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Acids and BasesSolvent Effects on Acid-Base Strength$
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Brian G. Cox

Print publication date: 2013

Print ISBN-13: 9780199670512

Published to Oxford Scholarship Online: May 2013

DOI: 10.1093/acprof:oso/9780199670512.001.0001

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Solvation and Acid–Base Strength

Solvation and Acid–Base Strength

(p.21) 3 Solvation and Acid–Base Strength
Acids and Bases

Brian G. Cox

Oxford University Press

The change in dissociation constant of an acid with solvent is directly and quantitatively related to the change in solvation energies of the species involved. The solvation of electrolytes and non-electrolytes across a wide range of solvents is reviewed. The transfer of simple anions from water to non-aqueous solvents is almost universally unfavourable because of the loss of important hydrogen-bond interactions with water. Cation solvation is strongly dependent upon the basicity of the solvent. It is highly favourable in solvents such as dimethylsulphoxide, which are strong Lewis bases, but much weaker than water in low-polarity and low-basicity solvents such as acetonitrile and tetrahydrofuran. Non-electrolytes, such as carboxylic acids and amines, are more stable in non-aqueous media, but the effects are generally much smaller than for ions. In mixed solvents, preferential solvation by the most favourable solvent component determines the dependence of solvation and dissociation constants upon solvent composition.

Keywords:   solvation free-energies, solubility, vapour pressure, distribution coefficients, mixed solvents, preferential solvation

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