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)] (2)
where
0
is initial conductivity of solution,
t
conductivity after time t and
conductivity after reaction is completed. Rearranging (2) we obtain
12
t
=(1/ak)[(
0
-
t
)/t] +
(3)
The rate constant k can then be calculated from the known initial concentration of
reactants a and a plot of
t
vs. (
0
-
t
)/t.
Experiment:
The solutions required are: 500 ml of 0.02M NaOH, 500 ml of 0.02M EtOAc (freshly
prepared) and 100 ml of 0.01M NaOAc made by neutralizing 20 ml of 0.05M NaOH with
20 ml of 0.05M CH
3
COOH and making up to 100 ml.
All solutions should be prepared with CO
2
free water. For that purpose boil 2l of
deionized water, in separate 1l beakers, cover the beaker and let the water cool to room
temperature.
All solutions should be stoppered to avoid evaporation.
Fill a 500 ml volumetric flask 3/4 full with boiled water, pipet the necessary volume of
EtOAc into the flask and make to volume with boiled water (Overall EtOAc
concentration should be 0.02M).
Clean dip-type conductivity cell with deionized water and allow it to dry. Then measure
conductivities at 30 C for the 0.01M NaOH solution (
0
) and 0.01M CH
3
COONa
solution (
).
Suspend two large boiling tubes in the thermostat at 30
C, one containing 70 ml of
0.02M NaOH and the other 70 ml of 0.02M EtOAc.
Allow the flasks to reach equilibrium temperature (10 min) and in the meantime clean
and dry the conductivity cell. Then mix the two solutions quickly and start the stop-clock.
Dip the conductivity cell in the mixture and take conductivity readings at 2, 3, 4, 5, 6, 7,
9, 11, 13, 15, 18, 20, 25, 30, 35 and 40 min after commencement of the experiment.
Repeat the experiment at 45 C and 60 C remembering to set the temperature switch
on the conductometer accordingly.
13
Data analysis:
Obtain linear least-squares fit of
t
vs. (
0
-
t
)/t and from its coefficients determine
approximate rate constant for the hydrolysis (k) and
o o
X K
e
K
= (eq. 4)
I
(hkl)o
= intensity of reflection of hkl in phase o
K
e
= experimental constant
K
(hkl)o
= structural factor for phase o
X
o
= weight fraction of phase o
o
= density for the phase o
(/)
s
= mass absorption coefficient of the specimen (
s
is the linear
absorption coefficient of the specimen while
s
is the density of the
specimen)
If the value of (/)
s
is known then the amount of the phase o in the specimen can be
calculated. Unfortunately (/)
s
is not a constant as its value is dependant on the amounts
of the entire constituent phases in the specimen. This problem can be solved by using
internal standard method, which is one of the most widely applied techniques for
quantitative XRD. Assuming the specimen contains phase o (phase which need to be
quantified) and phase | (standard phase with known amount), the (/)
s
problem can be
eliminated by simply dividing the intensity equation for both phases to yield:
|
o
|
o
X
X
k
hkl
I
hkl
I
=
|
.
|
\
|
|
.
|
\
|
(eq. 5)
k = calibration constant derived from the plot of I
(hkl)o
/ I
(hkl)|
against X
o
/ X
|
Internal standard method is usually applicable in the determination of the composition of
multi-phases specimen. This method can be extended to the quantification of physical
mixture consisted of different crystallite solids. In the latter part of the experiment, the
students need to determine the composition (in weight percent) of an alkali halide
mixture by using the internal standard calibration method.
5
Experiment Procedures
The major steps in the acquisition of X-ray powder diffraction patterns are:
1. Sample preparation and mounting
2. Selection of suitable instrument parameters
X-ray: kV, mA and
Divergence and receiving slits
3. Data collection
Scanning range, step size, count time
4. Pattern processing
Smoothing
Stripping of K
o2
Peak search
Peak correction
Store/print the diffractogram
5. Interpretation
(NOTE: X-ray radiations are VERY DANGEROUS and all students MUST OBEY the
safety regulations listed inside the X-ray instrument room. NEVER attempt to operate
the X-ray instrument unless you have been trained properly in handling the X-ray
instrument.)
Part A. Analysis of NaCl and KCl
Sample preparation
1. Prepare samples of NaCl : KCl mixtures with various composition as according to
Table 2. (NOTE: Sample A1 and A5 are pure alkali halide)
2. Mix the mixture in the beaker thoroughly by using a metal spatula.
3. Grind the mixtures by using mortar and pestle.
4. Acquire six XRD sample holders and Unknown A from the lab technicians. The
sample holder has a circular well for mounting the sample.
5. Transfer and mount the samples onto the XRD sample holders by using press
and pull sample loading method (NOTE: The sample is loaded into the circular
well and pressed down with a glass slide. After that the glass slide is carefully
pulled to the side. This method produces a mounted sample with an extremely flat
and smooth surface).
6. Label the sample holder properly.
Acquisition of X-ray powder diffraction patterns
1. Submit the samples to the lab technicians for powder XRD patterns acquisition
(NOTE: Please do not attempt to operate the powder XRD instrument).
2. Take note of the important components of the powder XRD instrument.
3. For pure KCl (Sample A1) and NaCl (Sample A5), use the following parameters:
2u range : 20 to 80
6
Step size : 0.05
For the rest of the sample (Sample A2, A3, and A4) and Unknown A, use the
following parameters:
2u range : 20 to 35
Step size : 0.05
4. After the acquisition of X-ray diffraction patterns, process the patterns by using
EVA software. Identify the 2u value and peak intensities for all the peaks.
5. Print out a copy of the XRD diffractograms. Students may duplicate the
diffractograms by using the photocopy machine.
Part B. Analysis of KCl and KBr
Sample preparation
1. Prepare samples of KCl : KBr mixtures with various composition as according to
Table 2. (NOTE: Sample B1 and B5 are pure alkali halide)
2. Mix the mixture in the beaker thoroughly by using a metal spatula.
3. Grind the mixtures by using mortar and pestle.
4. Acquire six XRD sample holders and Unknown B from the lab technicians. The
sample holder has a circular well for mounting the sample.
5. Transfer and mount the samples onto the XRD sample holders by using press
and pull sample loading method (NOTE: The sample is loaded into the circular
well and pressed down with a glass slide. After that the glass slide is carefully
pulled to the side. This method produces a mounted sample with an extremely flat
and smooth surface).
6. Label the sample holder properly.
Acquisition of X-ray powder diffraction patterns
1. Submit the samples to the lab technicians for powder XRD patterns acquisition
(NOTE: Please do not attempt to operate the powder XRD instrument).
2. Take note of the important components of the powder XRD instrument.
3. For pure KBr (Sample B1) and KCl (Sample B5), use the following parameters:
2u range : 20 to 80
Step size : 0.05
For the rest of the sample (Sample B2, B3, and B4) and Unknown B, use the
following parameters:
2u range : 20 to 35
Step size : 0.05
4. After the acquisition of X-ray diffraction patterns, process the patterns by using
EVA software. Identify the 2u value and peak intensities for all the peaks.
7
5. Print out a copy of the XRD diffractograms. Students may duplicate the
diffractograms by using the photocopy machine.
Table 2. Composition of alkali halides mixture
Part A. Mixtures of NaCl and KCl
Sample
Weight (gram)
Weight
%
(200) Peak
intensity
(200) Peak
intensity %
NaCl KCl NaCl NaCl KCl NaCl KCl
A1 0.0 2.0
A2 0.5 1.5
A3 1.0 1.0
A4 1.5 0.5
A5 2.0 0.0
Unknown A
Part B. Mixtures of KCl and KBr
Sample
Weight (gram)
Weight
%
(200) Peak
intensity
(200) Peak
intensity %
KCl KBr KBr KCl KBr KCl KBr
B1 0.0 2.0
B2 0.5 1.5
B3 1.0 1.0
B4 1.5 0.5
B5 2.0 0.0
Unknown B
8
Data Analysis
Qualitative analysis
The structural parameters for a particular crystallite sample can be obtained by
interpreting the X-ray diffraction patterns and such data interpretation can be performed
conveniently by using the EVA software. However, in this experiment the students
should not rely on EVA software in doing the interpretation. Interpretation of X-ray
diffraction pattern usually starts from indexing of the significant peaks. Manual indexing
of peaks can be performed by following these steps:
1. Identify all the significant peaks from the diffractogram of a pure alkali halide.
2. By using a spreadsheet program such as Excel, enter the positions of each peaks
and label the columns as 2-theta.
3. Construct a second column that equals sin
2
u.
4. Label the third column as h
2
+k
2
+l
2
. Construct this column by dividing the
values of sin
2
u with sin
2
u value of the first peak. If the Bravais lattice of the
crystal is simple cubic, the result of this operation should give an integer series
starting with one (Table 1). If the Bravais lattice is face-centered cubic, then this
column need to be multiply by 3 before the integer series can be obtained.
5. Once the Bravais lattice for the alkali halide has been identified, create a fourth
column that contains the expected integer values for that Bravais lattice (for
example 1,2,3,4,5... for simple cubic). Label this column as Integer.
6. Create a plot of sin
2
u against the integer and obtain the best-fitted line for the plot.
The slope of the plot is equals (
2
/4a
2
). Calculate the unit cell dimension, a.
7. Calculate the crystallographic density of the alkali halide. Example: The face-
centered cubic cell contains four molecules. Therefore the crystallographic
density =mass of four molecules / volume of one unit cell.
8. Complete Table 3 and compare the crystallographic density value obtained with
the macroscopic density.
9. Sketch out the structure of the alkali halides. It is known that K
+
has an ionic radii
of 1.34 . Find out the ionic radii of the rest of the ions (Na
+
, Cl
-
and/or Br
-
) from
the crystal structure, assuming that the cation-anion contacts determine the edge
length of the ions.
Table 3. Structural parameters for alkali halides
Salt
Molecular
weight
(gmol
-1
)
Density
(gcm
-3
)
Bravais
lattice type
Unit cell
dimension
()
Crystallographic
density
(gcm
-3
)
NaCl 58.443 2.165
KCl 74.551 1.984
KBr 119.002 2.75
9
Qualitative analysis
1. Identify all the significant peaks on the diffractograms for sample 2, 3 and 4 and
Unknown A (or Unknown B) by making comparison with the diffractogram for
pure alkali halides.
2. Complete Table 2 by recording the intensity of the (200) peak on the
diffractograms for all the samples.
3. Calculate the peak intensity ratio and plot a calibration curve of peak intensity
ratio against weight percent of NaCl (or KBr).
4. Determine the composition of the unknown sample by using the calibration curve.
Questions
1. Explain why the (111) peak appears as a weak peak on the diffractograms of NaCl
or KBr, but disappears on the diffractogram of KCl.
2. Tungsten, also known as Wolfram, is a chemical element with very high melting
point. It has an atomic weight of 183.84 gmol
-1
and a macroscopic density of
19.25 gcm
-1
. The following diffraction data of Tungsten is obtained with Cu K
o1
radiation. Determine the Bravais lattice and unit cell dimension of Tungsten by
interpreting the diffraction data. It is known that the unit cell of Tungsten is a
cubic system.
2u (degree) Relative intensity (%)
40.262 100
58.251 15
73.184 23
86.996 8
100.632 11
114.923 4
References
[1] V. K. Pecharsky and P. Y. Zavalij, Fundamentals of Powder Diffraction and
Structural Characterization of Materials, Kluwer Academic Publishers, 2003
[2] A. Clearfield, J . Reibenspies and N. Bhuvanesh (eds.), Principles and Applications
of Powder Diffraction, Wiley, 2008
[3] R. J enkins and R. L. Snyder, Introduction to X-ray Powder Diffractometry, J ohn
Wiley & Sons, Inc, 1996
1
5. Activated Dienophiles in DielsAlder Cycloadditions
The most common (and synthetically most useful) DielsAlder reactions involve electron-
rich dienes and electron-deficient dienophiles.
Y
X
Y
X
Y= R, OR
X= CN, CHO, CO
2
H
The rate of these reactions generally increases with the donor ability of the diene
substituent, Y, and with the p acceptor ability of the dienophile substituent, X. This behavior
can be rationalized using Frontier Molecular Orbital (FMO) theory by examining the
interaction of the dienes highest-occupied molecular orbital (HOMO) and the dienophiles
lowest-unoccupied molecular orbital (LUMO).
Orbital
Energy
HOMO
LUMO
diene dienophile
The HOMOLUMO interaction lowers the reaction barrier by stabilizing the electrons in the
diene HOMO, and FMO theory suggests that this effect will be largest when the
HOMO
diene
LUMO
dienophile
energy difference is smallest. In other words, diene reactivity
should be positively correlated with HOMO energy, and dienophile reactivity should be
negatively correlated with LUMO energy.
Electrostatic interactions between the diene and dienophile may also play a significant role in
determining the reaction rate.
1
According to this view, rapid reactions occur when
1
S. D. Kahn, C. F. Pau, L. E. Overman and W. J. Hehre, J . Am. Chem. Soc., 108, 7381 (1986).
2
electrostatic interactions between the diene and dienophile are most attractive (least
repulsive). Thus, diene reactivity should increase as the electrostatic potential over the face
of the diene becomes more negative, and dienophile reactivity should increase as the
electrostatic potential over the face of the dienophile is made more positive.
The FMO and electrostatic models can also be used to predict the regiochemistry of a
cycloaddition reaction. According to the FMO model, the best HOMOLUMO interaction
for a given diene-dienophile pair results when there is good overlap between the interacting
orbitals. Thus, the best orientation for two unsymmetrical reactants is usually the one that
aligns the HOMO and LUMO so that the atomic orbitals that contribute most to each
molecular orbital are able to overlap.
2
The electrostatic potential model suggests that the best orientation is the one that brings
together the region of most negative potential on the diene with the region of most positive
potential on the dienophile.
In this experiment, you will explore to what extent the behaviour of a series of dienophiles
(cyanoalkenes) can be correlated with either their frontier molecular orbitals and/or their
electrostatic potentials as provided by ab initio calculations at HF/3-21G level.
Procedure
2
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976.
Experimental relative rates for DielsAlder cycloadditions of cyclopentadiene and
various dienophiles
3
1) Rates of DielsAlder cycloadditions:
Build the dienophiles listed in the table below, and optimize their geometries using the HF/3-
21G level of theory.
To build the structure:
1) Double click on the GaussView shortcut.
2) Click on File and choose New and choose Create MolGroup and a purple
screen to build the molecule will appear (Figure A).
3) From the Element fragment , choose a sp2 carbon and build 2 together to form
an ethene (Figure B).
4) Substitute a hydrogen with a cyano group from R-Group Fragments to form
the acrylonitrile (Figure C)
5) Minimize the molecule using the Clean icon .
6) Undo any errors with Ctrl + Z. Save the molecule on desktop as .gjf file.
3
J. Sauer, H. Wiest and A. Mielert, Chem. Ber., 97, 3164 (1964).
dienophile
3
relative rate (k
rel
)
acrylnitrile 1
trans-1,2-dicyanoethylene 78
cis-1,2-dicyanoethylene 88
1,1-dicyanoethylene 4.4 10
4
tricyanoethylene 4.6 10
5
tetracyanoethylene 4.1 10
7
4
7) When acrylonitrile has been optimized, add cyano groups to the optimized structure to
build the other dienophiles. (Optimized structure can be found by opening the log file
in Guassview in the same location as the gjf file)
Mouse Control
Left click: Press and hold on to left click and drag to rotate
Centre click/wheel: Press and hold to translate/move the molecule
Right click: Press and hold; dragging up and down Zooms in and out of the molecule.
Dragging left and right rotates the molecule in the plane of the screen.
Figure A
5
Figure B
Figure C
6
To optimize a structure:
1) Go the Calculate drop down menu and choose the Gaussian option.
2) Under the J ob Type drop-down menu choose Optimization (Figure D).
3) Under method, choose Hartree-Fock and use the 3-21G basis set. (Figure E).
4) Under Link 0, set the RAM as 1000Mb.
** Remember to have a different .chk file name for each dienophile as you will need
the LUMO map for the later exercises.
5) Input the additional keywords pop=npa to calculate the charge.
6) Repeat steps 1 to 5 for all the 6 dienophiles
Figure D.
7
Figure E.
Record the HF/3-21G LUMO energy (in eV) of each dienophile, and plot these energies
against the log of the experimental k
rel
values.
You can assess the LUMO for HOMOLUMO band gap by looking at the log file for the
first virtual eigenvalue (Al pha vi r t . ei genval ues) .
Using MS word to open the log file, using the Find function (Ctrl + F), change the options
from More to up instead of down and search Alpha from the last page to search for
the last optimization eigenvalues (Figure F). Convert the values from hartrees to eV.
From log file in MS Word:
Al pha occ. ei genval ues - - - 15. 65673 - 15. 65503 - 15. 65385 - 11. 40083 - 11. 38117
Al pha occ. ei genval ues - - - 11. 34508 - 11. 34262 - 11. 34195 - 1. 31718 - 1. 30679
Al pha occ. ei genval ues - - - 1. 30193 - 1. 20515 - 1. 01572 - 0. 87084 - 0. 80044
Al pha occ. ei genval ues - - - 0. 71553 - 0. 62530 - 0. 60821 - 0. 60578 - 0. 59781
Al pha occ. ei genval ues - - - 0. 55117 - 0. 53845 - 0. 53102 - 0. 52840 - 0. 51820
Al pha occ. ei genval ues - - - 0. 42897 HOMO
Al pha vi r t . ei genval ues - - - 0. 01183 LUMO 0. 14692 0. 17737 0. 19951
Al pha vi r t . ei genval ues - - 0. 22303 0. 23290 0. 28462 0. 30118 0. 33623
Al pha vi r t . ei genval ues - - 0. 40943 0. 45500 0. 53610 0. 56665 0. 59386
Figure F
8
The FMO model actually depends on two factors: the HOMO LUMO energy difference
and the degree of the HOMOLUMO overlap. Is there a relationship between the value of
the LUMO and the dienophile reactivity? If there is, is this relationship consistent with the
FMO model?
Next, consider the electrostatic argument.
1) Open the log file (Figure G) in Gaussview by clicking on File and picking the
Open option in the drop down menu. Choose File of Type as Gaussian Output
Files and look for the log file in the same folder as the input file (.gjf file).
2) Go to Results and under the drop down window, choose Charges and Show
charge number (Figure H).
3) Record the most positive charge found on the sp
2
bond forming carbon. Plot this
quantity against log(k
rel
).
What does the charge describe about the electronic properties of each atom? Are the two
correlated? If so, is the direction of the correlation consistent with the electrostatic
character of the dienophiles?
Figure G
9
Figure H
2) Regioselectivity in Diels-Alder cycloadditions:
You will use the reaction of 1-methylcyclopentadiene (MCP) with various unsymmetrical
dienophiles (acrylonitrile, 1,1-dicyanoethylene, and tricyanoethylene) to examine FMO
and electrostatic potential-based analyses of regioselectivity.
** (Regioselectivity is not equivalent to endo/exo selectivity)
10
Build 1-methylcyclopentadiene, optimize its HF/3-21G geometry.
1) In the Ring Fragments , choose cyclopentadiene and build. (Figure I)
2) Add a sp3 carbon to the H you want to substitute as the methyl using the Element
Fragment
3) Repeat optimization step 1 to 5 from Exercise 1 to optimize the structure.
Figure I
Display the HOMO of the diene and LUMO of the dienophiles using the checkpoint file.
1) Under File, choose Open in the drop down menu and set File of Type as
Gaussian Checkpoint Files. The .chk files are located in the directory
C:\G03W\Scratch.
2) Go to the Results menus again and choose Surfaces.
3) Under the Cube Actions drop-down menus choose New Cube. Yet another
dialog appears called the Generate Cubes dialog.
4) Under the Orbitals: drop-down menu, choose the HOMO or LUMO
accordingly. (Figure J)
5) Go to the Cubes Available: drop down menu and choose the HOMO or
LUMO accordingly.
6) Go to the Surface Actions and in the drop down menu and choose New Surface.
11
Figure J
Which end of the diene is best suited for overlap with an unsymmetrical dienophile? Next,
examine LUMO maps of the three unsymmetrical dienophiles. Which alkene carbon is best
suited for overlap? What product regioisomers are predicted by the overlap? Do you arrive
at the same predictions using resonance arguments? (Your answer should include drawings
of the specific resonance structures that your predictions are based on.)
Next examine the NBO charges of the diene and the three dienophiles. Which sp2 carbon
involved in the bond formation of the diene has the most negative potential? Which end of
each dienophile has the most positive potential? What product regioisomers are predicted by
the electrostatic model? Are the Molecular Orbitals and electrostatic predictions the same?
3) Lewis Acidity effects on Rate
Lewis acids such as BF
3
generally increase both the rate and regioselectivity of DielsAlder
reactions. These effects might be due to enhanced and more selective frontier orbital
interactions, or they might be due to changes in the nature of key electrostatic interactions.
Examine the effect of a simple Lewis acid, H
+
, on the reaction of acrylonitrile and 1-
methylcyclopentadiene. Lewis acids preferentially bind to the strongest Lewis base present,
the nitrogen lone pair of acrylonitrile.
12
Therefore, build an N-protonated acrylonitrile cation, optimize its geometry using the HF/3-
21G level of theory, and use the results to evaluate the reactivity and regioselectivity of this
dienophile.
1) Use the Add Valence icon to add a hydrogen atom to the N of acrylonitrile.
2) Repeat optimization step 1 to 5 from Exercise 1 but CHANGE THE CHARGE TO 1.
Which factors appear to contribute to this dienophile's enhanced reactivity and selectivity?
4) Transition state and kinetics
The most direct way to evaluate DielsAlder selectivity is to calculate energy barriers for
reactions involving the dienophiles. Build 4 transition states for the 4 possible products of
the reaction between 1-methylcyclopentadiene and acrylonitrile, using the template
method. That is, add cyano groups to a simpler transition state template of cyclopentadiene
and ethene:
Create the geometry of the transition state for constrained optimization
a. Open the optimized 1-methylcyclopentadiene.log and build an ethene inside the same
screen as the MCP (Figure K)
b. Orientate the ethene towards the two bond forming carbons in the optimized MCP (Figure
L). Press and hold on Alt, use the centre click to shift the molecules individually to the
desired position of the pseudo C-C bond formation in the Diels Alder reaction.
c. Add single bonds to the bond forming carbons using the Modify Bond option
and minimize the molecule using the Clean function (Figure M).
d. Set both the bond lengths to 2.19 (Figure M) using the Modify Bond option .
13
Figure K
Figure L
Figure M
14
e) Add the constraints to the two forming C-C bonds.
I. Click on the Redundant Coordinate Editor icon ( Figure N)
II. Click on the Add new constraints icon (Figure O).
III. Set the parameter (Bond) that you want to constrain under Coordinates and choose
Freeze coordinate (Figure O). Choose the two atoms which constitute the bond you
want to constrain.
IV. Go to Set value and set it as 2.19 A.
V. Repeat step II to IV for the other bond.
f) Optimize the constrained geometry by repeating optimization step 1 to 4 from Ex 1,
EXCLUDING the step of inputting the additional keyword.
Constrained optimization
Figure N
Click on R icon to
input constraints
15
Figure O
Use the optimized constraint structure to search for the HF/3-21G transition state.
1. Under Job type choose Opt+Freq. (Figure P)
2. Under Optimize choose TS(Berny),
3. Under Calculate Force Constants, choose Once and under Compute Raman,
choose No
4. Under method, input the usual Hartree-Fock /3-21g, 0 charge, singlet. (Figure Q)
5. Insert keyword opt=noeigentest and run the calculation
Add the cyano substituent at different position of the ethene in the obtained transition state to
generate the inputs for the different stereoisomers. Repeat the above steps 1-5. . (DO NOT
RUN CONSTRAI NED OPTI MI ZATI ON STEPS a to f AGAI N )
Operation specified Parameters
chosen
Parameters to be altered
Value to be constrained Add new
constraint
16
Figure P
Figure Q
17
Verify that these are transition states by their vibrational frequencies (a transition state
has only one imaginary frequency).
Use the HF/3-21G energy of each transition state along with those of the reactants to
obtain the energy barriers for each cycloaddition. Compare the activation barriers and
use Boltzmann distribution to identify the composition of the products (assuming the
degeneracy is the same for all the stereoisomers at standard state, 298K/1 atm).
Is the composition correlated with the regioselectivity predicted? What are the reasons
for the different in stabilities of the transition states?
E
A
= E
TS
E
Reactants
= E
TS
E
MCP
E
dienophile
To extract the energy of the operation, open the .log file in MS words and go to the
end of the file and find the line \HF=. The energy is in expressed in hartrees.
Sometimes even though the TS search did not terminate properly, both the vibration
calculation and TS search are completed. Open the log file in Guassview and click on
Results and choose Vibration. If the vibration frequencies are present means the
job is completed. To extract the energy from the improperly terminated files, open the
log file in MS words, go to the bottom of the file and search # upwards. It will bring
you to the start of the frequency calculation. Above it is the termination of the TS
search and you can look for the /HF there.