Mechanism of Oxidation of p-Substituted Phenylthioacetic Acids with N-ChlorosaccharinReport as inadecuate

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E-Journal of Chemistry - Volume 8 2011, Issue 1, Pages 159-166

P.G and Research Department of Chemistry, Khadir Mohideen College, Adirampattinam-614 701, India

Received 28 June 2010; Accepted 18 August 2010

Copyright © 2011 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


The kinetics of oxidation of phenylthioacetic acid PTAA with N-chlorosaccharin NCSA have been studied potentiometrically in 80:20 v-v acetonitrile-water medium at 298 K. The reaction is first-order each with respect to PTAA and NCSA and shows a negative dependence on H

. NCSA itself is shown to be the active oxidizing species. Effects of ionic strength variation, added saccharin, added acrylonitrile, added NaCl and solvent composition variation have been studied. Effect of substituents on the reaction rate has been analysed by employing various p-sustituted phenylthioacetic acids. The electron-releasing substituent in the phenyl ring of PTAA accelerates the reaction rate while the electron-withdrawing substituent retards the rate. The excellently linear Hammett plot yields a large negative ρ value, supporting the involvement a chlorosulphonium ion intermediate in the rate-determining step.

Author: N. M. I. Alhaj, A. M. Uduman Mohideen, and S. Sofia Lawrence Mary



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