Vibrational (FT-IR), electronic (UV-Vis), thermodynamic, and NBO analyses of amide ? imide forms of articaine: a computational perspective on prototropic tautomerism

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dc.authoridDOGAN ULU, OZNUR/0000-0002-5561-227X
dc.contributor.authorSerin, Suemeyya
dc.contributor.authorUlu, Oznur Dogan
dc.date.accessioned2024-08-04T20:54:49Z
dc.date.available2024-08-04T20:54:49Z
dc.date.issued2024
dc.departmentİnönü Üniversitesien_US
dc.description.abstractHerein, the molecular structures of amide <-> imide tautomers of articaine (ART) were computationally investigated at the DFT/B3LYP/6-311++G (d,p) methodology. Experimental FT-IR and UV-Vis characterisation results of ART were compared with the theoretical results of amide (ART-A) and imide (ART-I) forms. Thermodynamic parameters computed for each phase revealed that the amide tautomer of ART was preferred with energy values in the range of 11.9-13.8 kcal/mol. The modification in surface properties as a function of prototropic tautomerism in the ART molecule was studied by electrostatic surface properties (ESP) analysis. Frontier molecular orbital (FMO), natural bond orbital (NBO), and nonlinear optical (NLO) analyses were performed. It is revealed that energy gap values of the ART-I (4.670-4.738 eV) for each phase are slightly higher than those of the corresponding phases in the ART-A (4.515-4.586 eV). Therefore, it can be concluded that the imide form exhibits lower chemical reactivity compared to the amide form. Regarding NLO characteristics, dipole moment (mu(tot)), mean polarisability (alpha(tot)), and mean first-order hyperpolarisability (beta(tot)) values of tautomers have been reported. It was determined that the beta(tot) values computed for ART-A (0.653 x 10(-30) esu) and ART-I (0.710 x 10(-30) esu) were approximately twice the value of the standard urea. [GRAPHICS]en_US
dc.description.sponsorshipThe numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).en_US
dc.description.sponsorshipThe numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).en_US
dc.identifier.doi10.1080/00268976.2023.2279261
dc.identifier.issn0026-8976
dc.identifier.issn1362-3028
dc.identifier.issue10en_US
dc.identifier.scopus2-s2.0-85176279534en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.urihttps://doi.org/10.1080/00268976.2023.2279261
dc.identifier.urihttps://hdl.handle.net/11616/101663
dc.identifier.volume122en_US
dc.identifier.wosWOS:001102360500001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofMolecular Physicsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPrototropic tautomerismen_US
dc.subjectArticaineen_US
dc.subjectReactivityen_US
dc.subjectDFTen_US
dc.subjectNBO analysisen_US
dc.titleVibrational (FT-IR), electronic (UV-Vis), thermodynamic, and NBO analyses of amide ? imide forms of articaine: a computational perspective on prototropic tautomerismen_US
dc.typeArticleen_US

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