Solvolysis of 2-Thiophenesulfonyl Chloride

2-염화티오펜술포닐의 가용매 분해반응

  • Jin-Chel Choi (Department of Science Education, Gyeongsang National University) ;
  • Jieun Oh (Department of Science Education, Gyeongsang National University) ;
  • Dae Ho Kang (Department of Science Education, Gyeongsang National University) ;
  • In Sun Koo (Department of Science Education, Gyeongsang National University) ;
  • Ikchoon Lee (Department of Chemistry, Inha University)
  • 최진철 (경상대학교 사범대학 과학교육과) ;
  • 오지은 (경상대학교 사범대학 과학교육과) ;
  • 강대호 (경상대학교 사범대학 과학교육과) ;
  • 구인선 (경상대학교 사범대학 과학교육과) ;
  • 이익춘 (인하대학교 이과대학 화학과)
  • Published : 1993.08.20

Abstract

Rate constants of solvolysis of 2-thiophenesulfonyl chloride were determined in aqueous binary mixtures with methanol, ethanol, acetone in water and in methanol. These data are interpreted using the equation of Grunwald-Winstein and Kivinen relationship. Also, kinetic solvent isotope effects in water and in methanol and product selectivities in alcohol-water mixtures were determined. Kinetic solvent isotope effect for hydrolysis of 2-thiopenesulfonyl chloride was 2.24 and 1.47 for methanol and water, respectively. Selectivity values for formation of ester relative to acid in ethanol-water mixtures show maximum S value. From kinetic solvent isotope effect in methanol and water, selectivity data in aqueous alcoholic solvents and solvent effects, it is proposed that the reaction channel favoured in low polarity solvents is general-base catalysis and/or is possibly addition elimination (S$_A$N) reaction pathway and in high polarity solvents iS S$_N$2 reaction mechanism.

Keywords

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