Abstract
New σ * values of some α-mercapto and α-alkoxy groups have been obtained from the kinetic measurements of acidic and alkaline hydrolyses of ethyl α-substituted carboxylates. The acid dissociation constants and UV spectra of these carboxylic acids are discussed using these newly obtained σ * values. The relative dissociation constants of α-substituted carboxylic acids cannot be accounted for by the polar effects only since the steric inhibition of solvation around the carboxylate ion by α-substituents plays an important role. In addition, the non-bonding interaction between the α-mercapto group and the carboxylate ion appears to be significant.
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