Structure–reactivity relationships in the rate of esterification by acetylimidazole: the influence of the second hydroxy group and of the length of the N-ω-hydroxy-n-alkyl chain in 3-(N-methyl, N-ω-hydroxy-n-alkyl)amino-2- tert-butylpropan-1-ols

Abstract

Enforced intramolecular hydrogen bonding facilitates intramolecular general base catalysis in the acetylation of a family of α,ω-amino alcohols by acetylimidazole, and the site of acetylation when there are two hydroxy groups is determined by the relative ease of intramolecular hydrogen bonding rather than by intermolecular steric effects.