Hydrolysis of amides. V. Alkaline hydrolysis of alkyl-substituted amides

Abstract

Enthalpies and entropies of activation have been derived from rate constants measured over a range of temperature for the alkaline hydrolysis of acetamide, propionamide, n-butyramide, n-valeramide, isovaleramide, phenylacetamide, cyclohexylacetamide, methoxyacetamide, cyclohexanecarboxamide, cyclopentane carboxamide, α-methylbutyramide, isobutyramide, and trimethylacetamide. ��� These results are discussed in terms of their correlation by Taft- type equations which have been extended to incorporate a factor based upon the ?α-hydrogen bond? concept of hyperconjugative stabilization. The rate constants of these 13 amides under these conditions appear to be governed by a combination of polar, steric, and hyperconjugative factors.