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13.

14
13
C NMR Spectroscopy

13
HHand
and 13CCNMR
NMRcompared:
compared:

1
1

both give us information about the


number of chemically nonequivalent
nuclei (nonequivalent hydrogens or
nonequivalent carbons)
both give us information about the
environment of the nuclei (hybridization
state, attached atoms, etc.)

13
HHand
and 13CCNMR
NMRcompared:
compared:

1
1

the signal for the NMR of a 13 C nucleus is


10-4 times weaker than the signal for a
hydrogen nucleus
a signal for a 13C nucleus is only about 1% as
intense as that for 1H because of the magnetic
properties of the nuclei, and
at the "natural abundance" level only 1.1% of
all the C atoms in a sample are 13C (most are
12C)

13
HHand
and 13CCNMR
NMRcompared:
compared:

1
1

C signals are spread over a much wider


range than 1H signals making it easier to
identify and count individual nuclei
13

Check the spectra on the next slides: Figure


13.20 (a) shows the 1H NMR spectrum of 1chloropentane; Figure 13.20 (b) shows the
13C spectrum. It is much easier to identify the
compound as 1-chloropentane by its 13C
spectrum than by its 1H spectrum.

Figure 13.20(a) (page 511)

9.0

8.0

7.0

6.0

CH3

ClCH2

ClCH2CH2CH2CH2CH3

10.0

5.0

4.0

3.0

Chemical shift (, ppm)

2.0

1.0

Figure 13.20(b) (page 511)


Note: in these spectra the peak intensities are
not exactly proportional to the number of
carbon atoms.

13

ClCH2CH2CH2CH2CH3
a separate, distinct
peak appears for
each of the 5
carbons
200

180

160

140

120

CDCl3

100

80

60

Chemical shift (, ppm)

40

20

13.15
13
C Chemical Shifts
are measured in ppm ()
from the carbons of TMS

CCChemical
Chemicalshifts
shiftsare
aremost
mostaffected
affectedby:
by:

13
13

hybridization state of carbon


electronegativity of groups attached to carbon

Examples
Examples(chemical
(chemicalshifts
shiftsininppm
ppmfrom
fromTMS)
TMS)

23

138
sp3 hybridized carbon is more shielded than sp2

Examples
Examples(chemical
(chemicalshifts
shiftsininppm
ppmfrom
fromTMS)
TMS)

OH
61

O
202

sp3 hybridized carbon is more shielded than sp2

Examples
Examples(chemical
(chemicalshifts
shiftsininppm
ppmfrom
fromTMS)
TMS)

23

OH
61

an electronegative atom deshields the carbon


to which it is attached

Examples
Examples(chemical
(chemicalshifts
shiftsininppm
ppmfrom
fromTMS)
TMS)

138

O
202

an electronegative atom deshields the carbon


to which it is attached

Table
Table13.3
13.3(p
(p513)
513)
Type of carbon Chemical shift (),
ppm

RCH3

0-35

R2CH2

15-40

R3CH

25-50

R4C

30-40

Table
Table13.3
13.3(p
(p513)
513)
Type of carbon Chemical shift (), Type of carbon
ppm

Chemical shift (),


ppm

RCH3

0-35

RC

CR

65-90

R2CH2

15-40

R2C

CR2

100-150

R3CH
R4C

25-50
30-40

110-175

Table
Table13.3
13.3(p
(p513)
513)
Type of carbon Chemical shift (),
ppm

RCH2Br

20-40

RCH2Cl

25-50

RCH2NH2

35-50

RCH2OH

50-65

RCH2OR

50-65

Table
Table13.3
13.3(p
(p513)
513)
Type of carbon Chemical shift (), Type of carbon
ppm

Chemical shift (),


ppm

RCH2Br

20-40

RCH2Cl

25-50

RCH2NH2

35-50

RCH2OH

50-65

RCR

RCH2OR

50-65

RCOR

160-185

190-220