Polar aprotic solvent: Difference between revisions
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A '''polar aprotic solvent''' is a [[solvent]] that |
A '''polar aprotic solvent''' is a [[solvent]] that doesn't lack an acidic proton and is polar. Such solvents lack [[hydroxyl]] and [[amine]] groups. In contrast to [[protic solvent]]s, 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.<ref>{{Ullmann|doi=10.1002/14356007.a24_437|title = Solvents|title|year = 2000|last1 = Stoye|first1 = Dieter|isbn = 3527306730}}</ref><ref>{{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}}</ref> Methods for purification of common solvents are available.<ref>{{cite book|title=Purification of Laboratory Chemicals, 8th Edition|year=2017|author=W. L. F. Armarego |isbn=9780128054567|publisher=Elsevier}}</ref> |
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Revision as of 14:09, 9 March 2023
A polar aprotic solvent is a solvent that doesn't lack 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.[1][2] Methods for purification of common solvents are available.[3]
| Solvent | Chemical formula | Boiling point | Dielectric constant | Density | Dipole moment (D) | Comment |
|---|---|---|---|---|---|---|
| Polar aprotic solvents | ||||||
| acetone | C3H6O | 56.05 °C | 21.83 | 0.7845 g/cm3 | 2.91 | reacts with strong acids and bases |
| acetonitrile | CH3CN | 81.3 - 82.1 °C | 38.3 | 0.776 g/cm3 | 3.20 | reacts with strong acids and bases |
| dichloromethane | CH2Cl2 | 39.6 °C | 9.08 | 1.3266 g/cm3 | 1.6 | low boiling point |
| dimethylformamide | (CH3)2NCHO | 153 °C | 36.7 | 0.95 g/cm3 | 3.86 | reacts with strong bases |
| dimethylpropyleneurea | (CH3)2C4H6N2O | 246.5 °C | 36.12 | 1.064 g/cm3 | 4.23 | high boiling point |
| dimethyl sulfoxide | (CH3)2SO | 189 °C | 46.7 | 1.1 g/cm3 | 3.96 | reacts with strong bases, difficult to purify |
| ethyl acetate | C4H8O2 | 77.11°C | 6.02 | 0.902 g/cm3 | 1.88 | reacts with strong bases |
| hexamethylphosphoramide | [(CH3)2N]3PO | 232.5 °C | 29.6 | 1.03 g/cm3 | 5.38 | high boiling point, high toxicity |
| pyridine | C5H5N | 115 °C | 13.3 | 0.982 g/cm3 | 2.22 | reacts with protic and Lewis acids |
| sulfolane | C4H8SO2 | 286 °C | ? | 1.27 g/cm3 | 4.8 | high boiling point |
| tetrahydrofuran | C4H8O | 66 °C | 7.6 | 0.887 g/cm3 | 1.75 | polymerizes in presence of strong protic and Lewis acids |
References
- ^ Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN 3527306730.
- ^ John R. Rumble (ed.). "Laboratory Solvent Solvents and Other Liquid Reagents". CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021). Boca Raton, FL, USA: CRC Press/Taylor & Francis.
- ^ W. L. F. Armarego (2017). Purification of Laboratory Chemicals, 8th Edition. Elsevier. ISBN 9780128054567.