Group

pKas: Table of Data

Acid Dissociation Reaction
O N

pKa

Strongest Acid protonated nitro group protonated nitrile (nitrilium) protonated ketone protonated thiol (sulfonium)
O H H

Weakest Base
+ O N O

11.3

sp N+

CH3 C N H H CH3
sp2 O+

+ CH3 C N

10.1

O C

+ CH3

CH3 H
sp3 S+

O C

CH3

7.2

CH3 S

CH3 S

6.8
H

Group protonated phenol (oxonium)

H CH3

Acid Dissociation Reaction

H O H O H + H

pKa 6.7

protonated ester

O C

H OCH2CH3

+ CH3

O C

OCH2CH3

6.5

Why is carbonyl oxygen more basic?

(HCl) = 6.2
H + CH3 O C

protonated carboxylic acid protonated sulfide (sulfonium)

H CH 3

O C

OH

OH

6.1

CH3 S

CH3 H

CH3 S

CH3

5.4

Group protonated ether protonated alcohol protonated amide (amidinium) carboxylic acid (e deficient) phosphoric acid
CH3CH2

Acid Dissociation Reaction

C H2CH3 O H H O H H + CH3CH2 C H2CH3 O H O

pKa 3.6

CH3 CH2 H CH3

+ CH3 CH2

2.4

O C

H NH2

+ CH3

O C

NH2

CF 3

O C

+ CF3

O C

0.2
O

O H HO P O OH

O HO P O OH

2.1

Group anilinium

Acid Dissociation Reaction

H H N H H + H N

pKa 4.6

carboxylic acid

CH 3

O C H N

+ CH3

O C

4.7
O

pyridinium
H

5.3
CH3 CH3

iminium
CH3

N C H N

CH3 H CH3 H H + + CH3

N C H N N

5.5

imidazolium

7.0

Group phosphoric acid (monobasic)

Acid Dissociation Reaction

O HO P O O H O C O C H O + HO P O O + CH3 CH2 O C O C

pKa 7.2

!-keto CH3CH2 S thioester 1,3diketone

H CH3

8.5
CH3

C H

H H O C H CH3 + CH3 O C

CH3

O C

H H

C H

O C

CH3

9.0

ammonium

CH3

CH3 N H CH3 O

CH3

CH3 N CH3 O

9.8

phenol

10.0

Group thiol

Acid Dissociation Reaction

CH3 CH2 O C S H H H CH3 + CH3CH2 O C S

pKa 10.5
O C

!-ketoCH3CH2 ester O

O C

+ CH3 CH2

H H

C H

CH3

11.0

iminium (C-H acid)

CH3 CH3 H

N C

CH3 H C H H H +

CH3 CH3

N C

CH3 C H H

11.0

phosphate (dibasic)

O O P O O N C H N H H

O O P O O H N C

12.4

guanidinium

CH3

N H

+ CH 3

N H

N H

13.2

Group imidazole

Acid Dissociation Reaction

H N N H + N N O C

pKa 14.4

amide
CH3

O C

N H O

+ CH3

15.0
N H O

alcohol

CH3CH2 O C

CH3CH2 O C

15.9

ketone

H C H H H

H CH3

C H

CH3

20

ester

C H H

O C

H OCH2CH3

C H

O C

OCH 2CH3

24.5

Group terminal alkyne

Acid Dissociation Reaction

H C C H H + H C C

pKa 25

nitrile (" C-H)

H H C C N H

H C C N H

25

amine

CH 3

H N H

CH3 N H

35

benzylic C-H

H H C H

H C H +

41

Group
H H

Acid Dissociation Reaction

H H H H H H + H H H H

pKa

benzene

43

vinyl hydrogen

H H C C H H

H C C H H

44

alkane hydrogen

CH3

H C H H

CH3

H C H

50

Weakest Acid

Strongest Base