大学化学 >> 2023, Vol. 38 >> Issue (8): 299-304.doi: 10.3866/PKU.DXHX202209092

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理论与计算化学在基础化学课程中的应用：1,2-环氧化物开环反应

赵容浩, 黄职钱, 杨一莹, 朱荣秀(), 张冬菊()   

  • 收稿日期:2022-09-30 录用日期:2022-11-03 发布日期:2023-01-03
  • 通讯作者: 朱荣秀,张冬菊 E-mail:rxzhu@sdu.edu.cn;zhangdj@sdu.edu.cn
  • 基金资助:
    山东省本科教学改革研究项目“计算化学在大学基础化学教学中的应用”;山东大学教育教学改革研究项目(2022Y072);山东省自然科学基金青年基金项目(ZR2020QB077)

Application of Theoretical and Computational Chemistry in General Chemistry Curriculum: Ring-opening Reactions of 1,2-Epoxides

Ronghao Zhao, Zhiqian Huang, Yiying Yang, Rongxiu Zhu(), Dongju Zhang()   

  • Received:2022-09-30 Accepted:2022-11-03 Published:2023-01-03
  • Contact: Rongxiu Zhu, Dongju Zhang E-mail:rxzhu@sdu.edu.cn;zhangdj@sdu.edu.cn

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摘要：

1,2-环氧化物开环反应是化学类各专业有机化学课程中的重要教学内容，教材中的描述缺少定量、直观信息，学生通常采用机械记忆方式予以学习，不能完全理解相关的反应机制。本文设计了一个用理论化学方法研究化学反应的典型案例，通过量子化学计算探讨了酸、碱催化1,2-环氧化物开环反应的分子机制，揭示了反应的热力学和动力学性质，描绘了反应过程的直观物理图像，给出了理解反应区域选择性的定量信息。论文将计算量子化学与有机化学教学内容有机融合，不仅有助于学生加深对化学基本概念和基础理论的理解，而且有助于学生开阔视野、拓展思路，使学生充分认识到理论计算是开展化学研究的重要手段。

关键词: 1, 2-环氧化物, 开环反应, 甲醇, 量子化学计算

Abstract:

The ring-opening reactions of 1,2-epoxides are important topics in organic chemistry courses. The description of the ring-opening reaction of epoxides in textbooks lacks quantitative and visual information; therefore, students usually learn it by rote and cannot fully understand the mechanisms involved. This experiment presents a prototypical example of investigating the molecular mechanism of a chemical reaction using theoretical chemistry methods. By carrying out quantum chemical calculations on the ring-opening reactions of a typical 1,2-epoxide catalyzed by an acid or base, we reveal the thermodynamic and kinetic properties of the reaction and provide an intuitive physical picture and quantitative information of the reaction for understanding the regioselectivity of the reaction. This experiment will not only help students deepen their understanding of the basic concepts and theories of chemistry but also help them broaden their horizons and expand their thinking, making them realize that theoretical calculation is an important tool in chemical research.

Key words: 1, 2-Epoxides, Ring-opening reactions, Methanol, Quantum chemical calculations