芳香化合物磺化反应机理的计算化学研究  

Computational Chemistry Study on the Sulfonation Reaction Mechanism of Aromatic Compounds

作　　者：孙悦竹 杨一莹 张冬菊[1] SUN Yue-Zhu;YANG Yi-Ying;ZHANG Dong-Ju(School of Chemistry and Chemical Engineering,Shandong University,Jinan 250100,China)

机构地区：[1]山东大学化学与化工学院,山东济南250100

出　　处：《化学教育（中英文）》2024年第10期100-104,共5页Chinese Journal of Chemical Education

基　　金：国家自然科学基金(22273051);山东省高等教育本科教学改革研究项目(Z2022169);山东大学教育教学改革研究项目(2022Y072);山东大学研究生教育优质课程项目。

摘　　要：磺化反应是芳香化合物最重要的反应类型之一。最新理论研究表明,磺化反应一般遵循三分子反应机理,这与有机化学教材中描述的双分子机理有明显区别。以甲苯的磺化反应为例,通过密度泛函理论计算研究了磺化反应的分子机理、区域选择性以及溶剂对反应性能的影响,并通过比较苯、甲苯和硝基苯磺化反应的计算结果,分析了取代基对磺化反应性能的影响。旨在通过对模型反应的计算化学研究,及时更新并深化对磺化反应机理的理解,进而提高相关教学内容的创新性、高阶性和挑战度。Sulfonation reactions are one of the most significant reaction types for aromatic compounds.Recent theoretical studies have shown that sulfonation reactions generally follow a trimolecular reaction mechanism,which differs significantly from the described bimolecular mechanism in organic chemistry textbooks.In this study,using density functional theory calculations,the sulfonation reaction of toluene is investigated as an example to study the molecular mechanism,regioselectivity,and the influence of solvents on the reaction performance.By comparing the computational results of the sulfonation reactions of benzene,toluene,and nitrobenzene,the effects of substituents on the sulfonation reaction performance are analyzed.The aim of this paper is to present the latest advances in understanding the mechanism of sulfonation reactions through computational chemistry studies on the model reactions,thereby enhancing the innovation,high order,and challenge of related teaching materials.

关 键 词：芳香化合物 磺化反应 反应机理 密度泛函理论 

分 类 号：G642.0[文化科学—高等教育学] O621.25-4[文化科学—教育学]