N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.4 Alicyclics
93
4.4 Alicyclics
4.4.1 Chemical Shifts
Saturated Monocyclic Alicyclics (δ in ppm)
13 C Chemical Shifts of Monosubstituted Cyclopropanes (δ in ppm)
Substituent R
a
b
other
–H
-2.8
-2.8
–CH 3
4.9
5.6
CH 3 19.4
–CH 2 CH 3
12.8
4.1
CH 2 27.8, CH 3 13.6
–CH 2 CH 2 CH 2 CH 3
10.9
4.4
1-CH 2 34.7, 2-CH 2 32.0
–C(CH 3 ) 3
22.7
0.3
C 29.3, CH 3 28.2
–CH 2 Cl
13.6
5.5
CH 2 50.3
–CH 2 OH
12.7
2.2
CH 2 66.5
–CH=CH 2
14.7
6.6
CH 142.4, CH 2 111.5
–phenyl
15.3
9.2
C 143.9, CH 125.3–128.2
–Cl
27.3
8.9
–Br
14.2
9.1
–I
-20.1
10.4
–OH
45.7
6.8
–NH 2
24.0
7.4
–NO 2
54.3
11.7
–C– – – N
-4.5
6.2
CN 121.5
–CHO
22.7
7.4
CO 202.1
–COCH 3
20.1
9.6
CO 207.3, CH 3 29.1
–CO–phenyl
17.1
11.5
–COOH
12.7
8.9
CO 181.6
–COOCH 3
12.2
7.7
CO 174.7, CH 3 51.1
-2.8
25.6
26.8
27.1
28.8
22.9
n
δ
9
26.0
10
25.1
11
26.3
12
23.8
13
26.2
14
25.2
15
27.0
20
28.0
30
29.3
40
29.4
72
29.7
R
a
b
C
X
O
N
O
||
C
(CH 2 ) n