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A Novel Method to Quantify the Nucleophilicity of Dihydroxy Benzoic Acid Regioisomers by Polarography

Author Affiliations

  • 1Department of Chemistry, Nowrosjee Wadia College, affiliated to SPPU, Pune 411 001, India
  • 2Department of Chemistry, Nowrosjee Wadia College, affiliated to SPPU, Pune 411 001, India
  • 3Department of Chemistry, Nowrosjee Wadia College, affiliated to SPPU, Pune 411 001, India
  • 4Department of Chemistry, Nowrosjee Wadia College, affiliated to SPPU, Pune 411 001, India
  • 5Department of Chemistry, Nowrosjee Wadia College, affiliated to SPPU, Pune 411 001, India

Res.J.chem.sci., Volume 6, Issue (12), Pages 56-58, December,18 (2016)

Abstract

The reduction propensities of 2,6-dihydroxy benzoic acid (2,6-DBA) and 3,5-dihydroxy benzoic acid (3,5-DBA) in aqueous medium using classical polarography have been studied to portray their reactivity in aromatic substitution reactions in terms of their relative nucleophilicity. The half-wave reduction potentials for 2,6-DBA and 3,5-DBA have been found to be 800 and 900 mV respectively indicating lower nucleophilicity for 2,6-DBA than that of 3,5-DBA. These results have been confirmed from complementary data by kinetic studies for the iodination of these two regioisomers. This two-pronged complementary study assesses the reactivity of the two substrates in a quantitative manner.

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