N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.4 Alicyclics
95
13 C Chemical Shifts of Equatorially and Axially Monosubstituted Cyclohexanes
(δ in ppm)
Substituent R
a
b
c
d
a
b
c
d
–H
27.1 27.1 27.1 27.1
27.1 27.1 27.1 27.1
–CH 3
33.2 36.0 27.1 27.0
28.4 32.4 20.6 26.9
–CH 2 CH 3
40.1 33.4 26.9 27.2
35.5 30.0 21.4 27.1
–CH 2 CH 2 CH 3
40.0 33.6 26.6 26.9
–CH(CH 3 ) 2
44.6 30.0 26.8 27.3
41.1 30.2 21.6 27.1
–CH 2 CH 2 CH 2 CH 3
38.4 34.1 27.1 27.3
–C(CH 3 ) 3
48.8 28.1 27.7 27.1
–cyclohexyl
44.3 30.8 27.4 27.4
–CH=CH 2
42.1 32.3 26.0 27.1
37.0 30.0 21.2 27.1
–C– – – CH
28.7 32.1 25.2 24.4
28.0 30.0 21.2 25.7
–phenyl
45.1 34.9 27.4 26.7
35.2 30.1 21.9 27.7
–F
91.0 32.8 23.6 25.3
88.1 30.1 19.8 25.0
–Cl
59.8 37.4 26.1 25.4
60.1 33.9 20.4 26.0
–Br
52.4 38.3 27.3 25.6
55.4 34.9 21.5 26.4
–I
31.2 40.1 28.3 25.4
38.3 36.0 22.8 26.1
–OH
70.4 35.8 25.1 26.3
65.5 33.2 20.5 27.1
–OCH 3
79.2 32.2 24.5 26.4
74.9 30.0 21.1 26.6
–OCOCH 3
72.3 32.2 24.4 26.1
–OCO–phenyl
72.8 31.5 24.1 24.7
69.0 29.3 20.3 24.7
–OSi(CH 3 ) 3
70.5 36.0 24.7 25.0
66.1 33.1 19.8 25.0
–NH 2
51.1 37.6 25.8 26.3
47.4 33.8 20.0 27.1
–NHCH 3
58.7 32.7 25.7 26.8
–N(CH 3 ) 2
64.3 29.2 26.5 26.9
–NH 3
+ Cl –
51.8 32.2 24.8 25.2
–N=C=N–cyclohexyl 55.7 35.0 24.8 25.5
–NO 2
84.6 31.4 24.7 25.5
–N 3
59.5 31.5 24.5 24.5
56.8 29.0 20.1 25.2
–C– – – N
28.0 29.6 24.6 25.1
26.4 27.4 21.9 25.0
–NC
51.9 33.7 24.4 25.2
50.3 30.5 20.1 25.2
–NCS
55.3 33.9 24.5 24.8
52.8 31.3 20.4 24.8
–SH
38.3 38.1 26.6 25.3
35.9 33.1 19.4 25.7
–CHO
50.1 26.0 25.2 26.1
46.4 24.7 22.7 27.1
–COCH 3
51.5 29.0 26.6 26.3
–COOH
43.7 29.6 26.2 26.6
–COO –
47.2 30.9 26.9 26.9
–COOCH 3
43.4 29.6 26.0 26.4
39.1 27.7 24.1 26.7
–COCl
55.4 29.7 25.5 25.9
R
R
a
a
b
b
c
c
d
d
C
X
O
N
S
O
||
C
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.4 Alicyclics
95
13 C Chemical Shifts of Equatorially and Axially Monosubstituted Cyclohexanes
(δ in ppm)
Substituent R
a
b
c
d
a
b
c
d
–H
27.1 27.1 27.1 27.1
27.1 27.1 27.1 27.1
–CH 3
33.2 36.0 27.1 27.0
28.4 32.4 20.6 26.9
–CH 2 CH 3
40.1 33.4 26.9 27.2
35.5 30.0 21.4 27.1
–CH 2 CH 2 CH 3
40.0 33.6 26.6 26.9
–CH(CH 3 ) 2
44.6 30.0 26.8 27.3
41.1 30.2 21.6 27.1
–CH 2 CH 2 CH 2 CH 3
38.4 34.1 27.1 27.3
–C(CH 3 ) 3
48.8 28.1 27.7 27.1
–cyclohexyl
44.3 30.8 27.4 27.4
–CH=CH 2
42.1 32.3 26.0 27.1
37.0 30.0 21.2 27.1
–C– – – CH
28.7 32.1 25.2 24.4
28.0 30.0 21.2 25.7
–phenyl
45.1 34.9 27.4 26.7
35.2 30.1 21.9 27.7
–F
91.0 32.8 23.6 25.3
88.1 30.1 19.8 25.0
–Cl
59.8 37.4 26.1 25.4
60.1 33.9 20.4 26.0
–Br
52.4 38.3 27.3 25.6
55.4 34.9 21.5 26.4
–I
31.2 40.1 28.3 25.4
38.3 36.0 22.8 26.1
–OH
70.4 35.8 25.1 26.3
65.5 33.2 20.5 27.1
–OCH 3
79.2 32.2 24.5 26.4
74.9 30.0 21.1 26.6
–OCOCH 3
72.3 32.2 24.4 26.1
–OCO–phenyl
72.8 31.5 24.1 24.7
69.0 29.3 20.3 24.7
–OSi(CH 3 ) 3
70.5 36.0 24.7 25.0
66.1 33.1 19.8 25.0
–NH 2
51.1 37.6 25.8 26.3
47.4 33.8 20.0 27.1
–NHCH 3
58.7 32.7 25.7 26.8
–N(CH 3 ) 2
64.3 29.2 26.5 26.9
–NH 3
+ Cl –
51.8 32.2 24.8 25.2
–N=C=N–cyclohexyl 55.7 35.0 24.8 25.5
–NO 2
84.6 31.4 24.7 25.5
–N 3
59.5 31.5 24.5 24.5
56.8 29.0 20.1 25.2
–C– – – N
28.0 29.6 24.6 25.1
26.4 27.4 21.9 25.0
–NC
51.9 33.7 24.4 25.2
50.3 30.5 20.1 25.2
–NCS
55.3 33.9 24.5 24.8
52.8 31.3 20.4 24.8
–SH
38.3 38.1 26.6 25.3
35.9 33.1 19.4 25.7
–CHO
50.1 26.0 25.2 26.1
46.4 24.7 22.7 27.1
–COCH 3
51.5 29.0 26.6 26.3
–COOH
43.7 29.6 26.2 26.6
–COO –
47.2 30.9 26.9 26.9
–COOCH 3
43.4 29.6 26.0 26.4
39.1 27.7 24.1 26.7
–COCl
55.4 29.7 25.5 25.9
R
R
a
a
b
b
c
c
d
d
C
X
O
N
S
O
||
C