大学化学 >> 2025, Vol. 40 >> Issue (3): 68-75.doi: 10.12461/PKU.DXHX202404057

所属专题： 理论与计算化学在化学及其交叉学科教学中的应用

专题 上一篇    下一篇

量子化学计算方法研究溴丁烷E2消除反应——设计一个计算化学实验

穆雪丽1, 韩玲利1, 刘涛1,2   

  1. 1 济宁学院化学化工与材料学院, 山东 曲阜 273155;
    2 曲阜师范大学化学与化工学院, 山东 曲阜 273165
  • 收稿日期:2024-04-10 录用日期:2024-07-22 发布日期:2025-03-19
  • 通讯作者: 韩玲利, 刘涛 E-mail:hll_2002@sina.com;liutao_2005@126.com
  • 基金资助:
    山东省自然科学基金(ZR2022QB063)

Quantum Chemical Calculation Study on the E2 Elimination Reaction of Halohydrocarbon: Designing a Computational Chemistry Experiment

Xueli Mu1, Lingli Han1, Tao Liu1,2   

  1. 1 School of Chemistry, Chemical Engineering and Materials, Jining University, Qufu 273155, Shandong Province, China;
    2 School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong Province, China
  • Received:2024-04-10 Accepted:2024-07-22 Published:2025-03-19
  • Contact: Lingli Han, Tao Liu E-mail:hll_2002@sina.com;liutao_2005@126.com

PDF

483

赞

补充材料

1

摘要： 卤代烃E2消除反应是基础有机化学课程中的重要教学内容，由于缺乏直观形象化的描述导致学生理解困难。本文设计了一个面向化学本科专业的计算化学实验，通过量子化学计算阐明卤代烃发生E2消除反应的详细机理及其与SN2亲核取代反应的竞争机制，同时获取反应的热力学和动力学信息，帮助学生理解Zaitsev规则、选择性、反应热力学、反应动力学、过渡态、反应坐标等有机化学及物理化学中的基本概念。本实验旨在训练学生使用计算化学方法解决化学问题的基本思路，提升学生的科研素养。

关键词: 卤代烃, E2消除, Zaitsev规则, SN2亲核取代, 量子化学计算

Abstract: The E2 elimination reaction of halohydrocarbon is one of the most important reactions in foundational organic chemistry courses, however, the lack of visual description makes it difficult for undergraduates to understand the mechanism. This study designs a computational chemistry experiment for undergraduate chemistry majors, utilizing quantum chemical calculations to elucidate the detailed mechanism of E2 elimination and its competition mechanism with SN2 nucleophilic substitution. In this experiment, we obtained thermodynamic and kinetic properties of E2 elimination reaction, helping students understand fundamental concepts such as Zaitsev’s rule, selectivity, reaction thermodynamics, reaction kinetics, transition states, and reaction coordinates, which are integral to both organic and physical chemistry. The primary goal of this experiment is to train students in using computational chemistry methods to solve chemical problems, thereby enhancing their scientific research skills and scientific research literacy.

Key words: Halohydrocarbon, E2 elimination reaction, Zaitsev’s rule, SN2 nucleophilic substitution, Quantum chemical calculation