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|Title:||Kinetics and mechanism of the oxidation of some α-hydroxy acids by benzyltriethylammonium chlorochromate|
Sharma, Pradeep K
|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.|
|Appears in Collections:|| IJC-A Vol.45A(10) [October 2006]|
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