Journal of Physical Organic Chemistry p. 105 - 110 (1996)
Update date:2022-08-17
Topics:
Karunakaran
Elango
The oxidation of several monosubstituted phenoxyacetic acids by pyridinium hydrobromide perbromide (PHPB) was studied in aqueous acetic acid. The reaction is first order with respect to PHPB. Michaelis-Menten-type kinetics are observed with respect to phenoxyacetic acids. The oxidation of [2,2-2H2]phenoxyacetic acid exhibits a substantial kinetic isotopic effect. The effect of solvent composition indicates that the transition state is more polar than the reactants. The formation constants of the intermediate phenoxyacetic acid-PHPB complexes and the rates of their decomposition were determined at different temperatures. The rates of oxidation of para- and meta-substituted phenoxyacetic acids were correlated with Hammett's substituent constants. The ρ value is -2.59 at 35 °C. The rates of oxidation of ortho-substituted compounds are correlated with Charton's triparametric equation. A mechanism involving transfer of a hydride ion from the substrate to the oxidant is proposed.
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