Abstract
In order to study the structure-reactivity relationship in the intramolecular catalyzed hydrolysis of amide, a series of aliphatic hydroxyamides was subjected to acid-catalyzed hydrolysis. Paper chromatogram verified that the hydroxyamides, which had high rates compared with those of the corresponding alkyl analogues, produced the corresponding lactones in their hydrolytic processes. Their reaction pathways were classified theoretically into three schema. The Arrhenius parameters of entropy and enthalpy or activation were determined and the mechanisms of lactonization and hydroxy acid formation were discussed from entropy-enthalpy relationship. The proposed mechanisms were supported by the appropriate kinetic data.
