Nucleophilic Displacement at Sulfur Center (Ⅸ). Solvolysis of Naphthalene Sulfonyl Chlorides in Acetone Water Mixtures

황의 친핵성 치환반응 (제9보). 물-아세톤 혼합용매 속에서 1-염화 및 2-염화나프탈렌 술포닐의 가용매 분해반응

  • Uhm Tae Seop (Department of Chemistry, Dong A University) ;
  • Lee Ik Choon (Department of Chemistry, In Ha University) ;
  • Lee Euk Suk (Department of Chemistry, Busan National University)
  • 엄태섭 (동아대학교 문리과대학 화학과) ;
  • 이익춘 (인하대학교 이과대학 화학과) ;
  • 이억석 (부산대학교 문리과대학 화학과)
  • Published : 1977.08.30

Abstract

The solvolysis of 1-naphthalene-and 2-naphthalenesulfonyl chlorides in acetone-water mixtures have been studied by means of conductometry. The solvent effect and mechanism have been discussed in terms of variation in solvent composition and activation parameters. The reaction was predominantly $S_N2$ type, but bond breaking increased with the increase of water content. The rate constant for 1-naphthyl compound was smaller than that of 2-naphthyl compound due to the ground state stabilization effect and peri-hydrogen effect, and the latter effect was similar to that in ethanol-water mixtures.

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References

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