Polar aprotic solvent

{{Short description|Polar solvent with a low tendency to donate hydrogen ions}}

A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. In contrast to protic solvents, these solvents do not serve as proton donors in hydrogen bonding, although they can be proton acceptors. Many solvents, including chlorocarbons and hydrocarbons, are classifiable as aprotic, but polar aprotic solvents are of particular interest for their ability to dissolve salts.{{Ullmann|doi=10.1002/14356007.a24_437|title = Solvents|title|year = 2000|last1 = Stoye|first1 = Dieter|isbn = 3527306730}}{{cite book|chapter=Laboratory Solvent Solvents and Other Liquid Reagents|title=CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021)|editor=John R. Rumble|publisher=CRC Press/Taylor & Francis|location=Boca Raton, FL, USA}} Methods for purification of common solvents are available.{{cite book|title=Purification of Laboratory Chemicals, 8th Edition|year=2017|author=W. L. F. Armarego |isbn=9780128054567|publisher=Elsevier}}

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! Solvent

! Chemical formula

! Boiling point

! Dielectric constant

! Density

! Dipole moment (D)

! Comment

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| colspan="7" | Polar aprotic solvents

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| acetone

|(CH₃)₂CO

|56.1 °C

| 21.8

|0.785 g/cm³

|2.91

|reacts with strong acids and bases

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| acetonitrile

| CH₃CN

| 82 °C

| 38.3

|0.776 g/cm³

| 3.20

|reacts with strong acids and bases

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| dichloromethane

|CH₂Cl₂

|39.6 °C

|9.08

|1.327 g/cm³

|1.6

|low boiling point

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| dimethylacetamide

| (CH₃)₂NCOCH₃

| 165 °C

|37.8

| 0.94 g/cm³

| 3.72

|reacts with strong acids and bases

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| dimethylformamide

| (CH₃)₂NCHO

| 153 °C

|36.7

| 0.95 g/cm³

| 3.86

|reacts with strong acids and bases

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| N-methylpyrrolidone

|CH₃NCOC₃H₆

|203 °C

|32.3

|1.028 g/cm³

|4.09

|high boiling point

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| dimethylimidazolidone

|(CH₃N)₂COC₂H₄

|225 °C

|37.6

|1.056 g/cm³

|4.09

|high boiling point

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| dimethylpropyleneurea

|(CH₃N)₂COC₃H₆

|246.5 °C

|36.1

|1.064 g/cm³

|4.23

|high boiling point

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| dimethyl sulfoxide

| (CH₃)₂SO

| 189 °C

| 46.7

| 1.10 g/cm³

| 3.96

|reacts with strong bases, difficult to purify

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| ethyl acetate

|C₂H₅OCOCH₃

|77.1°C

|6.02

|0.902 g/cm³

|1.88

|reacts with strong bases

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| hexamethylphosphoramide

|[(CH₃)₂N]₃PO

|232.5 °C

|29.6

|1.03 g/cm³

|5.38

high boiling point, high toxicity

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| propylene carbonate

| CH₃C₂H₃O₂CO

| 242 °C

| 64.9

| 1.205 g/cm³

| 4.94

|high boiling point

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| pyridine

| C₅H₅N

| 115 °C

| 13.3

| 0.982 g/cm³

| 2.22

| reacts with protic and Lewis acids

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| sulfolane

| C₄H₈SO₂

| 286 °C

| 43.3

| 1.27 g/cm³

| 4.8

| high boiling point

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| tetrahydrofuran

| C₄H₈O

| 66 °C

| 7.6

| 0.887 g/cm³

| 1.75

|polymerizes in presence of strong protic and Lewis acids

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References

{{Cite journal |last=Pfennig |first=A. |date=1995 |title=Kirk‐Othmer Encyclopedia of Chemical Technology, 4th Ed., Vol. 10. M. Howe‐Grant (Editor). John Wiley & Sons, New York 1993. 1022 S. mit zahir. Abb. und Tab., geb., £ 185.00 |url=https://doi.org/10.1002/cite.330670323 |journal=Chemie Ingenieur Technik |volume=67 |issue=3 |pages=352–353 |doi=10.1002/cite.330670323 |issn=0009-286X|url-access=subscription }}

Category:Solvents