pKa Values of Selected Compounds

In structures with more than one proton type, proton corresponding to given pKa is in bold. Values in parentheses are alternate pKa values given by some sources.

Inorganic (Mineral) Acids HSbF6 < -12 HClO4 -10 HI -10 H2SO4 pKa1 = -9 (-5); pKa2 = 2.0 HBr -9 (-5.8) HCl -7 (-3.9) HNO3 -1.3 H3PO4 pKa1 = 2.1; pKa2 = 7.2; pKa3 = 12.3 HF 3.2 H2O 15.7 Oxonium Ions (R3O+)
O H
O H
H

OCH3

OH

-8

-7.3

-6.5

-6.1

(CH3)2 OH

(CH3CH2)2 OH

CH3OH2

CH3CH2OH2

-3.8

-3.6
H

-2.5

-2.4

H3O

NH2

-1.7 Carboxylic Acids (RCO2H)

CF3CO2H

0.0
Cl3CCO2H HO2C-CO2H Cl2CHCO2H

0.2
CO2H CO2H

0.64

pKa1 = 1.2; pKa2 = 4.2

1.3

H3N

CO2H

FCH2CO2H

ClCH2CO2H

pKa1 = 1.9; pKa2 = 6.1

2.2

2.7

2.8

Lecture Supplement: pKa Values of Selected Compounds

15

Cl CO2H

OH

CO2H

BrCH2CO2H
CO2H CO2H

2.83

2.9
CO2H

2.9

pKa1 = 2.9; pKa2 = 5.4

HO2CH2CO2H
HO2 C

ICH2CO2H

O2N

CO2H

pKa1 = 2.9; pKa2 = 5.7

O O CO2H CH3

pKa1 = 3.0; pKa2 = 4.4

3.2

3.4

HO2 C

CO2H

HCO2H

HO2 C

CO2H

3.5

pKa1 = 3.5; pKa2 = 4.6

pKa1 = 3.5; pKa2 = 4.8

3.7

ClCH2CH2CO2H

Br

CO2H

CO2H

HO2C(CH2)2CO2H

3.98

4.0

4.2

pKa1 = 4.2; pKa2 = 5.6

HO2C(CH2)3CO2H

H3C

CO2H

H3CO

CO2H

CH3CO2H

pKa1 = 4.3; pKa2 = 5.4

CH3(CH2)8CO2H

4.3
CH3(CH2)6CO2H

4.5
CH3(CH2)14CO2H

4.78
H2CO3

4.84 Phenols (ArOH)

NO2 O2N NO2 OH
O2N

4.89

6.5

pKa1 = 6.5; pKa2 = 10.2

NO2 OH

NO2 OH

O2N

OH

0.78
Cl OH

4.0

7.2

7.2

Cl
O2N OH
Cl OH

OH

8.1 16

8.3

8.8

9.3

Lecture Supplement: pKa Values of Selected Compounds

OH
OH

OH
H3C OH

9.3

9.6
CH3

10.0

10.1

H3C

OH

OH

H2N

OH

10.2

10.2

10.3

Aminium (R3NH+) and Iminium (R2C=NH+) Ions

H N H
O2N NH3 Br NH3

Cl

NH3

0.80

1.0
H
NH3

3.9

4.0
H

N H

CH3

N
N H

CH3

CH3

4.6

4.7

4.9

5.06
H3C H

H3C

NH3

H3CO

NH3

5.1

5.2

5.3

5.5

HO

NH3

HN

NH

H3 N

CO2CH3

NH2

6.0

6.8

7.75

8.0

H2N

NH3

NH2

CH2NH3

NH4

8.1

9.3

9.3

9.4

HOCH2 CH2 NH3

O2CCH2NH3

(CH3)3 NH

NH3

9.5

9.7

9.8

10.45 17

Lecture Supplement: pKa Values of Selected Compounds

NH3

NH3

NH3

(CH3CH2CH2 )3NH

10.49

10.56

10.61

10.64

CH3NH3

NH3

NH3

NH3

10.65

10.67

10.67

10.73

CH3CH2NH3

(CH3CH2)2 NH2

(CH3CH2CH2 )2NH2

NH2

10.76

10.98

10.98

11.15

NH2

11.2 Alcohols (ROH)

O O OH

CF3CH2OH

HC

CCH2OH

(CH3)3 NCH2CH2 OH

8.2

12.4

13.5

13.9

CH3OH

H2O

CH3CH2OH

OH

15.5

15.7

16 - 17

17

OH

OH

18

18 - 19

Carbonyl Compounds: -Deprotonation to Form Enolate

O O H H H
H H O O

O OCH2 CH3
CH3CH2O

O OCH2 CH3

5.9

9.0

11.0

13.3

18

Lecture Supplement: pKa Values of Selected Compounds

O H H

O Ph CH3 H3 C

O H
H3C

O CH3

15.5
O OCH3 H H

15.9
O H3 C OCH2 CH3 H3 C

17
O N(CH3 )2

19 - 20

22 Amides (O=C-N-H)
O

23 - 24.5

30

O
NH O

NH2

9 Amines (R2N-H)
N N N N H

15 - 16
N

NH
N H

NH

8.9
H N

14.4

17

36

NH3

CH3NH2

36
O F3C S O OH

36 - 38
O S O OH

40
O
CH3SH2

Sulfur and Selenium Compounds

H3C S O OH

-16
H2Se

-6.5 to 0.6
H2S

-6.8
SH

-1.2
CH3CH2SH

3.89

7.0
S H H
H3C

7.8
O S CH3

10.5

CH3SH

10.7

31

31.3 19

Lecture Supplement: pKa Values of Selected Compounds

Hydrocarbons (R3C-H)
H H
H H

H
H H

15 16

20

23

25 - 26

Ph3CH

H2C

CH2

CH3

33

36 - 45

39 - 46

41

H2C

CHCH3

CH4

CH3CH3

43 Miscellaneous Compounds
H N H H

43
O CH3CH 2 N O

49 - 60

50 - 62
O

H3C

N O

-3.8

8.6

9.1

10.2

H3C

CHCl3

H2

25

25

35

20

Lecture Supplement: pKa Values of Selected Compounds