N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
94
4 13 C NMR
13 C Chemical Shifts of Monosubstituted Cyclopentanes (δ in ppm)
Substituent R
a
b
c other
–H
26.0
26.0
26.0
–CH 3
34.8
34.8
25.4 CH 3 21.4
–CH 2 CH 3
42.3
32.6
25.4 CH 2 29.2, CH 3 13.2
–CH(CH 3 ) 2
47.4
30.0
24.7 CH 33.9, CH 3 21.7
–C(CH 3 ) 3
50.3
26.5
25.1 C 32.5, CH 3 27.6
–CH 2 OH
41.2
28.3
24.5 CH 2 67.0
–F
95.5
32.8
22.5 1 J CF 173.5, 2 J CF 22.1, 3 J CF <1.5 Hz
–Cl
62.0
37.2
23.1
–Br
53.5
37.9
23.3
–I
28.7
40.7
24.9
–OH
73.7
35.4
23.4
–OCH 3
82.2
31.4
23.1 CH 3 56.0
–OCOCH 3
77.7
33.8
24.9 CO 170.8, CH 3 21.7
–NH 2
53.4
36.4
24.0
–NO 2
87.0
32.6
24.8
–C– – – N
27.0
30.5
24.2 CN 123.4
–SH
38.3
37.7
24.6
–CO–phenyl
46.4
30.0
26.3
–COOH
43.0
29.2
25.1 CO 183.8
–COOCH 3
43.7
30.0
25.8 CO 177.0, CH 3 51.4
R
a
b
c
C
X
O
N
S
O
||
C