大学化学 >> 2022, Vol. 37 >> Issue (7): 2110088.doi: 10.3866/PKU.DXHX202110088

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硫-氟的邻位交叉效应

李懿伦, 余意, 袁耀锋(), 叶克印()   

  • 收稿日期:2021-10-28 录用日期:2021-11-29 发布日期:2021-12-24
  • 通讯作者: 袁耀锋,叶克印 E-mail:yaofeng_yuan@fzu.edu.cn;kyye@fzu.edu.cn
  • 作者简介:Email: kyye@fzu.edu.cn (叶克印)
    Email: yaofeng_yuan@fzu.edu.cn (袁耀锋)
  • 基金资助:
    福州大学一流学科本科教学改革建设项目;中国高等教育学会2021年度理科专项课题(21LKYB07)

The Sulfur-Fluorine Gauche Effect

Yilun Li, Yi Yu, Yaofeng Yuan(), Keyin Ye()   

  • Received:2021-10-28 Accepted:2021-11-29 Published:2021-12-24
  • Contact: Yaofeng Yuan,Keyin Ye E-mail:yaofeng_yuan@fzu.edu.cn;kyye@fzu.edu.cn

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摘要：

乙烷分子中相邻的两个氢原子被氟取代以后，它的最优构象就从全交叉式转变为邻位交叉，这就是邻位交叉效应影响分子构象最具代表性的一个例子。本文简要回顾了含氟邻位交叉效应的发展历史与重要应用，重点介绍了物理有机科研前沿的硫-氟邻位交叉效应。结合当前最新的科研成果，验证了通过改变硫原子的电正性可以达到有效调控邻位交叉效应这一重要策略。通过科研反哺教学，有助于进一步加深对硫-氟邻位交叉效应的理解和认识。

关键词: 邻位交叉效应, 立体电子效应, 构象

Abstract:

The most favored anti-conformation of ethane would turn into gauche-conformation when the vicinal hydrogen atoms are replaced by two fluorine atoms. Such a switch shows how the gauche effect impacts the relative conformation of organic molecules. Herein, we briefly survey the history of the gauche effect as well as its broad applications in organic synthesis. Particularly, we highlight the recent investigations on the related sulfur-fluorine gauche effect. With the aid of experiments, we confirmed that the sulfur-fluorine gauche effect could be easily regulated via the subtle change of positive charges on the sulfur atom. Such a positive interplay between scientific research and organic course teaching would profoundly help students to understand the basic concepts and advanced applications of the sulfur-fluorine gauche effect.

Key words: Gauche effect, Stereoelectronic effect, Conformation