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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/113/01/0043-0054

    • Keywords

       

      Diols; benzyltrimethylammonium tribromide; oxidation; kinetics; mechanism; kinetic isotope effect

    • Abstract

       

      The kinetics of oxidation of five vicinal and four non-vicinal diols, and two of their monoethers by benzyltrimethylammonium tribromide (BTMAB) have been studied in 3:7 (v/v) acetic acid-water mixture. The vicinal diols yield the carbonyl compounds arising out of the glycol bond fission while the other diols give the hydroxycarbonyl compounds. The reaction is first-order with respect to BTMAB. Michaelis-Menten type kinetics is observed with respect to diol. Addition of benzyltrimethylammonium chloride does not affect the rate. Tribromide ion is postulated to be the reactive oxidizing species. Oxidation of [1,1,2,2-2H4] ethanediol shows the absence of a kinetic isotope effect. The reaction exhibits substantial solvent isotope effect. A mechanism involving a glycol-bond fission has been proposed for the oxidation of the vicinal diols. The other diols are oxidized by a hydride ion transfer to the oxidant, as are the monohydric alcohols.

    • Author Affiliations

       

      Garima Goswami1 Seema Kothari1 Kalyan K Banerji1

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

       
  • Journal of Chemical Sciences | News

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