Oxidation of Some α-Hydroxy Acids by Tetraethylammonium Chlorochromate: A Kinetic and Mechanistic Study

被引：15

作者：

Swami, Preeti ^{[1
]}

Yajurvedi, D. ^{[1
]}

Mishra, P. ^{[1
]}

Sharma, Pradeep K. ^{[1
]}

机构：

[1] Jai Narain Vyas Univ, Dept Chem, Jodhpur 342005, Rajasthan, India

来源：

INTERNATIONAL JOURNAL OF CHEMICAL KINETICS | 2010年 / 42卷 / 01期

关键词：

QUINOLINIUM BROMOCHROMATE; PYRIDINIUM CHLOROCHROMATE; 2,2'-BIPYRIDINIUM CHLOROCHROMATE; SECONDARY ALCOHOLS; CARBONYL-COMPOUNDS; EFFICIENT REAGENT; CHROMIUM(VI); FLUOROCHROMATE; STOICHIOMETRY; OXIDANT;

D O I：

10.1002/kin.20466

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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 alpha-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. (C) 2009 Wiley Periodicals, Inc. Int J Chem Kinet 42: 50-55, 2010

引用

页码：50 / 55

页数：6

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