大学化学 >> 2023, Vol. 38 >> Issue (11): 249-255.doi: 10.3866/PKU.DXHX202303035

师生笔谈 上一篇    下一篇

基于HMO方法、FMO理论和DFT计算理解Diels-Alder反应的立体专一性、区域选择性和立体选择性

李唯加, 柳凯, 王一翔, 张志君, 杨一莹(), 张冬菊()   

  • 收稿日期:2023-03-09 录用日期:2023-05-18 发布日期:2023-05-26
  • 通讯作者: 杨一莹,张冬菊 E-mail:yiyingyang@sdu.edu.cn;zhangdj@sdu.edu.cn
  • 作者简介:第一联系人：

    †共同第一作者，对本工作有同等贡献

  • 基金资助:
    国家自然科学基金(22273051);国家自然科学基金(22003032);山东省高等教育本科教学改革研究项目(Z2022169);山东省自然科学基金青年基金项目(ZR2020QB077);山东大学教育教学改革研究项目(2022Y072)

Exploring Stereospecificity, Regioselectivity, and Stereoselectivity in Diels-Alder Reactions: Insights from HMO Method, FMO Theory, and DFT Calculations

Weijia Li, Kai Liu, Yixiang Wang, Zhijun Zhang, Yiying Yang(), Dongju Zhang()   

  • Received:2023-03-09 Accepted:2023-05-18 Published:2023-05-26
  • Contact: Yiying Yang, Dongju Zhang E-mail:yiyingyang@sdu.edu.cn;zhangdj@sdu.edu.cn

RichHTML

44

PDF

2000

赞

摘要：

Diels-Alder (D-A)反应是基础有机化学的重要教学内容，也是结构化学中运用物质结构基本原理予以分析处理的典型化学反应。本文基于休克尔分子轨道(HMO)方法、前线分子轨道(FMO)理论和量子化学计算研究了1-甲氧基-1,3-丁二烯和丙烯醛的Diels-Alder反应，给出了理解反应立体专一性、区域选择性和立体选择性的定量信息和直观物理图像。研究结果有助于加深学生对D-A反应特点和规律的认识、培养学生对计算化学的兴趣、提高学生分析问题和解决问题的能力。

关键词: Diels-Alder反应, 立体专一性, 区域选择性, 立体选择性, DFT计算

Abstract:

The Diels Alder (D-A) reaction represents a crucial component of fundamental organic chemistry education and serves as a quintessential example of structural chemistry analyzed via basic principles of chemical sciences. This study explores the Diels-Alder reaction involving 1-methoxy-1,3-butadiene and acrolein, utilizing tools such as the Hückel molecular orbital (HMO) method, frontier molecular orbital (FMO) theory, and quantum chemical calculations. This approach provides detailed quantitative data and intuitive visual illustrations to elucidate the stereospecificity, regioselectivity, and stereoselectivity inherent to this reaction. The findings from this study serve as valuable resources for students, not only enhancing their understanding of D-A reaction properties and principles, but also developing their interest in computational chemistry and augmenting their problem-solving acumen.

Key words: Diels-Alder reaction, Stereospecificity, Regioselectivity, Stereoselectivity, DFT calculations