Intramolecular catalysis. Part 2. Mechanism of hydrolysis of alkyl 8-hydroxy-1-naphthoates

Abstract

The hydrolysis of alkyl 8-hydroxy-1 -naphthoates in alkaline 30%(v/v) dioxan–water has been investigated. The pH′-rate profiles, activation parameters, comparison with the rates of hydrolysis of model compounds and 8-hydroxy1 -naphthoic acid lactone, and kinetic solvent isotope and other effects indicate a mechanism involving intramolecular catalysis, either by general base or by general acid specific base. The significance of the results is discussed in relation to the factors governing such mechanistic pathways.