Authors: S.V. Puchkov, Yu.V. Nepomnyashchikh

Title of the article: Evaluation of monohydric and polyhydric alcohols reactivity in the esterification by quantum chemical methods

Year: 2023, Issue: 3, Pages: 52-59

Branch of knowledge: 2.6.10. Organic matter technology

Index UDK: 544.43:547-316

DOI: 10.26730/1999-4125-2023-3-52-59

Abstract: For 12 monohydric alcohols of methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-2-propanol (tert-butyl alcohol), 1-pentanol, 2,2-dimethyl-1-propanol, 1-hexanol, 2-hexanol, 3-hexanol, cyclohexanol in the "chair" and "boat" conformations and 5 polyatomic – 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,2,3-propantriol (glycerin) and pentaerythritol the effective charges on oxygen atoms were calculated. It is shown that with a decrease in the value of the negative charge on the oxygen atom of the hydroxyl group of monohydric alcohols, the rate of their esterification by carboxylic acids increases. The nature of the influence of the magnitude of the negative charge on the oxygen atom of alcohols on the speed of the limiting stages of esterification and hydrolysis is estimated. It has been found that for polyhydric alcohols, the same correlation remains between the magnitude of the negative charge on the oxygen atom of the hydroxyl group and the reactivity of these groups in esterification reactions as for primary monohydric alcohols. The revealed dependencies allow a comparative assessment of the reactivity of alcohols in esterification reactions.

Key words: alcohols quantum chemical methods effective charges esterification hydrolysis reactivity

Receiving date: 05.04.2023

Approval date: 15.06.2023

Publication date: 30.06.2023

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