The influence of anchoring substitution in 1,3-amino alcohols on the rate and mechanism of esterification by acetylimidazole and by p-nitrophenyl acetate

Abstract

Enforced intramolecular hydrogen bonding in 2-tert-butyl-3-(NN-dimethylamino)propan-1-ol is shown by the competitive alcoholysis of p-nitrophenyl acetate and 1-acetylimidazole in acetonitrile, and by the corresponding second-order rate constants and activation parameters, to influence both the rate and the mechanism of catalysed acyl transfer.