N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.5 Aromatic Hydrocarbons
101
Substituent R
Z 1
Z 2
Z 3
Z 4
–F
33.6
-13.0
1.6
-4.4
–Cl
5.3
0.4
1.4
-1.9
–Br
-5.4
3.3
2.2
-1.0
–I
-31.2
8.9
1.6
-1.1
–OH
28.8
-12.8
1.4
-7.4
–ONa
39.6
-8.2
1.9
-13.6
–OCH 3
33.5
-14.4
1.0
-7.7
–OCH=CH 2
28.2
-11.5
0.7
-5.8
–O–phenyl
27.6
-11.2
-0.3
-6.9
–OCOCH 3
22.4
-7.1
0.4
-3.2
–OSi(CH 3 ) 3
26.8
-8.4
0.9
-7.1
–OPO(O–phenyl) 2
21.9
-8.4
1.2
-3.0
–OCN
25.0
-12.7
2.6
-1.0
–NH 2
18.2
-13.4
0.8
-10.0
–NHCH 3
15.0
-16.2
0.8
-11.6
–N(CH 3 ) 2
16.0
-15.4
0.9
-10.5
–NH–phenyl
14.7
-10.6
0.9
-10.5
–N(phenyl) 2
13.1
-7.0
0.9
-5.6
–NH 3
+
0.1
-5.8
2.2
2.2
–NH 2
+ CH(CH 3 ) 2
5.5
-4.1
1.1
0.7
–N + (CH 3 ) 3
19.5
-7.3
2.5
2.4
–N(O)(CH 3 ) 2
26.2
-8.4
0.8
0.6
–NHCOCH 3
9.7
-8.1
0.2
-4.4
–NHOH
21.5
-13.1
-2.2
-5.3
–NHNH 2
22.8
-16.5
0.5
-9.6
–N=CH–phenyl
24.7
-6.5
1.3
-1.5
–N=NCH 3
22.2
-6.2
0.5
-3.0
–NO
37.4
-7.6
0.8
7.1
–NO 2
19.9
-4.9
0.9
6.1
–C– – – N
-16.0
3.5
0.7
4.3
–NC
-1.8
-2.2
1.4
0.9
–NCO
5.1
-3.7
1.1
-2.8
–NCS
3.0
-2.7
1.3
-1.0
–N + – – – N
-12.7
6.0
5.7
16.0
–SH
4.0
0.7
0.3
-3.2
–SCH 3
10.0
-1.9
0.2
-3.6
–SC(CH 3 ) 3
4.5
9.0
-0.3
0.0
–S(CH 3 ) 2
+
-1.0
3.1
2.2
6.3
–SCH=CH 2
5.8
2.0
0.2
-1.8
–S–phenyl
7.3
2.5
0.6
-1.5
–S–S–phenyl
7.5
-1.3
0.8
-1.1
–S(O)CH 3
17.6
-5.0
1.1
2.4
–S(O) 2 CH 3
12.3
-1.4
0.8
5.1
–S(O) 2 OH
15.0
-2.2
1.3
3.8
–S(O) 2 OCH 3
6.4
-0.6
1.5
5.9
X
O
N
S