13.

14
13C NMR Spectroscopy
 1H and 13C NMR compared:

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.)
 1H and 13C NMR compared:

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)
 1H and 13C NMR compared:

13C signals are spread over a much wider

range than 1H signals making it easier to
identify and count individual nuclei
Check the spectra on the next slides: Figure
13.20 (a) shows the 1H NMR spectrum of 1-
chloropentane; 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.
Typical ppm (d) Ranges in
C-13 NMR
 NS=1600

NS=16000
 13C

ClCH2CH2CH2CH2CH3
a separate, distinct
peak appears for
each of the 5
carbons CDCl3

200 180 160 140 120 100 80 60 40 20 0

Chemical shift (d, ppm)

 13C Chemical shifts are most affected by:

• hybridization state of carbon

• electronegativity of groups attached to carbon
 Examples (chemical shifts in ppm from TMS)

23

138

sp3 hybridized carbon is more shielded than sp2

 Examples (chemical shifts in ppm from TMS)

OH
61

202

sp3 hybridized carbon is more shielded than sp2

Examples (chemical shifts in ppm from TMS)

OH
23 61

an electronegative atom deshields the carbon

to which it is attached
Examples (chemical shifts in ppm from TMS)

138 202

an electronegative atom deshields the carbon

to which it is attached
 Chemical shifts for different type of carbon

Type of carbon Chemical shift (d),

ppm

RCH3 0-35

R2CH2 15-40

R3CH 25-50

R4C 30-40
 Chemical shifts for different type of carbon

Type of carbon Chemical shift (d), Type of carbon Chemical shift (d),
ppm ppm

RCH3 0-35 RC CR 65-90

R2CH2 15-40 R2C CR2 100-150

R3CH 25-50
110-175
R4C 30-40
 Carbon attached to electronegative atoms

Type of carbon Chemical shift (d),

ppm

RCH2Br 20-40

RCH2Cl 25-50

RCH2NH2 35-50

RCH2OH 50-65

RCH2OR 50-65
 Carbon with carbonyl attachment

Type of carbon Chemical shift (d), Type of carbon Chemical shift (d),
ppm ppm

RCH2Br 20-40 O

RCH2Cl 25-50 RCOR 160-185

RCH2NH2 35-50 O

RCH2OH 50-65 RCR 190-220

RCH2OR 50-65