03
57.03
258.3
262.1
310.4
302.4
256.7
84.05
85.03
84.05
55.05
71.05
394.8
298.8
376.3
456.4
421.1
52.0
(g)
(al
1,
1,
1,
1,
1,
1,
1,
1,
1,
080.
096.
298.
265.
074.
2
9
5
3
652. 2
250. 5
574. 8
910.
1,762.3
223.
10.
257.4
223.
102.
24.
397.7
303.0
381.2
459.3
420.2
41.
78.
78.
102.
24,
410
of Research
Vol. 2

VIII.
3.
ALIPHATIC NITRILES Continued
71.
Q=26.05X-?R-l6.5
Eg-cali5
Num-
Name
Formula
Molec-
ber
Kg-cali5
ular
of
elec-
(experi-
Kilojoules
mental)
(K.
weight
(calcu-
lated to
J.)
trons
Carbon subnitride
OiNi..
(s)
(acet-
76.0
the
Literature
liquid
state)
16
514.
2,
152. 9
545.7
574.9
581.5
671.9
2,
283. 7
406.
433. 6
393. 4
573.8
471.6
590.6
2,
2,
482.9
139.
554.0
576.6
676.6
576.6
41.
51.
51.
51.
576.6
475.8
61.
78.
198.
ylenedicarboxylic acid nitrite).
CiHYNTs..
C4H6N-,-..
Succinic acid nitrile

Allyl cvanide_
C4H5N
C4H N.._
Trimethylene
80.04
67.05
67. 05
67.05
nitrile
Crotononitrile
C4H5N
C4H5NO2
20
21
21
21
67.05
99.05
95. 07
21
17
69.07
94.07
23
26
613.3
699.6
Ethyl cyanoacetate.-.
113. 07
23
29
134. 09
630.0
772.1
846.0
C6H7NO3
Triglycolamidic nitrile (tri(cyanomethyl) amine) 44

Methyl acetylcyanoacetate
C6H9NO2
C7H9NO3
Propyl cyanoacetate
Ethyl cyanoacetylacetate
CsHnN
Amyl
CnHisNO
Cyanocamphor
Methyl cyancacetate
C4H5N3 -.-.-_
Diglycolamidic nitrite (di(cyanomethyl) amine). 43
C4H7N
C5H6N2...
ft-Butyronitrile
Glutaric nitrite
C5H7NO2
C HgN___
C H N4...
(s)
83.08
5
6
2,
2,
2,
1,
'
401. 4
973. 7
2, 471.
2,
566. 7
927. 8
615.6
710.3
102.
41.
2,
636. 6
635.1
771.9
78.
3, 231.
102.
198.
3,
540. 5
866. 7
693.7
78.
9
501. 2
868. 7
791.4
850.0
78.
141. 07
25
685.0
2,
29
789.0
836.6
3, 301.
(s).
127. 08
155. 08
43
57
1,
164. 2
4,
.__
121. 09
177. 05
1,
495. 4
6, 258.
(s).
42
(s)
31
The above value
an approximate
43
propiolic nitrile
represents the result of a single determination

value.
3,
1,
1,
169. 7
507.
78.
138.
42.
and should be considered merely
Considerable difficulty was experienced in the combustion of the compound due to
its
as
explosive
character.
44
N=(CH C=N)
2
AROMATIC NITRILES
72.
Q=26.05XiV-r-16.5nn-6.5pp
C7H5N-.
C 8 H 7 N-.
C 8 H 7 N..
C 8 H NO
5
Benzonitrile
103. 05
Benzyl cyanide
117.07
117. 07
131. 05
o-Toiunitrile
Benzoyl cyanide
(s)
. _ .
C9H7NO
Cyanoacetophenone
C9H5N-.
C11H7N-
Phenylpropiolic nitrile.
a-Naphthonitrile (s) . .
CnH N.
/3-Naphthonitrile (s).._
45
(s)
See formula for ketonic acids.

73.
145. 07
127. 04
33
39
39
35
1,
1,
3,
4, 283.
940.2
1,
"'11'
153.07
153. 07
865.5
023. 5
030. 3
1,
51
51
1,
1,
869.6
622.
1,
311. 8
3, 934. 7
1,
4,
029. 4
022. 4
937. 7
41.
41.
41.
78.
543.
4, 674.
5, 550.
5, 528.
2
6
2
4
328.
339.
996.
010.
3
6
319.6
475.9
98.
2,
593.
77.
632.2
788.3
944.8
77.
3,331.3
045. 5
77.*
085. 6
117. 8
326. 2
321.
4,
317.
320.
477.
480.
1,
78.
1,111.2
1,
1,
325. 5
325. 5
138.
102.
102.
CARBYLAMINES
(Aliphatic)
0=26.05X^+33.1C2H3N-
Methyl carbylamine.
41.03
11
H N_
Ethyl carbylamine-...
55.05
17
/
1
/
I
C4H5NC4H7N.
CfiHgN.
CeHuN
C 8 H N.
7
Allyl carbylamine
Propyl carbylamine..
Isobutyl carbylamine
Isoamyl carbylamine.
Benzyl carbylamine..
67.05
69.05
83.08
97.10
117. 07
609.1
639.6
796.0
949.5
21
23
29
35
39
1,
046. 5
1,
1,
2,
77.
77.
549.
2, 676. 7
973. 7
4, 379. 6
3,
1,
77.
77.
46 Th3 same article contains also the heats of combustion of double compounds of silver cyanide with
methyl, ethyl, propyl, isobutyl, isoamyl carbylamines, C3HaN2Ag to C7HnN2Ag.
The heats of combus
tion of these compounds are, within the limits of experimental error, rather uniformly about 503 kite'
j oules larger than the values for the carbylamines.
411
Kharasch]
VIII.

ISOCYANATES
74.
(Aliphatic)
=26.05X^+33.1
Kg-cahs
Num-
Name
Formula
Molec-
ber
Kg-cali5
ular
of
elec-
(experi-
Kilojoules
mental)
(K.
weight
(calcu-
lated to
the
liquid
J.)
trons
C2H3NO
C3H5NO
._
Methyl isocyanate
..
Ethyl isocyanate
75.
CeHyNO..
C6H6N2O3.
57.03
71.05
Literature
state)
269.4
424.5
9
15
1,
1,
127. 4
776. 5
267.6
423.9
96.
96.
HYDROXYLAMINE DERIVATIVES
Phenylhydroxylamine 47
m-Nitrophenylhydroxylam-
803.7
765.6
109. 06
154. 08
3,
3,
366. 7
204.
163.
164.
ine
47
The author
(163) does
not indicate which isomer

76.
is
burned.
ALIPHATIC NITRO COMPOUNDS

Q=26.05XiV+13
CH3NO2--
Nitromethane
C2H5NO2-.
C3H7NO2-
Nitroethane
Nitropropane
CioHi 5
a-Nitrocamphor
48
N0
This
61.03
75.05
89.07
197. 13
(s)
article contains also the heat of

77.
6
12
18
combustion
1,
of other
169.4
322.2
477.9
1,
371.
5,
708.4
1,
348. 4
998. 6
738.
169.3
325.6
481.9
212; cf. 36.

36.
212.
42.48
forms of nitrocamphor.
AROMATIC NITRO COMPOUNDS
Q=26.05XiV+13ss
C H N0 2 --.
C6H4N2O4
C6H4N2O4
6
Nitrobenzene
123. 05
28
o-Dinitrobenzene
(s)
168. 05
26
p-Dinitro benzene
(s)
168. 05
28
C6H4N2O4
m-Dinitrobenzene
(s) 50
168. 05
26
C6H3N3O6
CcHsNsOb
1,3,5-Trinitrobenzene
1,2,4-Trinitrobenzene
C19H13N3O6C19H13N3O7-
Trinitrotri phenylrnethane (s)

Trinitrotriphenyl carbinol(s)
(s)
(s)
213. 05
213. 05
379. 13
395. 13
24
24
86
84
2,
2.
739.2
732.4
703.2
695.1
692.0
696.8
694.7
091.
062.
2, 942.
2, 908.
2, 893.
2, 916.
2, 905.
3
9
9
663.7
673.7
777.
2, 817.
499.
9,
9, 270.
6
4
664.2
664.7
4
2
2, 279. 3
2, 230. 7
271. 5
216. 7
3,
3,
2,
742.4
72.
211.
703.3
703.3
33; cf. 72.

33.
703.3
33
211; cf. 72.

33; cf. 72.
72.
179.
179.
49 The heats of combustion of 1,3,5-trinitrobenzene, 2,4,6-trinitro-l-methylnitroaminobenzene, C7H5N5O8,

2,4,6-trinitrotoluene,C7H5N306, 2,3,4,6-tetranitro-l-methylnitroaminobenzene, C7H4N6O10, ammonium picC6H6N4O7, ammonium salt of hexanitrodiphenylamine, C12H8N8O12, and trinitroethane, C2H3N3O7,
used as explosives, are given by Rubtzov and Sever' yanov, J. Russ. Phys. Chem. Soc, 50, p. 140; 1918.
However, the results are valueless as far as accuracy is concerned, and, since the data in regard to the methods employed are entirely missing, the values have been omitted from this report.
50 The author (148) claims that by mixing m-dinitrobenzene and naphthalene no heat is evolved.
Certainly the lower heat of combustion 0.18 per cent obtained for the mixture is meaningless for individual determinations do not check better than 0.5 to 1 per cent,
rate,
412
Bureau
[Vol.

VIII.
3.
78.
SUBSTITUTED AROMATIC NITRO COMPOUNDS

Q=26.05XiV+13ss-3.5a
Kg-calis
Num-
Name
Formula
Molec-
ber
Eg-cahs
ular
of
elec-
(experi-
Kilojoules
mental)
(K.
weight
(calcu-
lated to
the
J.)
trons
C7H7NO2
C7H7NO2
C7H7NO2-
o-Nitrotoluene _. p-Nitrotoluene (s)-_._
C7H6N2O4
2,3-Dinitrotoluene
C7H6N2O4
C7EUN2O4
C7EUN2O4
137. 06
137. 06
=.
m-Nitrotoluene
state)
34
34
/
897.0
888.6
3, 751.
892.
889.
3,
34
182. 06
32
859.6
182. 06
182. 06
182.06
182. 06
182. 06
32
32
32
32
32
852.8
855.2
854.3
C7H8N2O4
2,4-Dinitrotoluene (s)
3,4-Dinitrotoluene (s)__
C7H5N3O6
C7H5N3O8
C7H5N3O6
C7H5N3O8
C7H5N3O6
2,4,6-Trinitrotoluene
30
30
30
30
30
820.7
832.9
825.6
828.1
823.8
3,
(s)
227.06
227. 06
227. 06
227.06
227. 06
C7H5N3O6
C H N 04
C H N204
2.3,6-Trinitrotoluene (s)
TO-/3-Dinitrostyrene (s)
p-/3-Dinitrostyrene (s)
227.06
194.06
194.06
825.3
957.4
962.6
3,
C9H11NO2
C9H11NO2
Nitromesitylene (s) .. __.

w-Nitromesitylene (s)
165. 10
30
36
36
46
46
C9H10N2O4
C9H10N2O4
C14H9NO4-
Dinitromesitylene (s)
w-o-D initromesitylene
p-Nitrobenzil (s) ..
p-Nitroacetyl benzoin (s)
2>-Nitrobenzoylbenzoin (s)___
210. 10
210. 10
255. 08
HN
6
04
CkJThNOs
C21H13NO5
(s)
(s)
(s)
(s)
165. 10
297.10
359. 11
All the values by (243) have been corrected according

Amer. Chem. Soc, 42, p. 1091; 1920.
52
44
44
60
70
92
3, 566.
1,
52 1,
600. 9
864. 3
443.
4
2,
1,
1,
to the
72.
817
817.0
817.0
817.0
817.0
72.
451.
4, 006.
4, 028.
5, 038.
4, 994.
4
7
72.
916.
4, 830.
6, 699.
7, 802.
10, 225.
4,
1,
817.0
970.3
970.3
200. 8
1,
208.
8
8
8
1,
due
is
79.
employed
161.
1, 161.
1, 589.
1, 852.
2, 422.
72.
72.
72.
72.
72.
72.
72.
226.
226.
243.
243.
7
7
243.
243.
8.w
5
8.
8.
method suggested by Swietoslawski,
(243) believes that the difference in the heats of combustion of these

to the fact that the compounds were not quite pure.
Details as to procedure
211.
432. 2
3, 483. 2
3, 452. 7
3, 463.
3, 445.
204. 7
194. 3
175. 7
155. 7
72.
'856.1
853.0
1,
72.
576. 5
572. 7
3, 596.
3, 567. 3
3,
859. 9
1,
856.1
856.1
856.1
856.1
72.
211.
211.
856,
3,
The author
cent,
63
895.2
895.2
895.2
716. 1
734.
3, 721. 6
3, 594. 9
3,
137. 08
(s)
Literature
liquid
two isomers,
J.
1.79 per
in obtaining the data are completely lacking in the paper.
AROMATIC NITROPHENOLS, PHENETOLES, NITRANILINES,

NITROACETANILIDES
Q=26.05XiVr+13ss+3.5m+6.5jj-t-13kk+19.5p
o-Nitrophenol
H N03.
m-Nitrophenol
p-Nitrophenol
26
(s)
2,
688.
2,
688.2
2,
881.
878.
880.
864.
869.
882.
880.
139. 05
26
139. 05
26
648.0
2,
709.
597.
2, 562.
4, 270.
4, 223.
4
8
7
5
1,
1,
621.
611. 8
021. 2
009. 2
1,
006.
4,
210.
3, 204.
3, 200.
3, 187.
(s)
\
[
C6H4N2O5.
2,4-Dinitrophenol
C8H3N3O7.
2,4,6-Trinitrophenol
C8H9NO3C8H9NO3.
o-Nitrophenetole
m-Nitrophenetole
C8H9NO3-
p-Nitrophenatole
C6H6N2O2.
o-Nitraniline
184.05
(s)
(s)
(Pic-
ric acid).
C6H 6 N
(s)
C6H6N2O2.
m-Nitraniline (s)
p-Nitraniline (s)
C7H8N2O2.
C7H7N3O4.
p-Nitromethylaniline (s)
2,4-Dinitromethylaniline
C7H6N4O6.
2,4,6-Trinitromethylaniline
C7H5N5O8.
Tetryl
(s).
24
f
2,
2,
2,
2,
}229. 05
22
167.
08
167. 08
38
38
167. 08
138. 06
138. 06
138.06
38
29
29
29
08
197. 08
35
33
924.3
884.5
3,
08
31
857.9
842.3
152.
242.
693.8
2,
688.3
684.4
686.2
\
I
C6H5NO3-
139. 05
(s)
8
9
689. 1
687.
C6H5NO3-
\
1,
765.8
765.2
761.0
693.8
693.8
2
7
654.7
72.
615.6
72.
1,
022. 4
022. 4
170.
211.
210.
1,
022. 4
771.4
771.4
771.4
865. 4
3, 698. 9
934.3
895.2
3,
587. 7
856.0
3,
522. 5
72.
131.
210.
72.
131.
210.
210.
210.
210.
211.
170.
72.
72.
72.
(s).
C8H7N5O8.
C8H8N2O3.
C 8 H N20
8 H 8 N20 3
8
287. 08
(s)
Methyltetryl
(2,4,6-Tri-
301. 10
nitro-N-nitroethylamline)
o-Nitroacetanilide (s)
m-Nitroacetanilide (s)
p-Nitroacetanilide (s)
180. 08
180. 08
(s)
180. 08
1,
37
37
37
009.
4, 220.
973.9
969.5
968.2
075. 8
4, 054. 5
4, 051. 9
4,
72.
72.
973.3
973.3
973.3
210.
211;
210.
cf.
131.
IDiarasch]
VIII.
413

AROMATIC NITROALDEHYDES
80.
Q=26.05XiVr+13ss+13r-3.5a
Kg-cahs
NumMolec-
Name
Formula
ber
Kg-cahs
ular
of
(experi-
Kilojoules
weight
elec-
mental)
(K.
(calcu-
lated to
J.)
trons
C7H5NO3
m-Nitrobenzaldehyde
81.
(s)
151. 05
the
Literature
liquid
state)
800.4
30
804.0
3, 349.
131.
AROMATIC NITRO ACIDS

Q = 26.05X -ZV+13ss-3.5a-f-13e
C7H5NO4
o-Nitrobenzoic acid
C7H5NO4
m-Nitrobenzoic acid
C7H5NO4
C9H7NO4
C9H7NO4
C9H7NO4
p-Nitrobenzoic acid
(s) . _
167. 05
(s) .
167.05
(s)._
o-Nitrocinnamic acid
728.3
728.3
999.0
995.6
996.5
167. 05
(s).
193. 06
m-Nitrocinnamic acid (s)

p-Nitrocinnamic acid (s)
193. 06
193. 06
82.
729.8
735.0
726.4
729.1
3,
3,
3,
049.
3,
047.
045.
180.
166.
170.
3,
4,
4,
4,
738.9
131.
151.
738.
58.
9
8
8
6
738.
054. 2
078. 9
3, 039.
151.
1,
1,
1,
009. 4
009. 4
009. 4
151.
226.
226.
226.
PHENYLHYDRAZONES AND OSAZONES
The two
articles by Ph. Landrieu, Compt. rend., 141, p. 358; 1905; 142, p. 540; 1906, contain the heats of
combustion of the phenylhydrazones of the following aldehydes and ketones: Acetaldehyde, acetone,
furfuraldehyde, benzaldehyde, salicylaldehyde, acetophenone, anisaldehyde, benzophenone,

benzoin, benzil; the phenylhydrazones of the following sugars: Arabinose, glucose, galactose, levulose,
lactose; the osazones of glyoxal, diacetyl, benzil; and of the following sugars: Arabinose,
xylose, glucose, levulose, mannose, galactose, maltose, lactose. The data are not included in the tables,
for the information given in the above articles in regard to the work is extremely meager, and a careful
analysis of the values indicates that they do not form a homogeneous series.
diacetyl,
mannose, maltose,
83.
C2H5NO
C3H7NO
54
The
Acetoxime
ALDOXIMES (ALIPHATIC)
340.6
490.5
59.05
73.07
(s)
1,424.4
2,
051. 3
93."
93.
compare these values of (93) with those of (215) for methyl ethyl ketoxime,
former's values appear to be about 0.8 per cent too high.
It is of interest to
84.
Methyl ethyl ketoxime
C10H17NO
Camphoroxime
Cycloheptyl methyl ketox-
ime
646.5
651.0
2,
155. 15
1,
363. 5
5,
167. 15
1,
480.
6,197.2
2, 703.
724.
702.
(s).
(s)
C4H0NO.
KETOXIMES (ALIPHATIC)
C4H9NO.
C s Hi 7 NO.
215.
93.
215.
414
Bureau
Kg-calis
Num-
Name
ber
ular
of
(experi-
Kilojoules
weight
elec-
mental)
(K.
Kg-calis
J.)
trons
H N02
Benzoquinone oxime (p-Ni-
Vol. 2
AROMATIC ALDOXIMES AND KETOXIMES
Molec-
Formula
VIII.
85.
(calcu-
lated to
the
Literature
liquid
state)
123.05
713.5
2,
121. 07
135. 08
173. 07
907.2
3, 793.
1.
054.
163.
4.
1.
173. 07
1,
167. 4
4,885.6
225; cf. 222.
173. 07
1,
166.
4.
882.
225; cf. 222.
4,
331. 8
626.
5,
822.
573. 6
803. 3
108.
225; cf. 222.
225; cf. 93.
985.
226;
cf.
222.
trosophenol)
C7H7NO
C H NO
8
Benzaldoxime (s)
..
Methyl phenyl ketoxime (s)_
a-Naphthoquinone
oxime
C10H7NO2
(s)
4,
93.
93.
409.
868.
225; cf. 222.
(a-Nitroso-a-naph-
thol).
C10H7NO2
/S-Naphthoquinone
(s)
oxime
(/S-Nitroso-a-naph-
thol).
C10H7NO2
oxime
/S-Naphthoquinone
(s)
(a-Nitroso-/3-naph-
thol).
Oxime of opianic
anhydride 55 .
C10H13NO2
Thymoquinone oxime
CisHuNO
Diphenyl ketoxime
55
1, 152.
179. 11
197. 10
(s)
(s)
1,
1,
Stohmann, communicated by Liebermann (Ber., 25, p. 89;

He does not specify whether the above value refers
not indicated.
86.
C2H6N20
CSH10N2O
Ci2HieN20
Dimethylnitrosamine
Ethylphenylnitrosamine
Diphenylnitrosamine (s)
66 See also article

tetramine.
by Delepine
74.07
(s).
150. 10
198. 10
1,
1,
(C. R., 123, p. 650; 1896) for nitroso
88.
394.5
1,650.9
118. 4
532. 6
4,
6,
680.
413.
212.
212.
132.
and nitro compounds of hexaruethylene
NITRAMINES
Ethylnitramine "__._
w CH3.CH2.N H.NO2.
Formula and molecular weight

volume or constant pressure.
to constant
NITROSAMINES58
87.
C2H6N2O2
1892.)
6,
372.5
90.06
1,557.8
211.
NITROSO COMPOUNDS
C6H-1N2O4
Dinitrosoresorcinol (s)_
CgKioN 2
p-Nitrosodimethylaniline
168. 05
150. 10
5" 1,
582.
124.
4,
437. 8
706.
212.
212; cf. 132.
198. 10
1,
526.
6,
385. 5
132.
58
2,
(s).
C12H10N2O
2>-Nitrosodiphenylamine
(s).
58 The author (212) gives as the mean value 3,473 cal/g.

In his calculation of the molecular heat of combustion he employs 186 as the molecular weight instead of 168.05. The article contains, also, the heats
of
compounds
with
nitrous
acid.
For a detailed treatment of this subject
of reaction of a large number
consult Ber., 43, p. 1470; 1910; 44, p. 2429; 1911.

m The author (212) gives also the heat of combustion of nitrosodimethylaniline hydrochloride as 4j687.2
kilo-joules.
89.
AZO COMPOUNDS
555. 2
6,
1,552.6
6,
545. 9
502.
6.
574.
597. 4
6,
1,
1,
796. 4
C12H10N2-
Azobenzene
182. 10
(s).
C12H11N3
p-Hydroxyazobenzene (s) _ _
p-Aminoazobenzene (s)
C I2 Hi2N4-..
2,4-Diaminoazobenzene
C14H14N2O2C16H18N2O2-
p-Azoanisole
C12H10N2O.
(s)
198. 10
197. 12
212. 14
1,
1,
1,
1,
6,
6,
508.
497.
469.
285.
587.
685.
5
6
6
9
2
147.
100.
217.
101.
101.
101.
(Chrysoidine).
60
p-Azophenetole
Undoubtedly the best value
(s)
is
that of (217),
242. 13
270. 16
2, 100.
7,
8,
517. 9
788. 5
101.
101.
Kharasch]
VIII.
415

3.
SUBSTITUTED HYDRAZINES
90.
Kg-calis
NumMolec-
Name
Formula
ular
weight
ber
Kg-calis
of
elec-
(experi-
Kilojoules
mental)
(K.
(calcu-
lated to
J.)
trons
Phenylhydrazine
(s)
Literature
state)
/
\
108. 08
(s)
Methylphenylt^drazine
C7H10N2
the
liquid
122. 10
1,
875.
805.
038.
663. 6
370. 6
344. 5
100.
147.
100.
6,
684. 7
690. 9
100.
147.
3,
275. 2
3,
3,
4,
(asym.).
f 1, 597. 3
\ 1,598.8
184. 12
DIAZONIUM COMPOUNDS
91.
C6H5N3O3
Benzenediazonium
nitrate
92.
167.07
782. 6
AZOXY COMPOUNDS
/ 1,534.5
I 1,530.1
1, 903. 4
2, 098. 4
198. 10
C14H16N40
m-Azoxytoluidine
C 6Hl8N203_p-Azoxyphenetole
C16H18N2O3- .. o-Azoxyphenetole
93.
256. 17
286. 13
286. 13
(s)
(s)
(s)
2,
088.
Ethyl nitrite (v).._

Ethyl nitrate (v)._.
75.0
91.0
C3H5N3O9.
Trinitrogly cerol
Isobutyl nitrite (v)
227. 06
332.6
322.4
432.4
103.0
644. 6
4.
94.
71-Heptyl fluoride
n-Octyl fluoride (from bromide)

n-Octyl fluoride (from io-
101.
147.
101.
101.
101.
1,
1,
390. 9
348. 3
1,809.6
2,
695. 7
223.
223.
81.
223.
FLUORINE COMPOUNDS
17
7,
FLUORO-HYDROCARBONS (ALIPHATIC)
C7H15F
6,
HALOGEN AND SULPHUR COMPOUNDS

(a)
421. 9
403. 5
965. 7
8, 781.
8, 730.
6,
ESTERS OF NITRIC AND NITROUS ACID
C2H5NO2C2H5NO3-
C4H9NO2-
6,
118. 12
132. 13
1,
121. 5
271.
1,
266.
1,
4,
5,
690.
315. 3
211.
211.
3.1
211.
CsHnF
132. 13
dide).
The B. P.
mide.
of the product prepared from the iodide

See also Ber., 55, p. 3378; 1922.
C6H4F2
C7H7F...
C7H7F...
C7H6F2
C7H5F3.
C9H11F
_..
p-D ifluor obenzene

o-Fluorotoluene
Fluoropseudocumene
(C)
C2H5OF.
C2H4OF2-
Fluoroethanol..
Difluoroethanol.
than the one prepared from the bro-
96.05
747. 2
114. 05
110. 05
706.1
2,
903. 2
3, 777.
903.0
856.9
810.3
3,
208. 5
5,
110. 05
128. 05
w-Difluorotoluene (s)
w-Trifluorotoluene (s)
_..
0.6 higher
FLUORO-HYDROCARBONS (AROMATIC)
(B)
CHF
is
05
138.1
146.
(s)
1,
3,
3,
388. 7
053.
211.
211.
211.
211.
211.
211.
211.
214. 5
027. 9
211.
211.
3, 124.
952. 9
2
776. 3
583. 6
FLUORO-ALCOHOLS (ALIPHATIC)
G4.C5
82.02
290.4
245.8
1,
1,
416
Bureau
4.
VIII. TABLES OF DATA Continued

HALOGEN AND SULPHUR COMPOUNDS -Continued
94.
FLUORINE COMPOUNDS Continued

FLUORO-PHENOLS
(D)
Kg-calis
(calculated to
Num-
Name
Formula
Molec-
ber
Kg-cali5
ular
of
elec-
(experi-
weight
mental)
Kilojoules
(K.
J.)
trons
6 H 5 OF.
6 H 5 OF.
CeHsOF.
o-Fluorophenol
m-Fluorophenol
p-Fluorophenol
C7H5OF3
modif., M. P. 48.2).
Trifluoro- 7/1-cresol
C
C
(Stable
(s)
Ethyl
CsHoOF...
705.8
696.6
2,
2,
2,
499.9
455.5
106. 05
124. 05
951. 7
913. 2
913. 2
3, 192.
1,
090. 6
904.
211.
211.
3,
057.
211.
2,
ETHERS OF FLUORO-ALCOHOLS
fluoroallyl ether
731.0
104. 07
ETHERS OF FLUORO-PHENOLS
(G)
CsHsOF
112. 05
112. 05
112. 05
763.4
Fluor oethyl acetate

Difluoroethyl acetate
(F)
CjHgOF
state)
ESTERS OF FLUORO-ALCOHOLS
(E)
C4H7O2F
C4H6O2F2
m-Fluorophenetol
p-Fluorophenetol
140. 05
140. 05
(H)
1,023.1
1,019.9
78.02
96.02
C2H2O2F2
4, 265.
211.
211.
714.3
562.9
211.
211.
170.8
134.6
FLUORO-ACIDS (AROMATIC)
(I)
C7H5O2F..
C7H5O2F..
C7H5O2F-.
C8H5O2F3.
o-Fluorobenzoic acid (s)

m-Fluorobenzoic acid (s)
p-Fluorobenzoic acid (s)
C9H7O2F..
a-Fluorocinnamic acid
m-w-Trifluorotoluic
4, 278.
FLUORO-ACIDS ALIPHATIC
CI2H3O2F
140. 05
140. 05
140. 05
acid
61a
190. 05
740.2
737.6
739.7
807.1
3,
013. 6
4,
095.
084.
093.
3, 375.
3,
3,
5
6
4
(s).
61a
(s)___
166.
06
1,
238.
77i-F;$C-C6H4.COOH.
(J)
C4H7O2F-.
C4H6O2F2.
C9H9O2F..
C10H9O2F.
ESTERS OF FLUORO-ACIDS (ALIPHATIC)
Ethyl fluoroacetate.-.
Ethyl difluoroacetate.
(K)
503.1
436.5
106. 05
124. 05
2, 103.
1,
825. 4
4,
4,
433. 3
966.
1,
045. 5
ESTERS OF FLUORO-ACIDS (AROMATIC)
Ethyl p-fluorobenzoato
Methyl
(s)..
a-fluorocinnamate
168. 05
180. 05
1,
1,
060.
187. 5
(s).
(L)
C 2 H'40NF_
C2H3ONF2.
the
liquid
Fluoroacetamide (s) .
Difluoroacetamide (s).
FLUORO-AMIDES (ALIPHATIC)
77.05
95.05
250.0
208.3
871.1
417
Ehamsch]

HALOGEN AND SULPHUR COMPOUNDS Continued
VIII.
4.
94.
FLUORINE COMPOUNDS Continued

FLUGRO-AMIDES (AROMATIC)
(M)
Kg-calis
Num-
Name
Formula
Molec-
ber
Kg-calis
ular
of
elec-
(experi-
Kilojoules
mental)
(K.
weight
(calcu-
lated to
the
J.)
CSH7ONF2
C9H8ONF3
Difluoroacetanilide (s)
m-Trifluoroacettoluide
(N)
C2H5NF2.
C4H7NF4.
(s) .
_.
C2H4O2N2F2.
C IT402NF.
5
C3II3O2NF2
C6H3O4N2F
951. 2
362. 7
211.
211.
2,
363. 8
367. 4
211.
211.
1,
215. 3
211.
2,
958.
954.
939.
814.
799.
211.
211.
211.
211.
211.
771. 5
3, 226.
211.
778.2
771.1
782.2
3, 254.
4
8
2
211.
211.
211.
978.1
978.9
4, 090.
4
8
211.
211.
21
211.
211.
944.8
3,
043. 2
4,
81.05
145. 06
326.1
566.1
1,
126. 06
(s)
290.i
22.4).
(P)
C6H4O2NF.
C6H4O2NF-
1,
FLUORO-NITRAMINES (ALIPHATIC)
Dinuoroethylnitramine
(M. P.
state)
FLUORO-AMINES (ALIPHATIC)
Difluoroethylamine
Tetrafluorodiethylamine.
(O)
171. 06
203. 75
Literature
liquid
trons
FLUORO-NITROBENZENES
o-Fluoronitrobenzene
ra-Fluoronitrobenzene
p-Fluoronitrobenzene (s)
141. 05
141. 05
141. 05
l,4-Difluoro-2-nitrobenzene
4-Dinitro-l-fluorobenzene
159. 04
707.5
708.4
703.0
673.1
186. 05
2,
2,
2,
2,
2,
9
9
(s).
(Q)
C7H4O2NF3-
FLUORO-NITROTOLUENES
191.05
?tt-Nitrobenzotrifluoride
(R)
CeHoNF.
C 6 H 6 NF.
CeHoNF.
FLUORO-ANILINES
o-Fluoroanilinem-Fluoroanilinep-Fluoroaniline.
111. 05
111.05
111.05
(S)
CgHsONF
m-Fluoroacetanilide (s)
p-Fluoroacetanilide (s)
C 8 HsONF
(T)
CcH
C H8
4
NF
NF
CcH
F._..
C8H7O3N2F
3, 271.
FLUORO-ANILIDES
153.07
153.07
4, 093.
FLTJORO-NITROPHENOLS AND NITROPHENETOLES
3-Nitro-4-fluorophenol (s)__.
3-Nitro-4-fluorophenetol (s).
(U)
3, 249.
157. 04
185. 07
652.8
981.4
2,
730.
4, 104.
FLUORO-NITRANILINES AND NITRACETANILIDES
3-Nitro-4-fluoroaniline (s)_..
3-Nitro-4-fluoroacetanilide- _
156. 04
198. 06
736.9
936.2
3,
3,
081. 7
915. 2
211.
211.
418
Bureau
4.

HALOGEN AND SULPHUR COMPOUNBS- -Continued
CHLORINE COMPOUNDS
95.
(A)
CHLORINATED HYDROCARBONS
62
Kg-calis
Num-
Name
Formula
Molec-
ber
Kg-cali5
ular
of
(experi-
Kilojoules
elec-
mental)
(K.
weight
(calcu-
lated to
J.)
trons
CHsCl
Methyl chloride (g)

Methylene chloride
CH2CI2
85.0
119.5
CHCI3
CCl*
Carbon tetrachloride (v)_

\Carbon tetrachloride (liq.)-
(v)
(liq.)
C2H5CI
Ethyl chloride (v)___
C2H4CI2
Ethylene chloride
64.5
99.0
(v)
164.2
173.2
106.8
70.3
89.2
223.
724.8
14.
40.
293.9
373.3
223.
17.
223.
1,
324. 4
368. 1
133. 3
271.1
1,
133. 7
267.
1,
1,
99.0
237.0
62.5
166.0
110.0
281.5
162.5
1,117.8
460.4
1, 177. 2
680.1
78.5
112.9
478. 3
2,
427.8
1,
C3H5CI
C 3 H^C1
Propyl chloride (v)

Dimethyldichloromethane
(Acetone chloride) (v).
Chloropropylene (v)
1,838.0
Allyl chloride (v)
C3H4CI2
Diehlorotrimethylene
76.5
111.0
439.5
440.8
426.0
C2H3CI
C2CI4
C3H7CI
C3H6CI2
c-
C4H9CI
Tsobutyl chloride
o-Dichlorobenzene (s)
Hexachlorobenzene (s)
Benzyl chloride
Camphene hydrochloride
92.5
147.0
285.0
126.5
172.5
Terpilene dilrydrochloride.-Terebenthene hydrochloride
209.0
172.5
Cl2
CgCIg
C7H7CI
CioHieHCL.
C10H10.2HCI
CioHieHCL.
1,
1,
1,
17.
186.2
156.1
44.5
37.3
316.7
326.9
271.0
("Ethylidene chloride (v)___
C2CI6
Literature
446. 9
\Ethylidene chloride (liq..).

Hexachlor oethane (s)
Chloroethylene (v)
Tetr achloroethylene
C2H4CI2
the
liquid
state)
50.5
(v).
/Chloroform
\Chloroform
[Vol.2
000. 3
789.
17.
14.
223.
223.
40.
17.
223.
17.
223.
223.
223.
1,
843. 4
782. 8
36.
635.5
671.8
509.0
886.4
469. 8
2,
657. 7
223.
467. 7
469. 2
6, 137.
6, 144.
9
2
32.
32.
617. 3
348. 5
6, 763.
179.
179.
1,
2,811.5
2,
130. 2
3, 706. 9
6, 146. 7
17.
17.
179.
32.
(cryst.).
13
Diphenylchloromethane (s)_.
Triphenylchloromethane (s)
HnCl....
C19H15CI....
202.5
278.0
1,
2,
9,
821. 4
62 These compounds are not arranged in classes, but are given according to the number of carbon atoms
they contain. In view of the relativity large error in the determinations, the molecular weights are all
rounded off. All the data except Thomsen's determinations, or unless otherwise indicated, refer to the
formation of a dilute solution of hydrochloric acid. Thomsen's determinations are calculated to the production of gaseous hydrogen chloride. No vacuum correction was applied to any of the values. It is
impossible to calculate the heats of combustion of these compounds with any degree of precision, for the
amounts of water used in the respective combustions are not specified by any of the writers (except Thomsen) and, hence, it is impossible to correct the values for the heat of dilution of the hydrogen chloride
formed.
63 HCl-gas.
4 HCl-gas.
(b) compounds of c, h, o and cl (aliphatic)
C2H30C1
C2H302C1
C2H02C13
C4H702C1
C4H602C12-
Monochloroacetaldehyde
Monochloroacetic acid (s)
Trichloroacetic acid
(s)
Ethyl monochloroacetate
Ethyl dichloroacetate
(c)
Benzoyl chloride
C7H502C1
C7H502C1
C7H40C12
o-Chlorobenzoic acid (s)

p-Chlorobenzoic acid (s)
o-Chlorobenzoyl chloride
C7H502C1
Chlorosalicylaldehyde 65
o-Toluyl chloride (s)
Phthalyl chloride (s)
Ethyl o-chlorobenzoate
C 8 H 0C1
7
CSH402C12
C9H902C1
The
position of the chlorine
122. 5
157.
COMPOUNDS
C7H50C1
._
atom
234.4
171.0
92.8
493.9
463.4
78.0
94.5
163.5
(s)
980.3
715.6
388.4
2,
1,
065. 5
937. 9
O AND CL (AROMATIC)
c F C, H,
140.5
156.5
156.5
175.0
782.8
734.5
726.6
741.5
273.
071.
038.
3, 100.
156.5
154.5
203.0
184.5
746.3
944.0
801.8
3, 121.
065. 8
4,
in the molecule
157.
36.
36.
157.
157.
is
1,
not given.
3,
3,
3,
3,
7
7
6
947. 8
3, 353.
457. 2
157.
157.
157.
157.
157.
157.
157.
157.
419
Khamsch]

VIII.
4.
95.
CHLORINE COMPOUNDS Continued

(D)
CHLOROHYDROQUINOLS
Kg-cali5
Num-
Name
Formula
Molec-
ber
Kg-ealis
ular
of
elec-
(experi-
Kilojoules
mental)
(K.
weight
(calcu-
lated to
the
J.)
CCH5O2CI
Chlorohydroquinol (s)
2,6-Dichlorohydroquinol (s).
Trichlorohydroquinol (s)
Tetrachlorohydroquinol (s)_.
CeH40 2 Cl 2
C6H3O2CI3
C6H2O2CI4
(E)
CGH2O4CI2
Chloranilic acid
Chloroquinone
C0H2O2CI2
C6HO2CI3C6O2CI4-.
2,6-Dichloroquinone
Trichloroquinone (s)
state)
645.9
614.1
593.0
562.8
144.5
179.0
213.5
248.
703.
568. 2
4S1. 7
2, 355. 3
2,
2,
2,
222.
222.
222.
cf. 222.
225;
225;
225;
225;
cf.
225;
225;
225;
225;
225;
cf.
cf.
cf.
CHLOROQUINONES
209.0
142.5
177.0
211.5
246.0
(s)
C8H3O2CL
Literature
liquid
trons
(s)
(s)
Tetrachloroquinone(s)
2,
616.6
578.9
546.4
517.7
2,
2,
2,
2,
029.
580.
422.
286.
166.
3
5
7
7
222.
222.
222.
cf. 222.
cf. 222.
cf.
cf.
(Chloranil).
(f)
C2H40NC1
C2H20NC13-
chlorine compounds of
Chloroacetamide (s)._.
Trichloroacetamide (s)
96.
CH Br.
C H Br.
Methyl bromide
CsH
Propyl bromide
66
Br.
h, o,
242.5
165.2
93.5
162.5
n
1,
014.
690.9
157.
157.
ALKYL BROMIDES
184.
95
(v).
Ethyl bromide (v)_.
c,
180.4
340.5
329.5
497.3
109.0
(v)
123.
See footnote 62, p. 418, under chlorinated hydrocarbons.

bromine derivatives is bromine vapor.
The
final
1,
1,
2,
769.5
754.9
223.
423. 9
378. 9
079. 7
223,
14.
14.
238,
product of combustion in the case
of the
97.
IODINE COMPOUNDS
("Methyl iodide (v)
\Methyl iodide (liq.).

Methylene iodide
CH2I2
CHI3
Iodoform
C2H4I2
Tetraiodoethylene
C2I4-
._
(s)
C3H7I
C3H5I
Isopropvl iodide ..
.
Allyl iodide
_.
TetraiodopjTrol (s) (lodol)..
.
C4HNI4
C 6 H 5I
CeHcNI
Iodoaniline.
C7H5O2I
C7H5O3I
o-Iodobenzoic acid
C7H4O3I"
(s)
lodosalicylic acid (s)

Diiodosalicylic acid (s)
142.0
200. 5
268.0
394.0
194.7
178.4
161.9
156.0
357. 8
282.0
534.0
170.0
356.0
324.8
261.6
514.3
.-
..
/Ethyl iodide (v)

\Ethyl iodide (liq.)
Ethylene iodide (s)_._
C2H5I
C3H7I.
(s)_
.-
67
170.0
168.
571.0
264.0
225.0
248.0
254.0
390.0
838.5
814.8
746.6
677. 6
223.
21.
21.
21.
496.
1, 489.
1, 359.
1, 094.
2, 152.
3
9
223.
21.
21.
21.
509.1
478.3
503.1
770.7
2, 130.
810. 7
3,
769.6
706.4
699.9
3,
1,
2,
2,
3,
2,
2,
8
3
001. 7
105. 5
225. 4
21.
21.
21.
21.
392. 8
220. 8
958. 3
929.
170.
21.
21.
21.
67 It is
claimed that all the iodo compounds give upon combustion iodine and only inappreciable amounts
HI or HIO3. Under the conditions of the experiments solid iodine is always the end product. Individual determinations do not agree better than 0.5 to 1.0 per cent.
of
420
Bureau
Vol. 2

VIII.
4.
SULPHUR COMPOUNDS
98.
68
Kg-cahsl
NumMolec-
Name
Formula
ber
ular
of
Kg-cali5
(experi-
weight
elec-
mental)
Kilojoules
(K.
(calcu-
lated to
J.)
trons
Carbonyl sulphide
{Carbon disulphide
COS..
cs 2 ...
CH
(g)_-.
(v)._
60.0
76.0
Carbon disulphide (liq.)_

Methyl mercaptan (v) . _
76.0
CH4N2S.
48.0
Thiourea (s)
Ethyl mercaptan (v)._.
(Ethyl mercaptan (liq.).
76.0
62.0
62.0
CjH 6 S__
Dimethyl sulphide
C2H6S.
(Methyl thiocyanate
(Methyl thiocyanate
(v)
(liq.)__.
isothiocyanate (v)
C2H3NSC2H3NS.
Taurine
C3H5NS.
C3H5NS-
Ethyl thiocyanate
Ethyl isothiocyanate (ethyl
mustard oil).
Thiohydantoic acid (s)
Thiohydantoine (s)
C 3 H602N2S__..
C3H4ON2S
(s)
(Diethyl sulphide (v)

(Diethyl sulphide (liq.)
C4H10S...
Dimethyl N-methylcarbimidodithiolate "

S-Methyl N-dimethyldithiocarbamate (sol.). 72
Methyl formothialdine 73 ._.
C4H9NS2-
C4H9NS2C4N9NS2C4H8N2S.
4
73.0
Methyl
(Methyl mustard oil).
Methyl isothiocyanate (v)
Methyl isothiocyanate (s).
C2H7O3NS.
7"
Thiosinamine (s)
(Ally! mustard oil
(Allyl mustard oil
Thiophene
Thiophene (v)
H x\T S_
5
C4H4S._.
1,
394.5
297.6
1,
CisHioN2S2
Dimethyl
C5H10N2S2C5H10N2S2-
Carbothialdine (sol.) "

Pentamethylenediamine
dithiocarbamate. lb
formocarbothialdine (sol.). 76
di-
1,
077. 7
032.
650. 9
244. 6
223.
223.
13.
17.
223.
342. 8
1,
452.0
517.2
434. 6
890. 3
164. 5
130.
223.
2,
1,
905.
223.
397.4
453.1
390.5
1,
1,
661. 9
896. 2
633.
223.
20.
1,
1,
22.
223.
20.
442.9
1,
853. 5
382.9
1,
602. 4
17.
87.0
87.0
613.8
604.1
2,
568. 8
2, 528. 2
20.
134.0
116.1
498.5
503.0
2,
90.0
3, 216.
103.0
769.2
829.5
969.2
4,
056.
61.
103.0
953.9
3,
992.
61.
103.0
964.5
4,
036.
116.0
99.0
791.8
732.5
672.8
670.5
608.2
3,
84.0
Dimethyl N-ethylcarbimide
dithiolate. "
S-Ethyl ester N-dimethyl-
sulfine (sol.).
1,
246. 6
125.0
(v).
C5H11NS2-
C5H11NS2.
545.8
130.5
257.7
62.0
(v)
Literature
state)
C9
4 S.
the
liquid
20.
086. 2
105.
130.
8
3,471.5
223.
2,
313.
3, 065.
2, 813.
2, 806.
2, 543.
130.
22.
61.
7
5
20.
20.
223.
37.
223.
117.0
1,
130.
4,
729. 5
61.
117.0
1,
122.
4,
695. 6
61.
130
1,
098. 4
4, 596.
61.
130.0
130.0
1,
085. 8
4, 544.
1,112.7
4,
656. 7
78
w The data
of (223) refer to the formation of gaseous SO2.

All other values, unless otherwise indicated,
refer to the production of a dilute solution of sulphuric acid.
Cf. the recent paper of A. Mennucci, Rev
faeultad. cienc. quim., 2, p. 25; 1924. This author states that complete oxidation of sulphur derivatives
to SO3 does not occur even at 25 atm. with an evolution of 10,000 calories of heat. The results of the different investigators are not comparable and can not be brought to a comparable basis, for the amount of
water used in the bombs is not in all cases specified. In view of the relatively large error that
thus be
may
introduced, all molecular weights are given in round numbers, and no vacuum or other corrections have
been applied to the values of any investigator except that the usual correction has been applied to work of
(223).
69
Gaseous SO 2.
Bomb
contained exactly 25 cm3
CH3.N = C=(SCH ) 2
72(CH 3 ) 2 NC-S-SCH3.
71
/S-CH2X
X S-CH2 X>NCH
73H 2 C<
3.
C H N = C (SCH
"(CH3) N-C<f_ C2H5CS (CH = N-CH
H
77CS (CH C=NH)
/SCHk
H C<N
>NCH N = CH
SCH /
2
3) 2 .
76
7s
3) 2 .
2.
'
2.
0.
Final state of
H2SO4 corresponds
to
H2SO4. 200 H2O.
421
Kharasch]
4.

98.
SULPHUR COMPOUNDS Continued

Kg-calis
Num-
Name
Formula
Molec-
ber
Kg-calis
Kilo-
ular
of
elec-
(experi-
joules
mental)
(K.
weight
(calcu-
lated to
J.)
trons
C5H8O2S
Tetrahydro - a - thiophene-
C5H4O2S
a-Thiophenecarboxylic acid
C6H13NP2
C6H13NS2
Thialdine (sol) "

Diethyl N-methylcarbimi-
CeHwNSa
S-Methyl N-diethyldithiocarbamate. si
131.0
C6H12O4N2S2---
Cystine
C7H5NS
Phenyl mustard oil. ______

Dimethyl N-phenylcarbim-
carboxylic acid
the
Literature
liquid
state)
130.2
754.8
3, 156.
128.0
646.2
2,
5,
1,
263. 6
289. 4
1,
271.
5,
240. 25
82
993.
4, 156.
135.0
165.0
1,024.3
544. 5
4, 286.
22.
1,
6,
463. 7
61.
322. 20
2, 278.
9, 533.
185.
(s)
702. 4
185.
(s).
dedithiolate.
C9H11NS2.
(s)
idedithiolate
1,
288. 2
5, 396.
61.
322.
61.
...
(sol.).
_____
>NH
H X CH
CH N = C
so
thia-
3.
(SC2H5)!.
S
H NC^
si
(C 2
82
Gaseous SO2.
5 )2
SCH
3.
C 6 H 5 N = C (SCH3) a
83
IX.
1.
2.
3.
4.
5.
6.
7.
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83
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H /CH3.
H/S-C<
'<>H3C.C<
61.
so
OMH14O2N2S... Benzonaphthoquinone
zine
131.0
131.0
178.
422
Bureau
25. Berthelot
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34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
54.
55.
56.
57.
58.
59.
60.
61.
62.
[voi.is

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Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Berthelot
Vieille, Compt. rend., 102, p. 1284; 1886.
Berthelot
Vieille, Ann. chim. phys. (6), 10, p. 433; 1887.
Berthelot
Vieille, Ann. chim phys. (6), 10, p. 455; 1887.
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33.
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
and
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Emery and
65.
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66.
67.
68.
69.
70. Fries,
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U.
S.
Dept. Agri. Bur. An. Ind.
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71.
U. S. Dept. Agri. Bur. An. Ind. Bull. 124; 1910.

Garner and Abernethy, Proc. Roy. Soc. London (A), 99,
Fries,
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Genvresse, Bull. soc. chim. (3), 9, p. 219; 1893.
74. Gibson, Storrs School Agri. Exper. Sta. Bull. 6, p. 182; 1890.
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72.
73.
1923.
76.
Gottlieb, J. prakt. Ch. (2), 28, p. 385; 1883.
423
Kharasch]
Ann. chirn. phys. (8), 14, p. 311; 1908.

Compt. rend., 121, p. 354; 1895; 122, p. 943; 1896;
collected and evaluated in Ann. de Chim., 10, p. 59; 1918.
Hartmann, Proefschr. Delft; 1925.
77. Guillemard,
78. Guinchant,
79.
all
data
Henning, Z. phys. Ch., 97, p. 467; 1921.

Hibbert and Fuller, J. Am. Chem. Soc, 35, p. 978; 1913.
82. Huckei, Lieb. Ann., 451, p. 117; 1926.
83. Huckei, Lieb. Ann., 451, p. 160; 1927; Det. by Roth.
84. Jaeger and von Stein wehr, Zeit. phys. chem. 114, p. 59; 1924.
80.
81.
85. Jaeger
and von Steinwehr,
Zeit. phys.
chem., 119, p. 214; 1926.
91.
Wied. Ann., 37, p. 408; 1889.

Karrer and Fioroni, Helv. Chim. Acta, 6, p. 396; 1923.
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Konovalov, J. Chim. Phys., 33, 359; 1926.
92.
Krummacher, ZS.
86. Jahn,
87.
88.
89.
90.
93. Landrieu,
94. Landrieu,
95.
96.
97.
98.
99.
100.
101.
102.
103.
104.
105.
106.
107.
108.
Landrieu
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Lemoult,
Biol., 46, p.
Compt,. rend.. 140,
310; 1904.
p. 867; 1905.
Compt. rend., 142, p. 580; 1906.

and Blatt, Bull. Soc. Chim., 35, p. 1424; 1924.
Compt. rend., 126, p. 343; 1898.
Compt. rend., 143, p. 772; 1906.
Compt. rend., 143, p. 902; 1906.
Ann. chim. phys. (8), 10, p. 395; 1907.

Ann. chim. phys. (8), 13, p. 562; 1908.
Ann. chim.. phys. (8), 14, pp. 184, 289; 1908.
Compt. rend., 148, p. 1602; 1909.
7th Int. Cong. Appl. Chem.; 10, p. 75; 1909.
Compt. rend., 152, p. 1402; 1911.
Leroux, Compt. rend., 151, p. 384; 1910.
Leroy, Ann. chim. phys. (7), 21, p. 87; 1900.
Leroy, Compt. rend., 130, p. 508; 1900.
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mann)
Ann. chim. phys. (5), 20, p. 558; 1880.
Ann. chim. phys. (5), 21, p. 139; 1880.
Louguinine, Compt. rend., 91, p. 297; 1880.
Louguinine, Compt. rend., 101, pp. 1061, 1154; 1885.
Louguinine. Compt. rend., 106, p. 1289; 1888.
Maibot, Ann. chim. phys. (6), 18, p. 404; 1889.
Massol, Ann. chim. phys. (7), 1, p. 145; 1894.
109. Louguinine,
110. Louguinine,
111.
112.
113.
114.
115.
116.
117.
118.
119.
120.
121.
122.
123.
124.
125.
126.
127.
128.
129.
369729
424
Bureau
\voi. %
Ann. chim. phys. (6), 28, pp. 70, 289, 498; 1893. These articles
contain also the data reported by Matignon in Compt. rend., 110, p.
1267, 1890; 113, p. 198; 1891.
130.5 Matignon, Compt. rend., 113, p. 198; 1891.
131. Matignon and Deligny, Compt. rend., 121, p. 422; 1895.
132. Matignon and Deligny, Compt. rend., 125, p. 1103; 1897.
133. Meier and Meyerhof, Biochem. Z., 150, p. 233; 1924.
134. Meyerhof, Biochem. Z., 129, p. 594; 1922.
135. Meyerhof, Pfliig. Arch., 195, pp. 22, 24; 1922.
136. Mixter, Sill. J. (4), 12, p. 347; 1901.
137. Mixter, Sill. J. (4), 22, p. 13; 1906.
138. Moureu and Andre\ Ann. chim. (9), 1, p. 113; 1914.
130. Matignon,
139.
140.
141.
Moureu and Bongrand, Compt. rend.,

Moureu and Boutaric, J. chim. phys.,
Moureu, Boutaric, and Dufraisse,
Ann. chim. phys. (8), 20,
142. Muller,
J.
170, p. 1025; 1920.

18, p. 348; 1920.
chim. phys., 18, p. 333; 1921.
p. 116; 1910.
143. Muller, Bull. soc. chim. (2), 44, p. 608; 1885.

144. Ossipov, Z. physik. Ch., 2, p. 648; 1888.
Ann. chim. phys. (6), 20, p. 371; 1890.

Chim. russe, 22, p. 317; 1890.
Petit, Ann. chim. phys. (6), 18, p. 145; 1889.
Pushin, Z. physik. Chem., 124, p. 16; 1926.
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145. Ossipov,
146. Ossipov, J. de la Soc.

147.
148.
149.
150.
151.
1923.
and Barry, J. Am. Chem. Soc, 37, p. 993; 1915.

and Davis, J. Am. Chem. Soc, 39, p. 341; 1917; 42,
Richards and Jesse, J. Am. Chem. Soc, 32, p. 268; 1910.
Riiber and Schetelig, ZS. ph. Ch., 48, p. 345; 1904.
152. Richards
153. Richards
154.
155.
156.
p. 1599, 1920.
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Ann. chim. phys. (7), 12, p. 501; 1897.
Rosenhain, J. Soc chem. Ind., 25, p. 239; 1906.
Roth, Lieb. Ann., 373, p. 249; 1910.
(Value by Lemoult corr. by Roth.)
Roth, Rec trav. chim., 45, p. 248; 1926.
Roth, ZS. Elektrochem., 16, p. 654; 1910.
Roth, ZS. Elektrochem., 17, p. 789; 1911.
Roth, Unpub. work. Authority for these values in Landolt-Bornstein
157. Rivals,
158.
159.
160.
161.
162.
163.
Tabellen; 1923.
164. Roth, Landolt-Bornstein Tabellen; 1927.
Roth and v. Auwers, Lieb. Ann., 407, p. 145; 1915.

Roth and v. Auwers, Landolt-Bornstein Tabellen; 1927.
167. Roth and Ellinger, Landolt-Bornstein TabeJlen; 1923.
167.5. Roth and Ellinger, Landolt-Bornstein Tabellen; 1912.
168. Roth and Ellinger, Landolt-Bornstein Tabellen; 1927.
169. Roth and Lasse, Lieb. Ann., 441, p. 48; 1925.
170. Roth and Macheleldt, Diss. Braunschweig; 1921; quoted
165.
166.
Bornstein Tabellen; 1923.

171. Roth and Moosbrugger, Landolt-Bornstein Tabellen; 1923.
172. Roth and Muller, Landolt-Bornstein Tabellen; 1927.
173.
174.
175.
176.
177.
178.
Roth
Roth
Roth
Roth
Roth
Roth
and
and
and
and
and
and
Muller, Ber., 60, p. 643; 1927.
Murawski, Landolt-Bornstein Tabellen; 1923.
Chem. Ges., 46, p. 309; 1913.

Peters, Landolt-Bornstein Tabellen; 1923.
Ostling, Ber.
Stoermer, Ber. chem. Ges., 46, p. 260; 1913.

Wolff, Landolt-Bornstein Tabellen; 1927.
in
Landolt-
EharasM
179. Schmidlin,
425

Ann. chim. phys. (8), 7, p. 195; 1906.
Chem., 117, p. 57; 1925.
180. Schreiner, Z. physik.
181.
182.
183.
184.
185.
186.
187.
188.
189.
190.
191.
192.
193.
194.
195.
196.
197.
198.
199.
200.
201.
202.
203.
204.
205.
206.
207.
208.
209.
210.
211.
212.
213.
214.
215.
216.
217.
218.
219.
Stohmann, Journ. prakt. Ch. (2), 31, p. 273; 1885.

Stohmann, ZS. ph. Ch., 6, p. 334; 1890.
Stohmann, ZS. ph. Ch., 10, p. 410; 1892.
Stohmann and Haussmann, J. prakt. Ch. (2), 55, p. 263; 1897.
For details
consult Berichte liber die Verhandl. der kgl. Sachs. Ges. der Wissensch.
zu Leipzig, 49, p. 1; 1897.
Stohmann and Kleber, J. prakt. Ch. (2), 43, p. 1; 1891.
Stohmann, Kleber, and Langbein, J. prakt. Ch. (2), 40, p. 77; 1889.
Stohmann, Kleber, and Langbein, J. prakt. Chem. (2), 40, p. 341; 1889.
Stohmann, Kleber, Langbein, and Offenhauer, J. prakt. Ch. (2), 49, p. 99;
1894.
For details of the work consult Berichte iiber die Verhandl. der
kgl. Sachs. Ges. der Wissensch. zu Leipzig, 45, p. 604; 1893.
Stohmann and Langbein, J. prakt. Ch., 42, p. 361; 1890.
Stohmann and Langbein, J. prakt. Ch., 44, p. 336; 1891.
Stohmann and Langbein, J. prakt. Ch. (2), 45, p. 305; 1892.
Stohmann and Langbein, J. prakt. Ch. (2), 46, p. 530; 1893. For details
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Stohmann and Langbein, J. prakt. Ch. (2), 48, p. 447; 1893.
consult Berichte iiber die Verhandl. der kgl. Sachs. Ges. der Wissensch. zu
Leipzig, 49, p. 1; 1897.
consult Berichte iiber die Verhandl. der kgl. Sachs. Ges. der Wissensch. zu
Leipzig, 49, p. 1; 1897.
Stohmann, Rodatz, and Herzberg, J. prakt. Ch. (2), 33, p. 241; 1886.
Stohmann, J. prakt. Ch. (2) 35, pp. 40, 136; 1887.
Stohmann and Schmidt, J. prakt. Ch. (2), 50, p. 385; 1894.
Stohmann and Schmidt, J. prakt. Ch. (2), 52, p. 59; 1895. For details
consult Berichte iiber die Verhandl. der kgl. Sachs. Ges. der Wissensch.
zu Leipzig, 47, p. 1; 1895.
Stohmann and Schmidt, J. prakt. Ch. (2), 53, p. 345; 1896.
Swarts, Bull Acad. Belg., 14; 1924.
Swarts, Rec. Trav. Chim. Pays Bas, 32, p. 59; 1913; J. chim. phys.,
17, p. 3; 1919.
Swietoslawski, ZS. ph. ch., 72, p. 49; 1910.
Swietoslawski, J. Russ. Phys. Chem. Soc, 46, p. 1302; 1914.
Swietoslawski, J. Am. Chem. Soc, 39, p. 2595; 1917.
Swietoslaswki, J. Am. Chem. Soc, 42, p. 1092; 1920.
Swietoslawski, J. chim. phys., 22, p, 583; 1925.
Swietoslawski, Private comm.
Swietoslawski and Pakovick, J. Russ. Phys. Chem. Soc, 46, p. 1284; 1914.
Swietoslawski and Popov, J. Russ. Phys. Chem. Soc, 46, p. 935; 1914.
;
220. Swietoslawski,
Popov, and Pakovick,
J.
Russ.
Phys.
Chem. Soc,
p. 1293; 1914.
221. Swietoslawski
and Starczewska,
Bull. soc. chim. (4), 31, p. 654; 1922.
46,
426
Bureau
Vol. 2
and Starczewska, J. chim. phys., 22, p. 399; 1925.

Thomsen, Thermoch. Unters. IV: letzte Zusammenstellung; ZS. ph. Ch.,
222. Swietoslawski
223.
52, p. 343; 1905.

224. Tower, Value reported
p. 608;
by Atwater and
Snell,
J.
Am. Chem. Soc,
25,
1903.
Ann. chim. phys. (7), 21, p. 470; 1900.

226. Verkade, Amst. Akad. Versl., 35, p. 496; 1926.
225. Valeur,
Values by Verkade, van de

Lee and Coops.
227. Verkade, Proefschr. Delft; 1915.
228. Verkade, Chem. Weekbl., 19, p. 389; 1922.
229. Verkade and Coops, Rec. Tr. Chim. P. B., 45, p. 551; 1926.
230. Verkade and Coops, Rec. Trav. Chim. P. B., 43, p. 561; 1924.
230.5. Verkade and Coops, Rec. Trav. Chim, 42, p. 223; 1923.
231. Verkade and Coops, Private comm.
232. Verkade, Coops and Hartmann, Rec. Trav. Chim. P. B., 41, p. 241; 1922.
233. Verkade, Hartmann and Coops, Rec. Tr. Chim. P. B., 45, p. 585; 1926.
234. Verkade and Hartmann, Priv. comm.
235. Verkade, Hartmann and Coops, Proc. Acad. Sc. Amsterdam, 2?, p. 859;
1924.
236. Verkade,
Verkade and Coops, Landolt-Bornstein Tabellen; 1927.

and Maan, Priv. comm.
237. Verkade, Verkade, Coops,
238. Voisenet, Bull. soc. chim. (4), 17, p. 34; 1915.

239. Wartenberg, Muchlinski, and Riedler, Z. Angew. Chem., 37, p. 457; 1924.
240. Weigert, ZS. phys. Ch., 63, p. 458; 1908.
241. Wrede, ZS. phys. Ch., 75, p. 81; 1910.
242. Wrede, Landolt-Bornstein Tabellen; 1927.
Russ. Phys. Chem. Soc. (7), 28, p. 687; 1896.

Russ. Chem. Phys. Soc, (7), 30, p. 926; 1898.
245. Zubov and Swietoslawski, Bull. Soc. Chim., 37, p. 271; 1925.
246. Bureau of Standards, Unpublished work.
243. Zubov,
J.
244. Zubov,
J.
X.
INDEX OF COMPOUNDS, BY FORMULA

CH COMPOUNDS
1.
Formula
CH
C2 C2H2
C2H 4 _
C2H6
C3H4
C He
CH
3
373
376
373
374, 376
C^HsC4H10
C5H10
C5H12
CeHo
CeHg
C 6 Hi2
CeHu
C H8
7
C7H12-
C7H14
C7H16
8
CgHio-..
CsHi2
CgHii
C9H10-
C9H12
C9H16
C9H18
C10 CioHs
C10H10
G10H12--
CioHu
C10H10
373
375
374, 377, 378
374
373
376, 378
375
377
377, 378
C9H14
373
378
CsHs-
C8 CsHi6
C8H18
375, 378
377
374, 376, 377
374, 376
CeHio
C CH
373
378
376
373
378
374, 376
Formula
Page
374, 376
C12 C14H12
373
376
375
378
C14H28
C15H14
378
374
375
378
376, 377, 378
Cl6Hl4._.
C16H34
C18H12--CisHie
CisHis...
375, 378
C18H20
C19H15
C19H16--C20H16
378
374, 378
374, 376
C10H20
C10H22
Page
.-
377
375
374
377
378
377
373
376
377
376, 377
--
377
375
375
377
373
ChHh-.
CnHis
C12 C10H10
C12H1S
C12H24
C13H10--C13H12
ChHio
Formula
Page
377
375
378
375
377
375
376
376
375
376
C24H 18
C25H20
373
376
375
376
KharascJi]
INDEX OF COMPOUNDS, BY FORMULAContinued

2. CHO COMPOUNDS
X.
Formula
Ci
CH
Formula
Page
384
|(CH 2 0)n
384
CH2O2
C2 C2H2O2
380
386
382
382
382
C 9 H 02
CeH 6 03
6
379, 384
384, 399
CeHsOe
C2H2O3.H2O.__
C2H2O4
C0E4O
C2H4O2
C2H4O3
2
C3H4O4
C3H4O5
C3H4O6
C3H6OC3H6O2-
392
392
382, 385, 387
Page
Cs C8H8O2
CsHsOs
393, 394, 400

385, 393, 394,
CsHsOi
CsHsOs
CsHioO
..
C8H10O2
C8H10O3C8H10O4
379, 385
C 8 Hio02
382, 385, 390,
390
390
C6H10O3
398, 401
383
398
C 8 Hi 2
387
C6H10O4
391
392
392
379, 384, 385
C 8 H U 02
402
388, 399
389
399, 400
392
(C 6 Hio0 5 )x
CeHioOe
CeHioOs
401
398
397, 400, 401
379, 380, 387
381, 397
CsHhO..
383, 391, 400,
C Hio0 5
383, 389, 399,
390, 397, 401
C8H12O3
C8H12O4
399
CsHuOs
402
C8H14O4
383, 391, 400,
C Hi
8
402
392, 402
399
379,380,386
06
CsHÔs
CsHieO
C Hi60 2
C Hi
381, 389
379, 380
C3H6O3
H 0___
C3H8O2
C H 03-__
C
CcHi 2
390, 400
379, 382
380, 383
C4 C4H2O3--
380
397
C4H2O4
C4H4O2
C4H1O3
C4H4O4
C4HeO___
393
390
397
393
382, 385
__
C6H12O2
C Hi
6
C4HsO_
C4H8O2
C6H14O2
C6H14O6
_.
02-
C H603-C H 04
5
C5H80.
c 5H 8 o 2
C 5 H 8 03
C5H804
C5H807-C5H10O
380
385
390, 397
401
-_-
C7H10O2
C7H10O3
382
396
398
C7HioOi
393, 396, 399,
C7H10O5
400
400
379, 380, 385,
403
390, 399
C7H14O2
381, 389, 401,
391. 400
C7H14O8
C7H14O7
401
396
399
385, 390, 396,
401, 402
385
394
395
0e
379, 384, 385,
387
C9H8O2
C9H8O3
394, 402
393, 394
8
S 04
C9H10O2
381, 393, 394,
C9H10O3
402
400, 402
395
386
403
-_
383
388
379, 380
383
381
_.__
398
399
385
394, 395
386
C HicO
7
C7H16O2
C7H16O7
C9H12OC9H12O3
C9H14O
C9H14O2
C9H14O4
386, 387
390, 397, 399
381, 400
C9H14O3
C9H14O7
C9H16O
C 9 1C 04
CgHisO
379, 380, 387

391, 400
379, 380
382, 383
385
396
C7H14O
OsHioOs
C5H10O5
CoHsO
379, 382, 383
391, 400, 402
379, 381, 389,

399, 401
394
394
394
C7H12O4
C7H12O6
C7H12O7
C5H10O2
C9H6O2
385, 386, 393
382, 396, 401
392
379, 384, 385
380, 388
379, 380
380, 382, 383
C7H12O2
C7H12O3
387
C CH
385
02
6 03
6
C 7 H 12
393, 396
H
H
C7H608
C7H80..
C7H802
397
C7H604
C7H805
380, 383
C5H4O3-
C
C
385
381, 389, 401
385
380, 388
388
381
397
C7H4O7
C7H6O
401
390, 399
379, 380, 382
383
C4H10O3
C4H10O4
C CH
382, 385
385, 389, 399,
C4H8O3-C4H10OC4H10O2
C Hi40
397
391, 400
392
392
_
CeHsOe
383, 385, 390,

396, 403
C4H6O3
C4H6O4
C4H6O5
C4H6O6-
C6H12O5
C6H12O5.H26.__
C
C4H6O2
379, 380, 384,
383
400
C9H18O2-
389
380
383
386
386
C9H20O
C9H20O2
i0
CioH 6 2
CioH 6 04CioHcOs
CioHsO
CioH 8 2
CioHgOs
C10H8O4
._
C5H12O
C5H12O2C5H12O..
C H602
400
398
386, 394, 396
C10H10O
C10H10O2
C10H10O3
C10H10O4
C10H10O5
CsHeOs
C
C
H 04
H
6
8
C 10 Hi O
2
C10H12O2
C10H12O3 CioH 12 4
395
382, 386
386
383, 394, 400
395
396, 399, 401
394
CioHioOe
388
379, 380
383
380
C C H-0
400
397
400
382, 383
397, 402
C8H12O2
380
CeHsO?
C6H8O7.H2O
C 8 HioO
379, 382
C2H8O2--C3 C3H4O
C3H4O2
C3H4O0
C6H8O4
CeHsOe
393
390
398
393, 396, 400
391
C 6 H80 2 -C H 03
390
391
384, 385
389, 399
390
Formula
Page
C5 C5H12O5.
C 6 C6H4O2
CeHeO...
389
CH4O
427
__
_-
394
383
381, 383, 386,
393, 403
403
400
428
Bureau
Formula
382, 383, 387
C10H14O2-.
C10H14O3..
382
398
400
401
C10H14O4CioHuOs..
CioHieO...
CioHwOa..
CioHicOsC10H16O4..
CioHi 8 0.
C10H18O2C10H18O4C10H20O-..
C10H20O2-C10H22O...
C10H22O3C11H8O2-.
C12 Ci 2 His08~
C12H20O2-
385, 387
390, 397, 399,
402
397, 398
381, 397, 401
379, 380
397
392, 400, 402
379, 380
OuHioOj..
395. 402
395
C11H12O..
386
395
399
383. 403
403
CuHhOsCnHieO..
C11H16O2-.
C11H16O4-.
C18H32O2-.
C12H22O2
C12H22O3C12H22O4
398
400
C18H32O18-C18H32O16H2CLC18H32O16.5H2O
C13H10O2C13H12O..
C13H14O..
C13H14O4-
C,4
381
395
C13H16O8..
C13H20O...
386, 387
C13H24O2C13H24O4-
383
392
Cl4H 8
14
6.
ChHsOs.
Ci4H 10 O 2 C14H10O3C14H10O4.
C14H12O2C14H12O3-
386
387
387
387
C14H12O4-
ChHisO..
403
381
386
381
379
380
389
383
398
395
C14H18O3C14H20O8C14H22O8.
C14H26O3C14H28O2-
395
402
402
398
389
395
400
C15 C15H10O..
C11H2202-.
40 2 -.
C12 C12H6O3-,
Ci 2 6 0i2-.
2
C12H8O4-.
C12H10O2..
Ci2H 10 O 4 -.
C12H12O...
C12H12O3-.
C12H12O6-
C15H14O2C15H20O6C15H26O6-
386,!
386
395
Cie
C16H12O3C16H14O4C16H16O2Cl 6 2 20n
C16H3202-
C12H12O12.
401
397
C12H14O2Cl2Hi40 3 -.
402, 403
395, 400, 402,
C12H14O4-.
403
384
Ci2Hia0 2 -
381, 384, 403
C17 C17H14O..
C12H16O3-.
C 12 Hi80...
C12H18O2-.
384
384
402
C17H1603C17H1802-
Cis
403
403
403
C 16 Hio0 3 .
C 16 H
3i
C21H18O2C21H22O4-
O..
CisHhOs.
C22
C22H13OC22H40O2C22H42O2C22H44O2C22H 44 04-
Ci 4 16 0..
C14H16O4.
C11H220..
C20E20O4C20H22O4C20BU0O2C21 C21H16O-.
C 2 iHi60 2 -
C23 C23H18O4C 2 3H 2 oO_.

C24 C24H20O4.
401
390
392, 400
2.
02.
386
,395,403
395
401
16
382, 386
385, 398
390, 402
399, 402
Ci4H 14
C19H16O..
C19H18O4C19H20O5C19H36O4C20 C20H14O4.
2.
C14H8O3.
C14H8O4-
401
384
402
401
386
403
379
386
CnHieOs-.
C11H20O4-.
C18H34O2
C18H36O2 .
C19 Ci 9
C12H24O2C13 C13H10O-.
C11H18O2-.
C11H18O3-.
C11H18O4-.
CnH20O2-.
Ci 8 Hi<s04-.
CisHisOn.
C18H23O6-
Cl2H220 U .H 2
380
C 18 H 16 02..
C12H20O6C12H20O7-
C12H22O11
389
382
C11H10O4-,
Cis
403
398
383
402
C12H20O3-.
CuHioO..
C11H12O3-,
C11H12O5-,
C11H14O2-.
C11H14O3-.
Formula
Formula
Page
Cio C10H14O...
CnH
INDEX OF COMPOUNDS, BY FORMULA Continued

X.
Cn
398
396
384, 395, 403
388
379
386
395, 403
403
398
C24H20O6C24H20O8C24H22O...
C24H42O21-
C27+C27H460.
C28H22O3
C28H38O19.
C32H30O3C32H64O2C39H74O6C45H86O6C47H 8 80 5 ..
C48H380l2Ce9Hl2806-
vol.

3. N COMPOUNDS
X.
Formula
CH NO...
3
CH3NO2CH4N2O..
CH
429
Kharasch]
N___.
CH0N4O3.
Formula
Page
406
411
406
404
406
Co
Formula
Page
C5H5N....
5 N 5 0.
C 5H
C5H6N2-.
C5H6N2O2
C5H6N2O3
410
408
408
C7
C7H15N
C7H17N
CsHsNO....
C8H5NO2---
404
404
C 8 H N204
C H 6 Na03.
2H
C 8H N
B
C2
C2N2
C2H3N-..
C2H3NO.
C2H3NO3C2H4N2O2-
C2H5NO-C2H5NO2C2H5NO3-
C2H6N2O
C2H6N2O2
C2H7N
C2H8N2.H2O.
C C3H2N2
3
C3H2N2O3-.
C3H 3 N 2 Ag.
C5H6N4O4-.
C3H5N
C3H5NO...
C3H5NO3-.
C3H5N3O9C3H6N2O2C3H6N2O3C3H7N.-.
C3H7NO..
C3H7NO2-,
C3H7NO3C3H8N2O-3
HN
9
C4N2
C4H2N2O4.
H
C H N2..
C4H4N2O3C HN
4
C4H5NO2--
C4H 5 N 2 Ag.
C4H5N3
C4H7N
C4H7NO3-.
C4H7NO4-.
C4H7N3O-.
C4H8N2O2C4H8N2O3.
C 5 HgN
405,411,415
415
C4H9NO-C4H9NO2C4H9NO6C4H9N3O2C4H9N2O2.
C HuN....
4
C5H4N4O,.
C5H4N4O2C6H4N4O3-
C5H9N
C 5 H 9 N04-
C5H11NO..
C0H11NO2-
CsHnNOe-
108
Ca
406
C6H3N3O6C6H3N3O7C6H4N2O4C6H4N2O5-
C8H10N4O2C 8 HiiClN 2
CaHuN
C8H12N2O3CsHisNO...
C 8 Hi 4 N40 5 ..
CiHuNiOt-.
C8H16N2O4-
404
411
412
411,414
412
CsHigN
CeHeNi...
408. 410
C9H9N
408
405, 408
405. 411
410
C9H9NO3---
C6H7NO..
C 6 H 7 N03.
8 H 8 N2
C6H9NO2-C6H9NO4-.
CeHgNOe-C 6 H9N 2 Ag.
C6H10N2O2CeHiiN....
C 6 H U N304.
C6H12N2O3C 6 Hi2N4...
410
410
C C9H5N
9
C9H7N
C9H7NO....
C9H10N2O4--
C9H11N
CoHuNO...
C9H11NO2
C9H11NO3
CH 13 N
405, 415
410
409
406
410
406
410
406
406
CeHwNOa.
C 6 Hi 8 N._.
08
C7H5N-
C 7 H 6 N03.
C7H5NO4-.
C7H5N3O6C7H5N5O8C7H6N2O4C7H6N4O3CrHTNO...
C7H7NO2-.
C7H7N3O4C7H8N2O-.
C7H8N2O2C7H8N4O2C7H9N-...
C7H9NO..
C7H9NO3.
C7H10N2....
C7H u 2 Ag....
C7H13NO3...
C7H14N2O2-
408
407
406
406
407
409
404
410
409
407, 410
413
409
407
412
408
407
406, 412
406
404, 405
407
C9H16N2O5-
406
413
414
408
405, 409
C10H7NO2...
C10
405, 410
C9H10NO..-
C9H17NO
CioHsNsOaC10H9N
C10H9NO4
C6H13NO2-
406
407
407,413
415
392
407
0._.
C6H5N3O3C 6 H 6 N202CeHjNaOs.
C6H7N....
410
408
408,410
409, 410
407
411,414
412
415
412
411
C 6 H 8 N40.
408
404
410
407
406
406
412
414
408
414
C9H7NO4...
406
404
406, 413
405,406,411
405
407
406
CsHoNOj.
C6H5NO2C6H5NO3-
406
415
406
108
410
412
412
408
407, 414
C Hi
409. 410
409. 411
408
408. 410
C8H7N5O8
CgHsNaOs
CsHgNeOe
C 8 H 9 NO..
C HioN
407
404, 408
407
406
392
410
CbHuN
412
C8H7NO2
CsHgNOs
C5H10N2O2C5H11N....
410
408. 409
410
409
410
406
408
410
406
05-
C5H8N4O3-
414
414
404
404
409
C4H8N2O3.
C4H8N2O4-
C5H8N2O2-
C4H5N3O3-.
C4H6N2O2-.
C4H6N4O3..
N Ag.
C5H7N5O3-
406
406
2 02-.
C3H4N2O4-.
C 5H
406, 413
C3H3NO2-.
C3H4N2O-.
C H4N
C5H7NO2-.
C5H7NO4--
409. 410
409. 411
Page
C10H11NO3C10H11NO4-
392
404
410
413
C10H13N....
C10H13NO2CioHisNOaC10H14N2
413
412
C10H15N
C10H15NO3-
412
412
412
C10H17NO
C10H19N.-..
C10H19N3O4C10H23N
407, 414
412
412
407
412
Cn C11H7N
C11H11NO4C11H13NO3-
CnHuNO.404,405,408
405
410
415
410
406
407
CnHisNOeC12
C12H9N
C12H10N2-
C12H10N2OC18H11N....
G12H11N3.
G12H12N2
407
407
409
407, 414
392
405
411
413
404
406
404
410
409
407
410
392
409
414
414, 415
405
414
405, 415
430
Bureau
of Standards Journal of Besearch
[Vol.

X.
Formula
Cl2 C12H12N4
C12H14N4O6
C12H14N4O8
C12H22N2Q2C12H27N
C13
C13H11NO
C14H14N2O2C14H15N
C14H16N4O
C 15 H
13
414
408
408
406
404
Cie C1GH10N2O2
C16H11NO2
OigHuNOs
407
412
414
404
C16H1SN2O2
C16H1SN2O3-
H7Br___.
C17H19NO3H2O
C19H21NO3 . -
CH3CI2.
CH3CI
C6H3CI3O2-CGH4CI2
419
419
419
C6H4CI2O2-
C8H5CIO2
C H4Cl20._.
C H CIO_._
C7H5CIO2
7
2 C2OI4
C2CI.
C2HC1302C2H2C13NC
C2H3CL
C2H3CIO..
C3H3CI02-.
C2H4C1NO
C2H4C12
C2K5CL--.
3 C3H4CI2
C3H5CL...
C3H6OI2
418
418
418
418
418
418
418
419
418
418
418
419
C7H7CI
C8H4CI2O2Cs
C4H6C12O2-
C4H7CIO2C4H9OI....
CeCliOs-...
CeCls
C6HCI3O2C6H2CI2O2.
C6H2CI2O4.
C6H2CI4O2.
419
419
418
419
419
COS
CS2
CH4N2S
418
418
418
418
418
CioHuCla
CisHnCL...
OmHisOL...
CH4S-...
C2
C2H3NS
C2H6S...
C2H7N03S...
C3H4N20S
C23H2BN2O4.
409
409
412
404
409
409
409
C23H.27NO8.
2H2O-.
409
Cg C 6 H 5 FO._.
C 6 HoFN_._.
C7H4F3NO2
C7H8F3----
C7H5FO2
C7H5F3O
C7H0F2
C7H7F
C7H15F.-...
Cs
2 C2H2F2O2--
C2H3F2NO..
C2H3FO2-
C2H4FNO..
C2H.5FO.-_.
C4H7F4N...
5
C C6H3FN2O46
C0H3F2NO2-
C H F2
C6H4FNO2C6H4FNO3CgH 5 F
6
CSH5FN2O2-
C9H9FO2
C HnF..__
9
O10H9FO2
I
CHI3
GH2I2
CH3I,
C2I4
C2H4I2
C2H5I
C3H5I
C3H7I
C4HI4N....
CaHjI
GgHgIN....
G7H5IO2---
C7H5IO3-C7H4I2O3
COMPOUNDS
C3H5NS
02_-
C8K17F
C9H7FO2--.
415
417
417
415
417
C9H8F3NO-
417
418
416
417
417
C4H7FO2
C H9FO.._.
CgHgFO..-
417
415
417
415
416
C2H5F2N---
CgHsFNiOs,
416
416
416
416
C2H4F2O
CgHaFNO-
418
C2H4F2N2O2.
C8H7FN3O3
C8H7F2NO-
418
419
419
419
419
420
420
420
420
420
420
420
420
C21H22N2O2
C22E23NO7
418
418
418
418
418
C H7C10_..,
C9H9CIO2
5.
Ci
C21H13NO5
C21H21N
411
411
405
409
C10 G10H17CL...
418
418
418
418
418
418
418
418
418
419
C20H21NO4
C_oHNO u _--
414
415
409
405
409
C4 OiHeFaOa
C3H7OL...
C20
Page
HALOGEN COMPOUNDS
CHCI3
15
CioHiaNsOsC19H13N3O7
Ci9HisN 3 0._.._
1
Ci CCI2-
H N
C1SH21NO3H2O
C C HsC102
Br
CH Br_._
C H Br....
C
CjoHusNOa
C16H15NO3
C16H15N2O2
415
404
409
407
412
4.
408
405
407
407
407
Ci 6 Hi 3 N_.
Cis Ci 8
Formula
Page
Cia C16H12N2O4
407, 414
C13H12N2O
Cm ChH 9 N04
Formula
Page
C3H0N2O2S....
C4H4S
C4H5NS
C4H8N2S
C4H9NS2C4H10S.
C5H4O2S_.__._-
00
420
420
420
420
420
420
420
421
C 6H
8 02S.
C5H10N2S2
C H,iNS 2 _
5
C6
CaHwN'OiSa...
C6H13NS2
C7H5NS
C9H11NS2
Cl8Hl4N 2 02S_
421
420
420
421
421
421
421
421

NIST Heat Combution Data Book

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RP41

HEATS OF COMBUSTION OF ORGANIC COMPOUNDS

The comparison demonstrates that the calculated values are sufficiently

Halogen and sulphur compounds

VIII. Tables of data

In the present collection of the data od the heats of combustion of

organic compounds, an attempt has been

difficult because only a few authors give the necessary information

The thermochemical data recorded in the tables have been obtained

Bureau of Standards Journal

" universal-burner " method, in the hands of Thomsen, gave

to the design of his apparatus,

to substances easily volatile at

applicable only to gases or

room temperature, and

his values are

be trusted only to the extent to which this condition was realized.

agree within the limits of experimental error. 4

Andrews, Pogg. Ann.,

75, p. 27; 1848.

The other two methods are those of Hosehus and

11, p. 243; 1915;

Schlapfer and Fioroni, Helv. chim. Acta,

Heats of Combustion of Organic Compounds

of calibrating the calorimetric

The methods which have been

the investigators and pertain to the values recorded are as follows:

the additive calibration.

of energy to the calorimeter and measuring the

In the additive-calibration method the heat capacity of the

thus usually impossible to compare the

values with those of other workers.

Louguinine, Zubov, and a number

been put upon a better basis by Swietoslawski, to whom Zubov

most important references dealing with the calibration

Bestimmung des Wasserwertes eines Berthelot'schen Kalorimeter in elektrischen Einheiten, W.

accurate Calorimeter, White, Phys. Rev., 25, p. 137; 1907.

of Standards Journal of Research

employed by Swietoslawski in correcting Zubov's data, it is evident

STANDARDS FOR COMBUSTION CALORIMETRY

Of the three substances which have been used

in the past as stand-

ards in combustion calorimetry, only one has been

meet the requirements

the third conference of the International

Chemistry held at Lyons, 6 benzoic acid was adopted as the primary

These ratios are quite similar to those obtained by Dickinson and

represented at that conference.

Bull. Bur. of Standards, 11, p. 243; 1915.

Heats of Combustion of Organic Compounds

for salicylic acid

absolute joules, respectively.

Since in the tables below only one value

is as a rule given for each

of procedure, corrections used, etc., or

who merely recorded the

quoted, irrespective of whether or not the value is very reliable, it

On the whole, for the guidance of the users of the tables,

ABBREVIATIONS, UNITS, AND CONVENTIONS

absolute kilo joules

of combustion recorded are expressed

weight of substance in vacuo. Where the investigators indicated the

of Standards Journal of Research

However, it was felt