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{{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 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>
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 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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! [[Density]]
! [[Density]]
! [[Bond dipole moment|Dipole moment]] ([[Debye|D]])
! [[Bond dipole moment|Dipole moment]] ([[Debye|D]])
! Comment

<!-- ### Non-polar solvents ### -->
<!-- ### Non-polar solvents ### -->


<!-- ### Polar aprotic solvents ### -->
<!-- ### Polar aprotic solvents ### -->
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| colspan="6" | '''[[Chemical polarity|Polar]] aprotic solvents'''
| colspan="7" | '''[[Chemical polarity|Polar]] aprotic solvents'''
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[acetone]]
| [[acetone]]
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|0.7845 g/cm<sup>3</sup>
|0.7845 g/cm<sup>3</sup>
|2.91
|2.91
|reacts with strong acids and bases
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[acetonitrile ]]
| [[acetonitrile ]]
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|0.776 g/cm<sup>3</sup>
|0.776 g/cm<sup>3</sup>
| 3.20
| 3.20
|reacts with strong acids and bases
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[dichloromethane]]
| [[dichloromethane]]
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|1.3266 g/cm<sup>3</sup>
|1.3266 g/cm<sup>3</sup>
|1.6
|1.6
|low boiling point
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[dimethylformamide]]
| [[dimethylformamide]]
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| 0.95 g/cm<sup>3</sup>
| 0.95 g/cm<sup>3</sup>
| 3.86
| 3.86
|reacts with strong bases
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[DMPU|dimethylpropyleneurea]]
| [[DMPU|dimethylpropyleneurea]]
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|1.064 g/cm<sup>3</sup>
|1.064 g/cm<sup>3</sup>
|4.23
|4.23
|high boiling point
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[dimethylsulfoxide]]
| [[dimethyl sulfoxide]]
| (CH<sub>3</sub>)<sub>2</sub>SO
| (CH<sub>3</sub>)<sub>2</sub>SO
| 189 °C
| 189 °C
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| 1.1 g/cm<sup>3</sup>
| 1.1 g/cm<sup>3</sup>
| 3.96
| 3.96
|reacts with strong bases, difficult to purify
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[ethyl acetate]]
| [[ethyl acetate]]
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|0.902 g/cm<sup>3</sup>
|0.902 g/cm<sup>3</sup>
|1.88
|1.88
|reacts with strong bases
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[hexamethylphosphoramide]]
| [[hexamethylphosphoric triamide]]
|[(CH<sub>3</sub>)<sub>2</sub>N]<sub>3</sub>PO
|[(CH<sub>3</sub>)<sub>2</sub>N]<sub>3</sub>PO
|232.5 °C
|232.5 °C
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|1.03 g/cm<sup>3</sup>
|1.03 g/cm<sup>3</sup>
|5.38
|5.38
|| high boiling point, high toxicity
|- bgcolor="#FFEEEE"
| [[pyridine]]
| C<sub>5</sub>H<sub>5</sub>N
| 115 °C
| 13.3
| 0.982 g/cm<sup>3</sup>
| 2.22
| reacts with protic and Lewis acids
|- bgcolor="#FFEEEE"
| [[sulfolane]]
| C<sub>4</sub>H<sub>8</sub>SO<sub>2</sub>
| 286 °C
| ?
| 1.27 g/cm<sup>3</sup>
| 4.8
| high boiling point
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
| [[tetrahydrofuran]]
| [[tetrahydrofuran]]
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| 0.887 g/cm<sup>3</sup>
| 0.887 g/cm<sup>3</sup>
| 1.75
| 1.75
|polymerizes in presence of strong protic and Lewis acids
|- bgcolor="#FFEEEE"
|- bgcolor="#FFEEEE"
|}
|}
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|-
|-
|}
|}



== References ==
== References ==

Latest revision as of 17:22, 13 October 2023

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.[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

[edit]
  1. ^ Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN 3527306730.
  2. ^ 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.
  3. ^ W. L. F. Armarego (2017). Purification of Laboratory Chemicals, 8th Edition. Elsevier. ISBN 9780128054567.
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