Concurrent oxygen-18 exchange accompanying the acid-catalyzed hydrolysis of anilides. Implications for the lifetimes of reversibly formed intermediates

AJ Bennet, H Slebocka-Tilk, RS Brown…

Index: Bennet; Slebocka-Tilk; Brown; Guthrie, J. Peter; Jodhan Journal of the American Chemical Society, 1990 , vol. 112, # 23 p. 8497 - 8506

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Citation Number: 39

Abstract

Abstract: Hydrolysis of acetanilide and N, 2, 4-trimethylacetanilide in acid is accompanied by oxygen exchange. The log k,, and log k,, vs-log [H+] profiles are parallel and show no significant divergence. The deuterium solvent kinetic isotope effects on exchange and hydrolysis are unity. A possible alternative mechanism for exchange in acetanilides involving enolization and elimination to give a transient keteniminium ion has been ruled ...