Computational study on the molecular conformations of phenolic compounds

The study of the conformation of eight phenolic compounds (i.e. phenol, guaiacol, syringol, pyrocatechol, o-, m-, p-cresol and vanillin) was carried out using B3LYP (Becke, 3-parameter, Lee-Yan-Parr) method and cc-pVTZ (correlation consistent polarized polarisation Valence triple zêta) basis set. Po...

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Bibliographic Details
Published in:Structural chemistry 2018-02, Vol.29 (1), p.179-194
Main Authors: Cesari, Laëtitia, Canabady-Rochelle, Laetitia, Mutelet, Fabrice
Format: Article
Language:English
Subjects:
Benzene
Chemical bonds
Chemical Sciences
Chemistry
Chemistry and Materials Science
Computer Applications in Chemistry
Engineering Sciences
Hydrogen bonding
Hydrogen bonds
Hydrogen-based energy
Mathematical analysis
Original Research
Phenols
Physical Chemistry
Potential energy
Theoretical and Computational Chemistry
Vanillin
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Summary:The study of the conformation of eight phenolic compounds (i.e. phenol, guaiacol, syringol, pyrocatechol, o-, m-, p-cresol and vanillin) was carried out using B3LYP (Becke, 3-parameter, Lee-Yan-Parr) method and cc-pVTZ (correlation consistent polarized polarisation Valence triple zêta) basis set. Potential energy surfaces were plotted in order to identify the minimum energy structures and the transition states. For the first time, structures of vanillin and syringol were completely determined. Moreover, our work also confirms that the most stable conformations of m-cresol and p-cresol are obtained when the methyl group presents a hydrogen atom at the perpendicular of the benzene ring. The possibility of intramolecular hydrogen bonding was also investigated. Guaiacol, pyrocatechol, syringol and vanillin present a structure stabilized by the presence of a moderate hydrogen bond. Finally, potential energy barriers and rotational potential functions were calculated. The comparison of the rotational potential parameters for each molecule highlights the presence of similarities specific to each substituent and their neighbours.
ISSN:1040-0400
1572-9001
DOI:10.1007/s11224-017-1017-9