大学化学 >> 2024, Vol. 39 >> Issue (11): 278-285.doi: 10.12461/PKU.DXHX202403082

化学实验 上一篇    下一篇

烯丙基苯基醚Claisen重排反应的量化计算研究——介绍一个计算化学实验

王廷博1, 罗垚1, 胡冰艳1, 刘瑞苑1,2, 苗晶1,2, 路慧哲1,2   

  1. 1 中国农业大学理学院, 北京 100193;
    2 中国农业大学-东抗生物活性分子智能筛选与创制联合实验室, 北京 100193
  • 收稿日期:2024-03-23 录用日期:2024-05-15 发布日期:2024-11-09
  • 通讯作者: 路慧哲 E-mail:Luhz@cau.edu.cn
  • 基金资助:
    2024年度国家级大学生创新创业训练计划项目(202410019033)；国家自然科学基金(22372195)

Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment

Tingbo Wang1, Yao Luo1, Bingyan Hu1, Ruiyuan Liu1,2, Jing Miao1,2, Huizhe Lu1,2   

  1. 1 College of Science, China Agricultural University, Beijing 100193, China;
    2 CAU-East Mab Joint Laboratory for Intelligent Screening and Creation of Active Molecules, Beijing 100093, China
  • Received:2024-03-23 Accepted:2024-05-15 Published:2024-11-09
  • Contact: Huizhe Lu E-mail:Luhz@cau.edu.cn

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摘要： 烯基烯丙基醚或芳基烯丙基醚受热发生[3,3]-σ重排，生成γ,δ-不饱和醛酮或邻对位烯丙基酚，即为Claisen重排反应。本研究利用Gaussian 16程序的DFT方法对烯丙基苯基醚在加热条件的Claisen重排反应进行了量化计算研究。通过本实验的练习，我们旨在加深学生对Claisen重排反应过渡态结构的认识，促进学生应用计算化学工具解决化学问题，提升学生在学习、科研中的实践与创新能力。

关键词: 计算化学实验, Gaussian软件, Claisen重排反应, 烯丙基苯基醚

Abstract: The Claisen rearrangement is a [3,3]-σ rearrangement of allyl ethers or aryl allyl ethers under thermal conditions, leading to the formation of γ,δ-unsaturated aldehydes and ketones or ortho-para-allylphenols. In this study, we employed density functional theory (DFT) within the Gaussian 16 software to perform a quantitative analysis of the Claisen rearrangement of allyl phenyl ether under heating conditions. Through the practice of this experiment, our aim is to deepen students’ understanding of the transition state structure of the Claisen rearrangement reaction, promote the application of computational chemistry tools to solve chemical problems, and enhance students’ practical and innovative abilities in learning and scientific research.

Key words: Computational chemistry experiment, Gaussian software, Claisen rearrangement reaction, Allyl phenyl ether