大学化学 >> 2025, Vol. 40 >> Issue (3): 206-214.doi: 10.12461/PKU.DXHX202407022

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

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计算化学实验助力有机反应机理学习——以HCl与不对称烯烃的亲电加成反应为例

王渭娜1, 冯丽霞2, 刘峰毅1, 王文亮1,3   

  1. 1 陕西师范大学化学化工学院, 西安 710119;
    2 太原师范学院化学与材料学院, 山西 晋中 030619;
    3 安徽师范大学化学与材料科学学院, 安徽 芜湖 241000
  • 收稿日期:2024-07-01 录用日期:2024-10-16 发布日期:2025-03-19
  • 通讯作者: 王文亮 E-mail:wlwang@snnu.edu.cn
  • 基金资助:
    2022年陕西师范大学“课程思政”示范课建设项目(物理化学实验)；陕西省一流课程(结构化学)；安徽省课程思政(结构化学)

Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes

Weina Wang1, Lixia Feng2, Fengyi Liu1, Wenliang Wang1,3   

  1. 1 School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China;
    2 College of Chemistry and Materials, Taiyuan Normal University, Jinzhong 030619, Shanxi Province, China;
    3 School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, Anhui Province, China
  • Received:2024-07-01 Accepted:2024-10-16 Published:2025-03-19
  • Contact: Wenliang Wang E-mail:wlwang@snnu.edu.cn

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摘要： 将计算化学实验与有机化学课程相结合，既可提升学生软件应用能力和科研创新思维与能力，培养学生通过计算化学手段高效解决化学研究问题的能力，又可加深对反应机理的理解。本文以不对称烯烃CH2 = CHR (R = CH3，Cl，CN)与HCl亲电加成反应为例，通过构建反应路径，获得反应热力学和动力学数据，分析反应路径上驻点自然布居分析(NPA)电荷的变化，探讨取代基对反应机理影响的本质。本计算化学实验旨在加深学生对不对称烯烃亲电加成反应机理的认识和理解，并掌握计算化学研究化学反应机理的基本方法。

关键词: 计算化学实验, 不对称烯烃, 亲电加成反应, 密度泛函理论

Abstract: The combination of computational chemistry experiments with organic chemistry courses can not only enhance students' software application capabilities and scientific research innovation thinking and abilities, but also cultivate their ability to efficiently solve chemical research problems through computational chemistry and deepen their understanding of reaction mechanisms. In this paper, the electrophilic addition of HCl to asymmetric alkenes CH2 = CHR (R = CH3, Cl, CN) is taken as an example, the Markovnikov and anti-Markovnikov addition reaction paths are constructed to obtain the thermodynamic and kinetic data. The changes in NPA charge at the stationary points along the reaction path are analyzed to explore the essence of the influence of substituents on reaction mechanism. This computational chemistry experiment is designed to deepen students’ understanding and cognition of the electrophilic addition mechanism of asymmetric alkenes, and to grasp the fundamental methods of using computational chemistry to study chemical reaction mechanisms.

Key words: Computational chemistry experiment, Asymmetric alkenes, Electrophilic addition, Density functional theory