The α-deuterium secondary kinetic isotope effect upon the hydrolysis of 2-(p-nitrophenoxy)tetrahydropyran and its relationship to values for the solvolysis of secondary alkyl arenesulfonates and the enzyme-catalysed hydrolysis of acetals

Abstract

The α-deuterium secondary kinetic isotope effect for the uncatalysed hydrolysis of 2-(p-nitrophenoxy)tetrahydropyran is 1.17 in water (46°C), a result which is very similar to values for the solvolysis of simple secondary alkyl arenesulfonates which proceed with rate-limiting ionization and appreciably higher than results for enzyme-catalysed hydrolysis of other acetals.