COMMON POLAR APROTIC SOLVENTS

Aprotic solvents with moderately higher dielectric constants than nonpolar solvents
(between 5 and 20) make adequate general-purpose solvents for a wide range of
reactions. Aprotic solvents with dielectric constants greater than 20 and large dipole
moments can dissolve charged species such as various anions used as nucleophiles.
Without hydrogen bonding in the solvent, these nucleophiles are relatively free in
solution, making them more reactive.

Dielectric Dipole Boiling

Solvent Structure
Constant Moment Point (°C)

O
••
••

Dimethylsulfoxide
46.68 3.96 189
(DMSO) H3C S CH3
• •

O
••
••

Dimethylformamide • •
H C N CH3 36.71 3.86 153
(DMF)
CH3

H
Acetonitrile H C C N 38.8 3.92 81.6
• •

(MeCN)
H

CH3

N CH3
• •

Hexamethylphosphoric
30.0 5.54 233
acid (HMPA) H3C
• •
N P N
• •
CH3

CH3 O CH3
••
••

O
••
••

Acetone 20.7 2.88 56

H3C C CH3

H
• • • •
Dichloromethane Cl C Cl 8.93 1.60 39.6
• •

• •

• • • •

O
••
••

Tetrahydrofuran 7.58 1.75 66

(THF)

O
••
••

Methyl acetate 6.7 1.69 57

• •
H3C OCH
• • 3

O
••
••

Ethyl acetate 6.02 1.78 77.1

• •
H3C OCH
• • 2CH3