• Alkaline hydrolysis of arylesters of diphenylphosphorodiamidates—evidence consistent with an elimination—addition mechanism

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    • Keywords


      Diphenylphosphorodiamidate esters; alkaline hydrolysis; E1CB mechanism

    • Abstract


      The alkaline hydrolysis of a series of aryl phosphorodiamidates has been studied in aqueous ethanol and aqueous DMSO mixtures. Although the reactions do not show any saturation kinetics with respect to the hydroxide ion, the low solvent isotope effect, the highly negative Bronsted β value, the large Hammett ρ for the leaving aryloxy group and the decrease in rate with increase in the proportion of DMSO in the solvent mixtures indicate that the hydrolysis proceeds by an elimination-addition pathway. Comparison of rate data with other hydrolytic E1CB reactions show that the title reaction belongs to the (E1CB)R category.

    • Author Affiliations


      P Krishnan1 S Sundaram1 N Venkatasubramanian1 2

      1. Department of Chemistry, R K M Vivekananda College, Madras - 600 004, India
      2. IDL Nitro Nobel Basic Research Institute, Bangalore - 560 003, India
    • Dates

  • Journal of Chemical Sciences | News

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