Electrochemical Study of the SN2 Reaction of 1-p-Toluenesulfonyl-2,4-dinitronaphthalene with Hydroxide Ions at the Nitrobenzene-Water Interface

Young Tae Kong, Shin Ichiro Imabayashi, Takashi Kakiuchi

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8 Citations (Scopus)

Abstract

The rate of the interfacial nucleophilic reaction of 1-p-toluenesulfonyl-2,4-dinitronaphthalene (TSDNN) with OH- ions at the polarized nitrobenzene (NB)-water (W) interface was studied using a polarographic technique. The TSDNN partitioned into the aqueous phase underwent a displacement of the p-toluenesulfonyl moiety with OH-. The transfer of one of the products, 2,4-dinitronaphthalate (DNN-), from the W phase to the NB phase was monitored as the current across the interface. The rate constant of the reaction of TSDNN with OH- in the aqueous phase was estimated to be 1.03±0.23 dm3 mol-1 s-1 at 25°C, which is ten-times higher than the rate constant of the displacement of 2,4-dinitrofluorobenzene with OH- in the aqueous phase, 1.01±0.13×10-1 dm3mol-1 s-1. The contribution from the reactions in the NB phase and at the interface to the formation of DNN- seems to be negligible, suggesting the absence of an interfacial facilitation of the reaction.

Original languageEnglish
Pages (from-to)121-125
Number of pages5
JournalAnalytical Sciences
Volume14
Issue number1
DOIs
Publication statusPublished - 1998
Externally publishedYes

Keywords

  • 1-p-toluenesulfonyl-2,4-dinitronaphthalene
  • Nucleophilic substitution reaction
  • Polarized nitrobenzene-water interface
  • Polarography
  • S2 reaction

ASJC Scopus subject areas

  • Analytical Chemistry

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