大学化学2025，Vol.40Issue(3)：153-159,7.DOI:10.12461/PKU.DXHX202405172
基于量子化学计算阐明基础化学课程中的Beckmann重排反应机制
Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations
摘要
Abstract
Beckmann rearrangement is a classical reaction in the courses of organic chemistry.However,mainstream textbooks often lack detailed explanations of its reaction mechanism,leaving students with a superficial understanding.This study investigates the Beckmann rearrangement mechanism of three types of ketoxime structures under two different proton sources using quantum chemical calculations.The detailed comparison and analysis provide insights into rearrangement process,including the migration rules of cis-and trans-ketoxime structures.Additionally,the electronic structures of the σ-type and π-type nitrilium ion intermediates are analyzed through frontier molecular orbital theory.This work aims to deepen students'understanding of Beckmann rearrangement and introduce them to the application of theoretical computational chemistry in studying chemical reactions and their underlying mechanisms.关键词
Beckmann重排/DFT计算/反应机理Key words
Beckmann rearrangement/DFT calculations/Reaction mechanism分类
社会科学引用本文复制引用
黄嘉博,黎权鑫,曹中艳,党丽,倪绍飞..基于量子化学计算阐明基础化学课程中的Beckmann重排反应机制[J].大学化学,2025,40(3):153-159,7.基金项目
松山湖实验室开放课题(2023SLABFN16) （2023SLABFN16）
广东省自然科学基金-面上项目(2024A1515010323) （2024A1515010323）
成都大学四川抗菌素工业研究所国际科技合作基地资助(ISTC202204) （ISTC202204）
汕头大学科研启动经费项目(NTF20022) （NTF20022）
