N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
104
4 13 C NMR
Effect of Substituents in Position 1 on 13 C Chemical Shifts of Monosubstituted
Naphthalenes (δ in ppm)
R
for R: H
δ C 1
= 128.0
δ C 2
= 125.9
δ C 9
= 133.6
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
6.0 0.5 0.6 -1.8 0.3 -0.7 -0.5 -4.1 -1.1 -0.2
–C(CH 3 ) 3
17.9 -2.8 -0.9 -0.6 1.6 -1.4 -1.4 -1.2 -1.6 2.2
–CH 2 Br
4.0 1.1 -0.9 1.3 0.5 -0.1 0.3 -4.6 -2.8 0.1
–CH 2 OH
8.2 -0.9 -0.6 0.1 0.5 -0.3 0.1 -4.5 -2.6 0.0
–CF 3
-1.9 -1.3 -1.8 5.0 1.0 0.8 2.0 -3.4 1.0 -3.9
–F
31.5 -16.1 0.1 -3.8 0.1 1.4 0.7 -7.1 -9.3 2.1
–Cl
3.9 0.2 -0.2 -0.9 0.2 3.1 0.8 -3.6 -2.8 1.0
–Br
-5.4 3.6 -0.2 -0.5 -0.1 0.4 1.0 -1.3 -2.0 0.6
–I
-28.4 12.3 1.7 1.7 1.4 1.6 2.6 4.4 1.3 1.3
–OH
23.5 -17.2 -0.1 -7.3 -0.4 0.5 0.3 -6.6 -9.3 1.0
–OCH 3
27.3 -22.3 -0.2 -7.9 -0.7 0.3 -0.9 -6.1 -8.1 0.8
–OCOCH 3
18.6 -7.9 -0.6 -2.1 0.0 0.4 0.4 -6.9 -6.9 0.9
–NH 2
14.0 -16.5 0.3 -9.3 0.3 -0.3 -1.3 -7.3 -10.2 0.6
–N(CH 3 ) 2
23.7 -11.2 0.6 -4.6 1.0 0.4 -0.3 -3.2 -3.9 2.1
–NH 3
+
-3.8 -4.6 -0.9 3.4 1.4 2.1 2.8 -9.0 -7.4 1.2
–NHCOCH 3
5.7 -4.4 -0.5 -3.0 0.0 -0.1 -0.3 -5.3 -5.9 0.1
–NO 2
18.5 -2.1 -2.0 6.5 0.5 1.3 3.4 -5.1 -8.7 0.6
–C – – – N
-19.2 5.1 -2.4 3.8 -0.7 0.2 1.2 -4.5 -2.8 -2.2
–CHO
2.9 10.8 -1.4 6.7 0.2 0.6 2.7 -3.5 -3.6 -0.3
–COCH 3
6.9 2.9 -1.7 4.9 0.3 0.4 2.0 -2.0 -3.5 0.2
–COOH
-1.5 3.6 -2.4 4.3 -0.6 -0.9 0.6 -3.2 -3.2 -0.8
–COOCH 3
-0.9 4.5 -1.2 5.4 0.7 0.5 1.9 -1.8 -1.9 0.5
–CON(CH 3 ) 2
6.8 -2.1 -0.8 0.9 0.4 0.4 1.0 0.1 -4.1 -0.2
–COCl
1.2 10.6 -0.5 9.3 1.9 2.1 4.5 -2.1 -2.1 1.0
–Si(CH 3 ) 3
9.8 5.1 -0.4 1.7 1.2 -0.8 -0.7 0.1 3.8 0.2
C
X
O
N
O
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C