Theoretical and experimental investigation of (E)-2-([3,4-dimethylphenyl)imino]methyl)-3-methoxyphenol: Enol-keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorDemircioglu, Zeynep
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorBuyukgungor, Orhan
dc.date.accessioned2025-03-23T19:40:49Z
dc.date.available2025-03-23T19:40:49Z
dc.date.issued2014
dc.departmentSinop Üniversitesi
dc.description.abstractThe molecular structure and spectroscopic properties of (E)-2-([3,4-dimethylphenyl)iminolmethyl)-3methoxyphenol were investigated by X-ray diffraction, FT-IR and UV-vis spectroscopy. The vibrational frequencies calculatedusing DFT/B3LYP/6-31G(d,p) method. Results showed better agreement with the experimental values. The electronic properties was studied and the most prominent transition corresponds to pi ->pi* and pi ->pi*. Two types of intramolecular hydrogen bonds are strong O-H center dot center dot center dot N interactions in enol-imine form and N-H center dot center dot center dot O interactions in keto-amine form are compared by using density functional theory (DFT) method with B3LYP applying 6-31G(d,p) basis set. Both enol-keto tautomers engender six-membered ring due to intramolecular hydrogen bonded interactions. Geometry optimizations in solvent media were performed with the same level of theory by the polarizable continuum model (PCM). The effect of solvents on the tautomeric stability has been investigated. Stability of the molecule arises from hyperconjugative interactions, charge delocalization and intramolecular hydrogen bond has been analyzed using natural bond orbital (NBO) analysis. Molecular electrostatic potential (MEP) of the titled compound was studied for predicting the reactive sites. Mulliken population method and natural population analysis (NPA) have been studied. Population methods and MEP generally provides information regarding the chemical reactivity regions and charge distributions. Additionally, Frontier Molecular Orbitals analysis hasbeen performed from the optimized geometry. These orbitals also related to ionization potential, electron affinity, kinetic stability and hyperpolarizability of the molecule. The molecule exhibited good nonlinear optical (NLO) activity and first order hyperpolarizability. The predicted nonlinear optical properties of the title compound are 18 times greater than ones of urea. (C) 2014 Elsevier B.V. All rights reserved.
dc.description.sponsorshipFaculty of Arts and Sciences, Ondokuz Mayis University, Turkey [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).
dc.identifier.doi10.1016/j.molstruc.2014.02.062
dc.identifier.endpage222
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-84962339887
dc.identifier.scopusqualityQ1
dc.identifier.startpage210
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2014.02.062
dc.identifier.urihttps://hdl.handle.net/11486/6424
dc.identifier.volume1065
dc.identifier.wosWOS:000335806200028
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Bv
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectNatural population analysis (NPA)
dc.subjectDensity functional theory (DFT)
dc.subjectNonlinear optical properties (NLO)
dc.subjectNatural bond analysis (NBO)
dc.subjectMulliken electronegativity
dc.titleTheoretical and experimental investigation of (E)-2-([3,4-dimethylphenyl)imino]methyl)-3-methoxyphenol: Enol-keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis
dc.typeArticle

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