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    • Dimple Garg

      Articles written in Journal of Chemical Sciences

    • Volume 116 Issue 6 November 2004 pp 333-338 Full Papers

      Kinetics and mechanism of the oxidation of some α-hydroxy acids by hexamethylenetetramine-bromine

      Dimple Garg Seema Kothari

      More Details Abstract Fulltext PDF

      The oxidation of lactic acid, mandelic acid and ten monosubstituted mandelic acids by hexamethylenetetramine-bromine (HABR) in glacial acetic acid, leads to the formation of the corresponding oxoacid. The reaction is first order with respect to each of the hydroxy acids and HABR. It is proposed that HABR itself is the reactive oxidizing species. The oxidation of α-deuteriomandelic acid exhibits the presence of a substantial kinetic isotope effect (kH/kD = 5.91 at 298 K). The rates of oxidation of the substituted mandelic acids show excellent correlation with Brown’s σ+ values. The reaction constants are negative. The oxidation exhibits an extensive cross conjugation between the electron-donating substituent and the reaction centre in the transition state. A mechanism involving transfer of a hydride ion from the acid to the oxidant is postulated.

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