Computational study of phenolic compounds-water clusters

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 pyrocat-echol 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 H 2 O 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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https://hal.univ-lorraine.fr/hal-01934447
Contributor : Fabrice Mutelet <>
Submitted on : Monday, November 26, 2018 - 8:21:12 AM
Last modification on : Thursday, September 12, 2019 - 1:00:50 AM

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Laetitia Cesari, Laetitia Canabady-Rochelle, Fabrice Mutelet. Computational study of phenolic compounds-water clusters. Structural Chemistry, Springer Verlag (Germany), 2018, 29 (2), pp.625 - 643. ⟨10.1007/s11224-018-1081-9⟩. ⟨hal-01934447⟩

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