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Title: Kinetics and mechanism of the oxidation of some α-hydroxy acids by benzyltriethylammonium chlorochromate
Authors: Pohani, Poonam
Sharma, Pradeep K
Issue Date: Oct-2006
Publisher: NISCAIR-CSIR, India
IPC Code: Int. Cl.8 C07B33/00
Abstract: The oxidation of glycolic, lactic, malic and  a few substituted mandelic acids by benzyltriethylammonium chlorochromate (BTEACC) in dimethyl sulphoxide  leads to formation of the corresponding oxoacids. The reaction is first order in BTEACC. Michaelis- Menten type of kinetics is observed with respect to the hydroxy acids. Polymerisation of acrylonitrile is not induced in this reaction. The oxidation of α-deuteriomandelic acid shows primary kinetic isotope effect (k11/kD) = 5.51at 298 K). The reaction does not exhibit the solvent isotope effect. The reaction is catalysed by hydrogen ions and hydrogen ion dependence has the form: kobs = a+b [H+].  Oxidation of p-methyl mandelic acid has been studied in 19 different organic solvents. The solvent effect has been analysed by using Kamlet's and Swain's multiparametric equations. A mechanism involving a hydride ion transfer  via a chromate ester is proposed.
Page(s): 2218-2223
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections: IJC-A Vol.45A(10) [October 2006]

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