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Mechanistic investigations of the oxidation of phenethyl alcohols by sodium-N-bromo-benzenesulphonamide in acid medium

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Abstract

The kinetics of oxidation of six substituted phenethyl alcohols (X-C6H4-CH2-CH2-OH where X=-H, -Cl, -Br, -CH3, -OCH3 and -NO2) by sodium-N-bromo-benzenesulphonamide or bromamine-B(BAB) in the presence of HCl at 35°C showed that the rate has first-order dependence on [BAB]0 and [H+] and fractional order on [PEA]0 and [Cl−]. Ionic strength variations, addition of reaction product of benzenesulphonamide and variation of dielectric constant of the medium have no effect on the rate. The solvent isotope effectk 1(H2O)/k 1(D2O)⊇0.82. Proton inventory studies have been made in H2O-D2O mixtures. The Hammett plot is biphasic and the reaction constantρ was −3.2 for electron-releasing substituents and −0.34 for electron-withdrawing groups. The activation parameters ΔH #, ΔS # follow an isokinetic relationship.

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Authors and Affiliations

  1. Department of Studies in Chemistry, University of Mysore, 570 006, Manasagangotri, Mysore, India

    D S Mahadevappa & K S Rangappa

  2. Department of Chemistry, P E S College of Engineering, 571 401, Mandya, India

    H Ramachandra

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  1. H Ramachandra
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  2. D S Mahadevappa
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  3. K S Rangappa
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Ramachandra, H., Mahadevappa, D.S. & Rangappa, K.S. Mechanistic investigations of the oxidation of phenethyl alcohols by sodium-N-bromo-benzenesulphonamide in acid medium. Proc. Indian Acad. Sci. (Chem. Sci.) 108, 485–494 (1996). https://doi.org/10.1007/BF02869553

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  • DOI: https://doi.org/10.1007/BF02869553

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