Protic solvent

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In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group) or a nitrogen (as in an amine group). In general terms, any solvent that contains a labile H⁺ is called a protic solvent. The molecules of such solvents readily donate protons (H⁺) to reagents. Conversely, aprotic solvents cannot donate hydrogen.

Video Protic solvent

Polar protic solvents

Polar protic solvents are often used to dissolve salts. In general, these solvents have high dielectric constants and high polarity.

Common characteristics of protic solvents :

• solvents display hydrogen bonding
• solvents have an acidic hydrogen (although they may be very weak acids such as ethanol)
• solvents dissolve salts
  • cations by unshared free electron pairs
  • anions by hydrogen bonding

Examples include water, most alcohols, formic acid, hydrogen fluoride, and ammonia. Polar protic solvents are favorable for S_N1 reactions, while polar aprotic solvents are favorable for S_N2 reactions.

Maps Protic solvent

Polar aprotic solvents

Polar aprotic solvents are solvents that lack an acidic hydrogen. Consequently, they are not hydrogen bond donors. These solvents generally have intermediate dielectric constants and polarity. Although discouraging use of the term "polar aprotic", IUPAC describes such solvents as having both high dielectric constants and high dipole moments, an example being acetonitrile. Other solvents meeting IUPAC's criteria include DMF, HMPA, and DMSO.

Common characteristics of aprotic solvents:

• solvents that can accept hydrogen bonds
• solvents do not have acidic hydrogen
• solvents dissolve salts

The criteria are relative and very qualitative. A range of acidities are recognized for aprotic solvents. Their ability to dissolve salts depends strongly on the nature of the salt.

Polar aprotic solvents are generally incompatible with strong bases, such as Grignard reagents or n-butyllithium. These reagents require ethers, not nitriles, amides, sulfoxides, etc.

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Properties of common solvents

The solvents are qualitatively grouped into non-polar, polar aprotic, and polar protic solvents, often ranked by dielectric constant.

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See also

• Autoprotolysis

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References

• Loudon, G. Mark. Organic Chemistry 4th ed. New York: Oxford University Press. 2002. pg 317.

Source of the article : Wikipedia