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

doi:10.12461/PKU.DXHX202403082

University Chemistry ›› 2024, Vol. 39 ›› Issue (11): 278-285.doi: 10.12461/PKU.DXHX202403082

• Chemistry Laboratory • Previous Articles Next Articles

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 Liu^1,2, Jing Miao^1,2, Huizhe Lu^1,2

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

Abstract

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

Tingbo Wang, Yao Luo, Bingyan Hu, Ruiyuan Liu, Jing Miao, Huizhe Lu. Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment[J].University Chemistry, 2024, 39(11): 278-285.

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

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