N
X
C
O
N
S
Hal
Solvents
Natural
Products
P Si
C
C
C C
C
C
102
4 13 C NMR
Substituent R
Z 1
Z 2
Z 3
Z 4
–S(O) 2 F
4.6
0.0
1.5
7.5
–S(O) 2 Cl
15.6
-1.7
1.2
6.8
–S(O) 2 NH 2
10.8
-3.0
0.3
3.2
–SCN
-3.7
2.5
2.2
2.2
–CHO
8.2
1.2
0.5
5.8
–COCH 3
8.9
0.1
-0.1
4.4
–COCF 3
-5.6
1.8
0.7
6.7
–COC– – – CH
7.4
1.0
0.0
5.9
–CO–phenyl
9.3
1.6
-0.3
3.7
–COOH
2.1
1.6
-0.1
5.2
–COONa
9.7
4.6
2.2
4.6
–COOCH 3
2.0
1.2
-0.1
4.3
–CONH 2
5.0
-1.2
0.1
3.4
–CON(CH 3 ) 2
6.0
-1.5
-0.2
1.0
–COCl
4.7
2.7
0.3
6.6
–COSH
6.2
-0.6
0.2
5.4
–CH=NCH 3
8.8
0.5
0.1
2.3
–CS–phenyl
18.7
1.0
-0.6
2.4
–P(CH 3 ) 2
13.6
1.6
-0.6
-1.0
–P(phenyl) 2
8.9
5.2
0.0
0.1
–P + (phenyl) 2 CH 3
-9.7
5.2
2.0
6.7
–PO(CH 3 ) 2
2.5
1.1
0.1
3.0
–PO(phenyl) 2
5.8
3.9
-0.1
3.0
–PO(OH) 2
-1.9
3.6
1.5
5.6
–PO(OCH 2 CH 3 ) 2
1.6
3.6
-0.2
3.4
–PS(CH 3 ) 2
6.7
2.0
0.2
2.9
–PS(OCH 2 CH 3 ) 2
6.1
2.8
-0.4
3.4
–Li
-43.2
-12.7
2.4
3.1
–MgBr
-35.8
-11.4
2.7
4.0
–SiH 3
-0.5
7.3
-0.4
1.3
–SiH 2 CH 3
4.8
6.3
-0.5
1.0
–Si(CH 3 ) 3
11.6
4.9
-0.7
0.4
–Si(phenyl) 3
5.8
7.9
-0.6
1.1
–SiCl 3
3.0
4.6
0.1
4.2
–Ge(CH 3 ) 3
13.7
4.5
-0.5
-0.2
–Sn(CH 3 ) 3
13.2
7.2
-0.4
-0.4
–Pb(CH 3 ) 3
20.1
8.0
-0.1
-1.0
–AsH 2
1.7
7.9
0.8
0.0
–As(phenyl) 2
11.1
5.0
0.1
-0.1
–As(O)(OH) 2
3.8
1.6
0.8
4.5
–SeCH=CH 2
0.7
4.7
0.4
-1.4
–SeCN
-5.3
5.1
2.9
2.1
–Sb(phenyl) 2
9.8
7.7
0.3
0.0
–Hg–phenyl
41.6
9.3
-0.9
-1.6
–HgCl
22.5
8.0
-0.6
-0.9
S
O
||
C
P
M