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13C NMR

The document provides an overview of 13C NMR spectroscopy, detailing chemical shifts, spin-spin coupling, and the identification of various carbon functionalities. It includes correlation charts for chemical shifts of different carbon types and examples of spectra analysis. Additionally, it presents a problem-solving section for determining the structural formula of an unknown compound using NMR and IR data.

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17 views15 pages

13C NMR

The document provides an overview of 13C NMR spectroscopy, detailing chemical shifts, spin-spin coupling, and the identification of various carbon functionalities. It includes correlation charts for chemical shifts of different carbon types and examples of spectra analysis. Additionally, it presents a problem-solving section for determining the structural formula of an unknown compound using NMR and IR data.

Uploaded by

gayovi8834
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd

1

2
 13
C Nucleis are shielding
• Electronegativity
• Hybridization

 C spectra are typically recorded from 0 –


13

220 ppm; with the zero being the methyl


carbon in TMS

 Several functionalities appear directly on 13


C
NMR which are often easy to identify –
• Quaternary carbons
• ipso carbons
• Carbonyl carbons 3
General Correlation Chart – 13
C NMR

Here are the general regions for 13


C chemical shifts:

sp3 carbon

C-EWG
13

alkyne carbons CH3

Si
alkene carbons
H3 C CH
CH3 3
aromatic carbons

carbonyl carbons

220 200 180 160 140 120 100 80 60 40 20 0.0

downfield  (ppm) upfield


deshielded shielded
higher E lower E
4
General Correlation Chart – 13
C NMR

Specifically for 13
C chemical shifts of carbonyls
(13C=O)
anhydrides

acid chlorides

aldehydes amides

conj. ketones esters

ketones carboxylic acids nitriles

220 210 200 190 180 170 160 150 140 130 120 110

5
6
Spin-Spin Coupling – 13
C NMR

The splitting follows the simple n+1 rule

H H
13 13 13 13
C C C H
C
H H H

quaternary methine methylene quaternary

singlet doublet triplet quartet

7
A comparison of proton decoupled (top) and off-
resonance proton decoupled (bottom) 13C-NMR spectra
of diethyl phthalate. 4 O or 1 5 6

=
3 2 COCH2CH3

COCH2CH3

=
O
diethyl phthalate

C-3 (1 H)
and
C-4 (1 H) From the splittings in the off-
C-5 (2 H) resonance proton decoupled
spectrum, the number of H
C-6 (3 H) attached to each carbon (n+1
C-2 (0 H) rule) may be determined. If the
resonance is a singlet, there are
C-1 (0 H) no H attached.
Spin-Spin Coupling – C NMR
13

A comparison of two 13
C NMR Spectra
H Coupled (undecoupled)
1

H Decoupled
1

9
C  pulse
13

13
C FID

10
Problems
&
Solves

11
found. One septet 2.72 (J = 6.7 Hz) and another is doublet at 1.33 (J = 6.7 Hz).

12
Problem/Solve

H NMR
1

IR
6H

4H
4H

C NMR
13

13
Prtoblem
A unknown sample gave (UV) a characteristic
band at 275 m, max 17. In IR, bands are formed
at 2941-2857 (m) 1715 (s), and 1460 cm-1 (m). In
NMR, three signals appear at (i) (ppm) = 2.48
(quartet, 2H), 2.12 (singlet, 3H), and 1.07
(triplet, 3H) and molecular mass m/z = 72.
Determine the structural formula of the
compound.

14
Solution

15

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