大学化学 >> 2022, Vol. 37 >> Issue (12): 2112089.doi: 10.3866/PKU.DXHX202112089

师生笔谈 上一篇    下一篇

量子化学计算揭示开链共轭烯烃电环化反应的立体选择规则

马雪香, 刘成卜, 张冬菊()   

  • 收稿日期:2021-12-30 录用日期:2022-02-08 发布日期:2022-03-14
  • 通讯作者: 张冬菊 E-mail:zhangdj@sdu.edu.cn
  • 作者简介:张冬菊, Email: zhangdj@sdu.edu.cn
  • 基金资助:
    国家自然科学基金(21773139)

Revealing the Stereoselective Rule of Electrocyclic Reactions of Chain Conjugated Polyenes by Performing Quantum Chemical Calculations

Xuexiang Ma, Chengbu Liu, Dongju Zhang()   

  • Received:2021-12-30 Accepted:2022-02-08 Published:2022-03-14
  • Contact: Dongju Zhang E-mail:zhangdj@sdu.edu.cn

摘要:

开链共轭多烯的电环化反应是本科基础化学课程中的重要教学内容,本文以最简单的4n和4n+2型开链共轭烯烃为例,设计了一个基于量子化学计算的教学案例,定量、直观描述电环化反应的立体选择性,旨在使学生加深对电环化反应规律的认识,强化对前线轨道理论、分子轨道对称守恒原理等基本理论的理解。

关键词: 链状共轭烯烃, 电环化反应, 立体选择性, 密度泛函理论计算

Abstract:

The electrocyclization reaction of chain conjugated polyenes is an important teaching content in the basic chemistry course of undergraduates. Taking the simplest 4n and (4n+2) chain conjugated polyenes as examples, this paper designs a teaching case based on quantum chemical calculations to quantitatively and intuitively describe the stereoselectivity of electrocyclization reactions of chain conjugated polyenes, in order to enable students to deepen their understanding of the electrocyclization reaction mechanism, frontier orbital theory, and molecular orbital symmetry conservation principle.

Key words: Chain conjugated polyenes, Electrocyclic reactions, Stereoselectivity, DFT calculations

MSC2000: 

  • G64