Kinetic and Mechanistic Profile of Some Phenolic Compounds by N-Chlorosaccharin in Aqueous Acid Medium

Author: Sangeeta Sinha, S.P. Singh and M.N. Swami

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Abstract

We report the mechanistic approach of oxidation of some phenolic compounds such as catechol and cresol by N-chlorosaccharin in different compositions of acetic acid-water medium. The reaction is first-order with respect to oxidant and order varies from one to zero with respect to both [phenolic compounds] and [acid]. A positive effect of solvent establishes a positive ion-dipole interaction whereas added saccharin exhibits a negative effect on rate. Kinetic profile for consumption of fivefold of [NCSA] was obtained at reaction conditions which followed first-order kinetics, substantiated by unit slope evaluated from the parallel plot of log10 (a-x) versus time plot. The stoichiometry of the oxidation is 2:1 demonstrating the formation of transitory complex between substrate and the protonated species of NCSA, which are readily oxidized to products. A plausible mechanism supported by substituent, abstraction of proton by Lewis base and temperature effect has been proposed.

Keywords

Catechol, Þ-cresol, N-chlorosaccharin, Kinetics, Oxidation