N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
100
4 13 C NMR
Effect of Substituents on 13 C Chemical Shifts of Monosubstituted Benzenes
(δ in ppm)
R
1
2
3
4
δ C i
= 128.5 + Z i
Substituent R
Z 1
Z 2
Z 3
Z 4
–CH 3
9.2
0.7
-0.1
-3.0
–CH 2 CH 3
11.7
-0.6
-0.1
-2.8
–CH 2 CH 2 CH 3
10.3
-0.2
0.1
-2.7
–CH(CH 3 ) 2
20.2
-2.2
-0.3
-2.8
–CH 2 CH 2 CH 2 CH 3
10.9
-0.2
-0.2
-2.8
–C(CH 3 ) 3
18.6
-3.3
-0.4
-3.1
–cyclopropyl
15.1
-3.3
-0.6
-3.6
–cyclopentyl
17.8
-1.5
-0.4
-2.9
–cyclohexyl
16.3
-1.8
-0.3
-2.8
–1-adamantyl
22.2
-2.9
-0.5
-3.1
–CH 2 F
8.5
-0.7
0.4
0.5
–CF 3
2.5
-3.2
0.3
3.3
–CH 2 Cl
9.3
0.3
0.2
0.0
–CHCl 2
11.9
-2.4
0.1
1.2
–CCl 3
16.3
-1.7
-0.1
1.8
–CH 2 Br
9.5
0.7
0.3
0.2
–CH 2 I
10.5
0.0
0.0
-0.9
–CH 2 OH
12.4
-1.2
0.2
-1.1
–CH 2 OCH 3
8.7
-0.9
-0.1
-0.9
–CH 2 NH 2
14.9
-1.4
-0.2
-2.0
–CH 2 NHCH 3
12.6
-0.3
-0.3
-1.8
–CH 2 N(CH 3 ) 2
7.8
0.5
-0.3
-1.5
–CH 2 NO 2
2.2
2.2
2.2
1.2
–CH 2 CN
1.6
0.5
-0.8
-0.7
–CH 2 SH
12.5
-0.6
0.0
-1.6
–CH 2 SCH 3
9.8
0.4
-0.1
-1.6
–CH 2 S(O)CH 3
0.8
1.5
0.4
-0.2
–CH 2 S(O) 2 CH 3
-0.1
2.1
0.6
0.6
–CH 2 CHO
7.4
1.3
0.5
-1.1
–CH 2 COCH 3
5.8
0.8
0.1
-1.6
–CH 2 COOH
6.5
1.4
0.4
-1.2
–CH 2 Li
32.2
-22.0
-0.4
-24.3
–CH=CH 2
8.9
-2.3
-0.1
-0.8
–C(CH 3 )=CH 2
12.6
-3.1
-0.4
-1.2
–C – – – CH
-6.2
3.6
-0.4
-0.3
–phenyl
8.1
-1.1
0.5
-1.1
–2-pyridyl
11.2
-1.4
0.5
-1.4
–4-pyridyl
9.6
-1.6
0.5
0.5
C