Two-phase azo-coupling reactions driven by phase-boundary potential across the liquid|liquid interface

Young Tae Kong, Shinichiro Imabayashi, Takashi Kakiuchi

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Phase-boundary-potential-driven azo coupling has been demonstrated for the reaction between hydrophilic arenediazonium ions and lipophilic Coupling components in 1,2-dichlroethane (DCE)|water (W) two-phase systems. Instead of using phase-transfer catalysts, hydrophilic arenediazonium ions are driven into the DCE phase by externally controlling the potential drop across the polarized DCE|W interface. The diffusion-controlled transfer of arenediazonium ions across the interface is followed by az-coupling reactions with coupling components in the DCE phase. The rate of the azo coupling in DCE has been accurately determined by using potential-step chronoamperometry for the transfer for four arenediazonium ions having different lipophilicity in the presence of one of four aromatic coupling components in DCE. No appreciable contribution of the adsorbed reactants to the overall azo-coupling process is detected. An electrochemical approach using liquid|liquid two-phase systems is advantageous in determining the rate of two-phase chemical reactions and is promising for elucidating the mechanism of phase-transfer catalysis.

Original languageEnglish
Pages (from-to)8215-8219
Number of pages5
JournalJournal of the American Chemical Society
Volume122
Issue number34
DOIs
Publication statusPublished - 2000 Aug 30
Externally publishedYes

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Phase boundaries
Ions
Liquids
Chronoamperometry
Catalysis
Chemical reactions
Catalysts
Water

ASJC Scopus subject areas

  • Chemistry(all)

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Two-phase azo-coupling reactions driven by phase-boundary potential across the liquid|liquid interface. / Kong, Young Tae; Imabayashi, Shinichiro; Kakiuchi, Takashi.

In: Journal of the American Chemical Society, Vol. 122, No. 34, 30.08.2000, p. 8215-8219.

Research output: Contribution to journalArticle

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