酸催化羧酸与醇酯化反应的计算化学研究

引用本文: 冯爱利, 陆鑫, 刘鹏, 张冬菊. 酸催化羧酸与醇酯化反应的计算化学研究[J]. 大学化学, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072 shu

Citation: Aili Feng, Xin Lu, Peng Liu, Dongju Zhang. Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols[J]. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072 shu

酸催化羧酸与醇酯化反应的计算化学研究

冯爱利 ^1, ,
陆鑫 ^1, ,
刘鹏 ^{2,
,} ,
张冬菊 ^{1,
,}

1.
山东大学化学与化工学院, 济南 250100;
2.
曲阜师范大学化学与化工学院, 山东曲阜 273165

通讯作者: 刘鹏,E-mail:liupeng@qfnu.edu.cn; 张冬菊,E-mail:zhangdj@sdu.edu.cn

基金项目:
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(Z2022024,Z2022169)；山东大学教育教学改革研究项目(2024Z07,2023Y061,2023Y102)；济南市科技局“新高校20条”项目

摘要: 酯化反应是一类重要的化学反应类型，通常指醇与羧酸在酸催化下脱水生成酯的反应。本文以几个典型的酯化反应为例，通过量子化学计算，在分子层次上深入探讨了加成-消除、碳正离子和酰基正离子等三种常见的酯化反应机理，分析了反应的热力学和动力学性质。计算结果为理解有机化学教材中关于酯化反应的定性描述，如“酯化反应机理与羧酸和醇的类型有关”“酯化反应中酸脱羟基醇脱氢”“酯化反应速度较慢且为可逆反应”等，提供了直观物理图像和定量支持，有助于学生更深入全面地理解酯化反应。本文可作为引导本科生学习计算化学的教学案例，突出计算化学在解析物质结构与性能关系方面的重要作用。

关键词:

English

Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols

Aili Feng ^1, ,
Xin Lu ^1, ,
Peng Liu ^{2,
,} ,
Dongju Zhang ^{1,
,}

1.
School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;
2.
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong Province, China

Corresponding author: Peng Liu, ; Dongju Zhang,

Received Date: 07 May 2024
Revised Date: 27 September 2024
Available Online: 13 January 2025

Abstract: Esterification reactions are an important class of chemical reactions, typically involving the reaction between alcohols and carboxylic acids under acid catalysis to form esters via dehydration. This paper uses several typical esterification reactions as examples and explore three common esterification mechanisms at the molecular level: addition-elimination, carbocation, and acyl cation mechanisms. Both the thermodynamic and kinetic properties of the reactions are examined. The calculated results provide intuitive physical images and quantitative support for understanding qualitative descriptions of esterification reactions found in organic chemistry textbooks, such as “The mechanism of esterification reaction depends on the types of carboxylic acids and alcohols”, “The acid eliminates the hydroxyl group, and the alcohol loses a hydrogen atom in esterification reaction”, and “Esterification reactions are slow and reversible”. These findings offer students a deeper, more comprehensive understanding of esterification reactions. This paper can serve as a teaching case to guide undergraduates in learning computational chemistry, emphasizing the important role of computational chemistry in elucidating the relationship between molecular structures and properties.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

酸催化羧酸与醇酯化反应的计算化学研究

通讯作者: 刘鹏,E-mail:liupeng@qfnu.edu.cn; 张冬菊,E-mail:zhangdj@sdu.edu.cn

English

Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols

Corresponding author: Peng Liu, ; Dongju Zhang,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

酸催化羧酸与醇酯化反应的计算化学研究

通讯作者: 刘鹏,E-mail:liupeng@qfnu.edu.cn; 张冬菊,E-mail:zhangdj@sdu.edu.cn

English

Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols

Corresponding author: Peng Liu, ; Dongju Zhang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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