1. Home
    2. Journals
    3. Journal of Chemical Sciences
    4. Volume 100
    5. Issue 5

    • Separation of polar and steric effects in the oxidation of ortho-substituted benzaldehydes by N-bromobenzamide

      Kalyan K Banerji

      Organic Volume 100 Issue 5 October 1988 pp 397-403

    • Fulltext

       

        Click here to view fulltext PDF


      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/100/05/0397-0403

    • Keywords

       

      Ortho-effect; correlation analysis; benzaldehydes; N-bromobenzamide; oxidation

    • Abstract

       

      The kinetics of the oxidation of twelve ortho-substituted benzaldehydes by N-bromobenzamide (NBB) to the corresponding benzoic acids have been studied. The reaction is first order with respect to NBB, the aldehyde and hydrogen ions. The addition of benzamide has no effect on the reaction rate. (PhCONH2Br)+ has been postulated as the reactive oxidising species. The correlation of rates with the single substituent-parameter equations is poor. The correlation with Charton’s equation of inductive, resonance and steric parameters is satisfactory. However, excellent correlations were obtained, when Charton’s steric parameter was used along with Taft’s σ1; andσR+ substituent constants. The polar reaction constants have negative values. The reaction is subject to steric hindrance by the ortho-substituents.

    • Author Affiliations

       

      Kalyan K Banerji1

      1. Department of Chemistry, University of Jodhpur, Jodhpur - 342 001, India

    • Dates

       
      Published
      October 1988
      Manuscript received
      28 December 1987
      Manuscript revised
      25 March 1988

  • Journal of Chemical Sciences | News

© 2023-2024 Indian Academy of Sciences, Bengaluru.

Contact | Site index