Kinetics and Mechanism of the Mineral Acid Catalysed Reactions of Hydroxamic Acids

Abstract

Abstract There is currently a great deal of interest in the chemistry of hydroxamic acids. In recent years we have been studying the synthesis, structure and nucleophilicities of hydroxamic acids. This paper reports a kinetic study of reactivity of some hydroxamic acids RC(O)·N(OH)R′; R=C6H5·CH=CH, R′=4-CH3·C6H4 [p-tolylcinnamo hydroxamic acid]; R=C6H5, R′=4-CH3·C6H4 [p-tolylbenzo hydroxamic acid]; R=C6H5, R′=2-CH3·C6H4 [o-tolylbenzo hydroxamic acid] in aqueous mineral acids (HCl, HClO4 and H2SO4). The rate data of hydrolysis reaction revealed that the reactivity/stability sequence of the compounds is generally p-TBHA>o-TBHA>p-TCHA. An excess acidity analysis reveals that the reaction proceeds by nucleophilic attack of water molecule on the protonated substrate.