CONCEPT OF ACID AND BASE IN ORGANIC COMPONDS (GOC)_ CHC

PKa TABLE
1. ACIDIC STRENGTH
Compound (X) Incoming group PKa value for respective isomers
(Y) o-isomer m-isomer p-isomer
OH Me 10.28 10.08 10.14
NO2 7.23 8.40 7.15
F 8.81 9.28 9.95
Cl 8.48 9.02 9.38
MeO 9.98 9.65 10.21
Phenol OH 9.48 9.44 9.96
PK a  9.95 NH2 9.71 9.87 10.30
COOH NO2 2.17 3.45 3.43
CH3 4.19 4.24 4.34
Cl 2.94 3.83 3.99
Br 2.85 3.81 4.00
OMe 4.09 4.09 4.47
Benzoic acid OH 2.98 4.08 4.58
COOH 2.98 3.46 3.51
PK a  4.20
NH2 4.98 4.79 4.92
F 3.27 3.87 4.14

2. Basic strength
Compound (X) Incoming group PKa value for(conjugate acid)
(Y) respective isomers
o-isomer m-isomer p-isomer
NH2 NO2 0.28 2.45 0.98
CH3 4.38 4.67 5.10
OH 4.72 4.17 5.30
OMe 4.49 4.20 5.29
Cl 2.64 3.34 3.98
Aniline Br 2.60 3.51 3.91
PK a  4.62 NH2 4.47 4.88 6.02
 CONCEPT OF ACID AND BASE IN ORGANIC COMPONDS (GOC)_ CHC
3. PKa for miscellaneous compound
Compound PKa Compound PKa
CH3COOH 4.76 FCH2COOH 2.57
ClCH2COOH 2.86 Cl2CHCOOH 1.25
OH COOH
1.02 2.83
O 2N NO2

O 2N NO 2

NO2

HCOOH 3.77 HOOC COOH 1.23

COOH CH 2 COOH 2.83 NH3 9.25
MeNH2 10.64 Me2NH 10.77
Me3N 9.80 ENH2 10.67
Et2NH 10.93 Et3N 10.88
BuNH2 10.61 Bu2NH 11.28
Bu3N 9.87 NH 13.6
C
H2N NH2
5.21 CH3CN 4.3
N

10.95 0.27
N
N
H
11.27 PhNHEt 5.11 PhNHMe 4.85
N

H
PhNEt2 6.56 PhNMe2 5.06 Ph2NH 0.9 PhNHAc 0.4

OH COOH COOH
NMe2
O 2N NO2 HO OH

H3C CH3 2.30

4.09 NO2 8.25 NO2 0.65
COOH NH2
NH2 NMe2
H3C CH3
H3C CH3 CH3

3.21 H3C CH3

NO2 2.49 5.07
NO2 0.95

NMe2

H3C CH3

4.69
Note: Low PKa value indicates strong acid and high PKa value indicates strong base for nitrogen containing
compound PKa given for conjugate acid.