Theoretical and Experimental Studies on Electronic Structure, Cocrystallization, and Intramolecular Proton Transfer of Two Tautomers: (E)-2-{[2-(Hydroxymethyl)phenylimino]methyl}-5-methoxyphenol and (z)-6-{[2-(Hydroxymethyl)phenylamino] methylene}-3-methoxy-cyclohexa-2,4-dienone

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorKosar, Basak
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorOdabasoglu, Mustafa
dc.contributor.authorBuyukgungor, Orhan
dc.date.accessioned2025-03-23T19:47:07Z
dc.date.available2025-03-23T19:47:07Z
dc.date.issued2011
dc.departmentSinop Üniversitesi
dc.description.abstractIn this work, the structure of (E)- 2-{[2-(hydroxymethyl) phenylimino] methyl}-5-methoxyphenol was characterized by X-ray single crystal diffraction technique, infrared spectroscopy, and quantum chemical computational methods as both experimental and theoretically. The compound crystallizes in the triclinic space group P1 with a = 9.4601 (5) angstrom, b = 11.7273 (7) angstrom, c = 12.4400 (8) angstrom, alpha = 88.179 (5)degrees, b = 71.442 (4)degrees, gamma = 84.977 (5)degrees, and Z = 4. X-Ray study shows that both enol-imine and keto-amine tautomeric forms coexist in the asymmetric unit as two independent molecules. The molecular geometry was also optimizedat the B3LYP/6-311G(d,p) level by using density functional theory started from the crystallographically achieved parameters of molecule. From the optimized geometry of the molecule, molecular electrostatic potential was evaluated, frontier molecular orbitals and natural bond orbital analysis were performed, and vibrational frequencies were computed theoretically. The polarizable continuum model calculations starting from the optimized geometry were also carried out in both gaseous and solution phase to investigate the energetic behavior and dipole moment of the title compound with the same level of theory. (C) 2010 Wiley Periodicals, Inc. Int J Quantum Chem 111: 3654-3663, 2011
dc.description.sponsorshipUniversity Research Fund [F. 279]
dc.description.sponsorshipThe authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the STOE IPDS 2 diffractometer (purchased under grant F. 279 of the University Research Fund). CCDC 760093 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033.
dc.identifier.doi10.1002/qua.22789
dc.identifier.endpage3663
dc.identifier.issn0020-7608
dc.identifier.issn1097-461X
dc.identifier.issue14
dc.identifier.scopus2-s2.0-79952185614
dc.identifier.scopusqualityQ2
dc.identifier.startpage3654
dc.identifier.urihttps://doi.org/10.1002/qua.22789
dc.identifier.urihttps://hdl.handle.net/11486/7288
dc.identifier.volume111
dc.identifier.wosWOS:000295366300020
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofInternational Journal of Quantum Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectdensity functional theory (DFT)
dc.subjectX-ray crystal structure
dc.subjectnatural bond orbitals (NBO)
dc.subjectmolecular electrostatic potential (MEP)
dc.subjectketo-enol tautomerism
dc.titleTheoretical and Experimental Studies on Electronic Structure, Cocrystallization, and Intramolecular Proton Transfer of Two Tautomers: (E)-2-{[2-(Hydroxymethyl)phenylimino]methyl}-5-methoxyphenol and (z)-6-{[2-(Hydroxymethyl)phenylamino] methylene}-3-methoxy-cyclohexa-2,4-dienone
dc.typeArticle

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