Kinetic Study on Nucleophilic Substitution of 1-Anthracenesulfonyl Chloride with Anilines

1-염화안트라센 술포닐의 치환아닐린과의 친핵성치환반응의 속도론적 연구

  • Kim Hyong Tae (Department of the Chemical Education, Busan National University) ;
  • Yoh Soo Dong (Department of Chemical Education, Kyungpook National University)
  • 김형태 (부산대학교 사범대학 화학교육과) ;
  • 여수동 (경북대학교 사범대학 화학교육과)
  • Published : 1985.04.20

Abstract

1-Anthracenesulfonyl chloride used as a substrate has been prepared from anthra-quinone, and its melting point ($124^{circ}C$) was confirmed to be considerably different from the literature value ($90^{circ}C$). Rates of nucleophilic substitution reactions of this substrate with some p-substituted anilines in dry acetone were determined by electroconductometric method, and their mechanism has been discussed. As a result, it has been found that these reactions proceed in parallel catalyzed by anilines together with noncatalyzed process, and that their catalytic activities are electrophilic. Judging from $Br{\phi}nsted\;{\beta}$ (0.77), Hammett ${\rho}$(-3.2), and activation parameters which were determined from the temperature dependence of noncatalyzed second order rate constants, it appears most appropriate that their mechanism should be discussed in terms of an associative $S_N2$ involving sulfonylammonium intermediate.

Keywords

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