Issue 31, 2021

Water clusters as bifunctional catalysts in organic chemistry: the hydrolysis of oxirane and its methyl derivatives

Abstract

This contribution explores the bifunctional catalytic activity of water clusters ((H2O)n with n = 1–5) in organic chemistry similar to that observed in the formation of H2SO4 in acid rain (Chem. Commun., 53, 3516, (2017)). We considered for this purpose the Hydrolysis of Epoxides (HE), in particular, that of oxirane and its methyl derivatives. Surrounding water molecules with H-bond cooperative effects decrease the activation energy of the rate-limiting step of HE in condensed phase, especially when they lead to an anti-periplanar attack on the alkoxide leaving group. Furthermore, the water molecules have a bifunctional catalytic role in HE by (i) increasing the nucleophilic and electrophilic character of the attacking oxygen atom and the leaving group of the reaction, respectively, and (ii) placing the reactants in a suitable disposition for the substitution to occur. Overall, this investigation provides relevant insights into the collective action of water molecules on organic reactions in neutral, basic and acid media.

Graphical abstract: Water clusters as bifunctional catalysts in organic chemistry: the hydrolysis of oxirane and its methyl derivatives

Supplementary files

Article information

Article type
Communication
Submitted
29 6月 2021
Accepted
13 7月 2021
First published
15 7月 2021

Org. Biomol. Chem., 2021,19, 6776-6780

Water clusters as bifunctional catalysts in organic chemistry: the hydrolysis of oxirane and its methyl derivatives

A. Sauza-de la Vega, H. Salazar-Lozas, W. E. Vallejo Narváez, M. Hernández-Rodríguez and T. Rocha-Rinza, Org. Biomol. Chem., 2021, 19, 6776 DOI: 10.1039/D1OB01026C

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