大学化学 >> 2023, Vol. 38 >> Issue (10): 258-265.doi: 10.3866/PKU.DXHX202301016

化学实验 上一篇    下一篇

Baeyer-Villiger重排机理及基团迁移规律的量子化学计算研究——推荐一个研究型计算化学实验

朱荣秀(), 郭今心, 杨一莹, 张冬菊()   

  • 收稿日期:2023-01-12 录用日期:2023-03-01 发布日期:2023-03-30
  • 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);山东大学教育教学改革研究项目(2022Y076)

Quantum Chemical Calculation Study of the Mechanism and Migratory Aptitude of the Baeyer-Villiger Rearrangement: Recommending a Research-Oriented Computational Chemistry Experiment

Rongxiu Zhu(), Jinxin Guo, Yiying Yang, Dongju Zhang()   

  • Received:2023-01-12 Accepted:2023-03-01 Published:2023-03-30
  • Contact: Rongxiu Zhu, Dongju Zhang E-mail:rxzhu@sdu.edu.cn;zhangdj@sdu.edu.cn

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摘要：

介绍一个面向高年级本科生的研究型计算化学实验。Baeyer-Villiger (B-V)重排是有机合成中最基本的反应类型之一，是有机化学课程的重要教学内容，但人们对B-V重排迁移规律的认识存在争议。这种争议在课堂教学中常被忽视。本实验利用高斯计算软件，通过量子化学计算分析了B-V反应的微观机制和基团的迁移规律。本实验旨在训练学生使用化学计算方法开展科学研究的基本思路，培养学生批判性思维能力，提升学生的科研素养。

关键词: B-V重排, 反应机理, 迁移能力, 密度泛函理论计算

Abstract:

This work describes a research-oriented computational chemistry experiment for senior undergraduates. The Baeyer-Villiger (B-V) reaction is one of the most useful reactions in organic chemistry, and is also an important teaching topic, yet the migratory aptitude of the various substituents is still debatable and these controversies are often neglected during the teaching and learning process. In this experiment, the reaction mechanism and migratory aptitude of the B-V rearrangement are studied by performing quantum chemistry calculations with the Gaussian program. The purposes of this experiment are to train students to conduct scientific research using chemical computational methods, cultivate students' critical thinking ability, and improve students' scientific research literacy.

Key words: B-V rearrangement, Reaction mechanism, Migratory aptitude, DFT calculations