N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.5 Aromatic Hydrocarbons
105
Effect of Substituents in Position 2 on 13 C Chemical Shifts of Monosubstituted
Naphthalenes (δ in ppm)
for R: H
δ C 1
= 128.0
δ C 2
= 125.9
δ C 9
= 133.6
R
1
2
7
3
6
4
5
10
9
8
Substituent R C-1 C-2 C-3 C-4 C-5 C-6 C-7 C-8 C-9 C-10
–CH 3
-1.3 9.3 2.0 -0.8 -0.5 -1.1 -0.2 -0.6 -0.1 -2.0
–C(CH 3 ) 3
-3.3 22.5 -3.0 -0.4 0.0 -0.7 -0.2 -0.6 0.4 -1.3
–CH 2 Br
-1.7 9.0 1.9 -0.4 -0.5 0.7 0.3 0.6 -0.6 -0.7
–CH 2 OH
-2.7 12.3 -4.4 -0.1 -0.4* -0.2* 0.1* -0.2* -0.3 -0.8
–CF 3
-2.0 1.9 -4.2 1.1* 0.1* 2.4* 1.5 1.1 -1.1 1.3
–F
-17.0 34.9 -9.6 2.4 0.0 -0.7 1.1 -0.6 0.7 -3.0
–Cl
-1.4 5.7 0.8 1.5 -0.2 0.2 1.1 -1.1 0.7 -1.9
–Br
1.8 -6.2 3.1 1.5 -0.3 0.2 0.8 -1.1 -2.0 0.7
–I
9.2 -34.1 9.0 2.3 0.5 1.3 1.5 -0.6 2.1 -0.8
–OH
-18.6 27.3 -8.3 1.8 -0.3 -2.4 0.5 -1.7 0.9 -4.7
–OCH 3
-22.2 31.8 -7.1 1.5 -0.3 -2.2 0.5 -1.2 1.0 -4.3
–OCOCH 3
-9.5 22.5 -4.8 1.3 -0.4 -0.3 0.6 -0.4 0.1 -2.2
–NH 2
-20.6 16.7 -8.9 -0.2 -1.6 -4.8 -0.9 -3.5 -0.1 -7.0
–N(CH 3 ) 2
-21.1 23.6 -8.8 1.2 0.0 -3.4 0.7 -1.1 2.4 -5.9
–NH 3
+
-5.9 -0.3 -6.5 3.2 0.2 2.3 2.0 0.2 0.1 -0.3
–NHCOCH 3 -11.0 9.6 -5.7 0.6 -0.4* -0.9 1.6* -1.6 0.2 -3.0
–NO 2
-3.4 20.0 -6.7 1.7 0.1 4.0 2.2 2.1 -1.1 2.4
–C– – – N
5.8 -16.7 0.1 1.0 -0.2 3.0 1.6 0.2 -1.6 0.7
–CHO
6.2 7.9 -3.6 0.8 -0.3 2.9 0.9 1.8 2.4 -1.4
–COCH 3
1.9 8.3 -2.2 0.2 -0.4 2.3 0.7 1.4 1.8 -1.3
–COOH
2.7 2.4 -0.6 0.2 -0.3 2.4 0.9 1.3 -1.3 1.5
–COOCH 3
3.0 1.8 -0.5 0.2 -0.1 2.4 0.9 1.4 -1.0 1.9
–COCl
2.5 9.1 -0.7 0.2* -0.4 2.2* 0.8 1.2
-1.4
–Si(CH 3 ) 3
5.8 11.9 3.9 -1.0 0.1 0.3 -0.2 0.1 -0.5 0.2
* Assignment uncertain
C
X
O
N
O
||
C