N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
80
4 13 C NMR
80
4 13 C NMR
13 C Chemical Shifts of 1-Substituted n-Octanes (δ in ppm)
Substituent
1
2
3
4
5
6
7
8
–CH 2 –CH 2 –CH 2 –CH 2 –CH 2 –CH 2 –CH 2 –CH 3
–H
14.1 22.8 32.1 29.5 29.5 32.1 22.8 14.1
–CH=CH 2
34.5 ~29.6 ~29.6 ~29.6 ~29.6 32.2 23.0 13.9
–phenyl
36.2 31.7 ~29.6 ~29.6 ~29.6 32.1 22.8 14.1
–F
84.2 30.6 25.3 29.3 29.3 31.9 22.7 14.1
–Cl
45.1 32.8 27.0 29.0 29.2 31.9 22.8 14.1
–Br
33.8 33.0 28.3 28.8 29.2 31.8 22.7 14.1
–I
6.9 33.7 30.6 28.6 29.1 31.8 22.6 14.1
–OH
63.1 32.9 25.9 29.5 29.4 31.9 22.8 14.1
–O–n-C 8 H 17
71.1 30.0 26.3 29.6 29.4 32.0 22.8 14.1
–O–phenyl
68.0 26.2 29.3 29.4 29.4 31.9 22.7 14.1
–OCO–n-propyl 64.4 28.8 26.1 29.3 29.3 31.9 22.8 14.1
–OCO–phenyl
65.1 28.8 26.1 29.3 29.3 31.9 22.7 14.1
–ONO
68.3 29.2 26.0 29.3 29.3 31.9 22.7 14.0
–NH 2
42.4 34.1 27.0 29.6 29.4 31.9 22.7 14.1
–N(CH 3 ) 2
60.1 29.5* ≈27.9* ≈27.7* 29.7* 32.0 22.8 14.4
–N + (CH 3 ) 3 Cl – 66.6 26.2 23.2 29.1* 29.0* 31.6 22.5 14.0
–NO 2
75.8 26.2 27.9 ≈29.6 ≈29.6 31.4 22.6 14.0
–C– – – N
17.2 25.5 ≈29.9 ≈29.9 ≈29.9 31.8 22.7 14.0
–SH
24.7 34.2 28.5 29.2 29.1 31.9 22.7 14.1
–SCH 3
34.5 29.0 29.4 29.4 29.4 31.9 22.8 14.1
–S(O)–n-C 8 H 17 52.6 ≈29.1 ≈29.1 ≈29.1 ≈29.1 31.8 22.7 14.1
–CHO
44.0 22.2 ≈29.3 ≈29.3 ≈29.3 31.9 22.7 14.1
–COCH 3
43.7 24.1 ≈29.5 ≈29.5 ≈29.5 32.0 22.8 14.1
–CO–phenyl
38.6 24.4 29.5 29.5 29.5 31.9 22.7 14.0
–COOH
34.2 24.8 ≈29.3 ≈29.3 ≈29.3 31.9 22.7 14.1
–COOCH 3
34.2 25.1 29.3 29.3 29.3 31.9 22.8 14.1
–CONH 2
35.5 25.4 29.1 29.1 29.1 31.6 22.3 14.0
–COCl
47.2 25.1 28.5 29.1 29.1 31.8 22.7 14.1
–Si(OCH 3 ) 3
9.2 22.7 33.2 29.3 29.3 32.0 22.7 14.1
* Assignment uncertain
C
X
O
N
S
O
||
C
Si