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Protons: Affinity and Reduction in Ionic Liquids

Proton affinities dictate that protic salts are dissociated into molecules in the gas phase. In the liquid phase, protons are associated with charge neutral base molecules or homoconjugate/heteroconjugate anions. For example, liquids prepared from a base and a hydrogen halide contain the protonated base and either the halide or the halohydrogenate(I) anion; thus 2 classes of proton may be available for reduction. It happens that the anionic protic species are more readily reduced. This situation extends to complex hydrogen halides and anhydrous carboxylic acids. NMR data provide evidence of proton transfer and spectrophotometry can give a measure of acidity. Protic species alone may or may not ionize, depending on the proton affinity of the species itself. The formation of salts from a base and a protic species is discussed in terms of the pair of dissociation constants for dimethylsulphoxide, acetonitrile, water, and the gas phase, with limitations imposed by solvent leveling noted.