Org Biomol Chem
Universidad Nacional Autónoma de México, Instituto de Química, Ciudad Universitaria, Ciudad de México, 04510, Mexico.
Published: August 2021
This contribution explores the bifunctional catalytic activity of water clusters ((HO) with n = 1-5) in organic chemistry similar to that observed in the formation of HSO 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.
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http://dx.doi.org/10.1039/d1ob01026c | DOI Listing |
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