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Updated: Sep 23, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
A DFT study on the mechanism of the sulfonic acid + alcohol esterification reaction
1Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza Pedro Cerbuna 12 E-50009 Zaragoza Spain lsalvate@unizar.es.
Abstract:
Four alternative mechanisms for the benzenesulfonic acid + methanol esterification reaction have been studied at the B3LYP/aug-cc-pVTZ level. The participation of a pentacoordinate sulfur intermediate (in either neutral or protonated form) can be disregarded according to energy considerations. Instead, results show a low activation barrier for the SN1 pathway (through a sulfonylium cation intermediate) and a moderate barrier for the SN2 path (involving protonated methanol as an alkylating reagent).
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