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Oxidation of some α-hydroxy acids by tetraethylammonium chlorochromate: A kinetic and mechanistic study

✍ Scribed by Preeti Swami; D. Yajurvedi; P. Mishra; Pradeep K. Sharma

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
96 KB
Volume
42
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The oxidation of glycolic, lactic, malic, and a few substituted mandelic acids by tetraethylammonium chlorochromate (TEACC) in dimethylsulfoxide leads to the formation of corresponding oxoacids. The reaction is first order each in TEACC and hydroxy acids. Reaction is failed to induce the polymerization of acrylonitrile. The oxidation of α‐deuteriomandelic acid shows the presence of a primary kinetic isotope effect (k~H~/k~D~ = 5.63 at 298 K). The reaction does not exhibit the solvent isotope effect. The reaction is catalyzed by the hydrogen ions. The hydrogen ion dependence has the following form: k~obs~ = a + b[H^+^]. Oxidation of p‐methylmandelic acid has been studied in 19 different organic solvents. The solvent effect has been analyzed by using Kamlet's and Swain's multiparametric equations. A mechanism involving a hydride ion transfer via a chromate ester is proposed. © 2009 Wiley Periodicals, Inc. Int J Chem Kinet 42: 50–55, 2010

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