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Computational study of phenolic compounds-water clusters

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Abstract

Eight molecules (phenol, o-cresol, m-cresol, p-cresol, pyrocatechol, guaiacol, syringol, and vanillin) were investigated in their one water complex clusters by quantum calculations using B3LYP/cc-pVTZ level of theory. For the first time, the structures of o-cresol, m-cresol, syringol, and vanillin with water were determined. When in contact with water, phenol, cresols, and pyrocatechol present a translinear structure while guaiacol and syringol are in cyclic configurations. It was found that vanillin and water interact via the aldehyde function and the presence of H2O does not affect the intramolecular hydrogen bond in the vanillin structure. The NBO analysis indicates that water electronegativity increases in the structures as follows: translinear < cyclic < vanillin. The HOMO-LUMO energy gap shows that the presence of water increases the hardness of guaiacol and syringol. This phenomenon is probably caused by the cyclic conformations created between water and the phenolic compound.

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  1. Université de Lorraine, Ecole Nationale Supérieure des Industries Chimiques, Laboratoire Réactions et Génie des Procédés (UMR CNRS 7274), 1 rue Grandville, 54000, Nancy, France

    Laëtitia Cesari, Laetitia Canabady-Rochelle & Fabrice Mutelet

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Cesari, L., Canabady-Rochelle, L. & Mutelet, F. Computational study of phenolic compounds-water clusters. Struct Chem 29, 625–643 (2018). https://doi.org/10.1007/s11224-018-1081-9

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