• Kinetics and mechanism of the oxidation ofα-hydroxy acids by benzyltrimethylammonium chlorobromate

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      https://www.ias.ac.in/article/fulltext/jcsc/111/06/0741-0746

    • Keywords

       

      α-Hydroxy acids; benzyltrimethylammonium chlorobromate; kinetic isotope effect; hydride ion transfer

    • Abstract

       

      The oxidation of glycollic, lactic, malic and a few substituted mandelic acids by benzyltrimethylammonium chlorobromate (BTMACB) in acetic acid-water (1:1) leads to the formation of the corresponding oxoacids. The reaction is of first order in BTMACB as well as the hydroxy acid. Addition of benzyltrimethylammonium chloride or bromide ion does not affect the rate indicating that BTMACB itself is the reactive oxidizing species. The oxidation ofα-deuteriomandelic acid shows the presence of a primary kinetic isotope effect (kH/kD=5·27 at 303 K). The reaction does not exhibit the solvent isotope effect [k(H2O)/k(D2O)=1·01]. The rate decreases with increase in the amount of acetic acid in the solvent mixture. A mechanism is proposed which involves hydride ion transfer to the oxidant.

    • Author Affiliations

       

      Anjana1 Pradeep K Sharma1 Kalyan K Banerji1

      1. Department of Chemistry, JNV University, Jodhpur - 342 005, India
    • Dates

       
  • Journal of Chemical Sciences | News

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