酸催化羧酸与醇酯化反应的计算化学研究

doi:10.12461/PKU.DXHX202405072

Abstract

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: Esterification reaction, Carboxylic acid, Alcohol, Reaction mechanism, Quantum chemical calculations

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.

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

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