Synthesis, DFT computations and antimicrobial activity of a Schiff base derived from 2-hydroxynaphthaldehyde: Remarkable solvent effect

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dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.authoridozdemir, Fethi Ahmet/0000-0001-7215-9692
dc.authoriddayan, osman/0000-0002-0764-1965
dc.contributor.authorTercan, Melek
dc.contributor.authorOzdemir, Namik
dc.contributor.authorOzdemir, Fethi Ahmet
dc.contributor.authorSerbetci, Zafer
dc.contributor.authorErdener, Digdem
dc.contributor.authorCetinkaya, Bekir
dc.contributor.authorDayan, Osman
dc.date.accessioned2025-01-27T20:45:44Z
dc.date.available2025-01-27T20:45:44Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractA new Schiff base bearing sulfonamide group was synthesized and characterized by spectroscopic techniques. Its spectroscopic properties were investigated through density functional theory (DFT/B3LYP) method with the 6-311++G(d,p) basis set theoretically and the zwitterion reversible arrow enol tautomerization was studied using IEF-PCM approximation. The thermodynamic (entropy, enthalpy and Gibbs free energy changes) and energetic quantities of the zwitterion reversible arrow enol tautomerization indicate that the migration of single proton between zwitterion reversible arrow enol tautomer's is unfavored for both directions in all phases. During the change from the water phase to the gas phase, the tautomeric energy barrier increases for the proton transfer reaction from the zwitterion form to the enol form, while the barrier decreases from the enol form to the zwitterion form. On the other hand, experimental studies (UV-vis. and NMR spectroscopies) release that there are two tautomeric species which are the zwitterion form in polar and the enol form in apolar solvents for the soluted compound. Furthermore, the antibacterial effect of the compound was investigated in two different solvents (DMSO and THF) to demonstrate the effect of dominant tautomeric species. The results indicate that the solution in which the enol form is dominant than the zwitterionic form has more antimicrobial efficiency for all bacterial species. (C) 2020 Elsevier B.V. All rights reserved.
dc.description.sponsorshipCanakkale Onsekiz Mart University Scientific Research Projects Commission [FBA-2018-1364]; Ondokuz Mayis University [PYO.FEN.1906.19.001]; Turkish Academy of Science (TUBA)
dc.description.sponsorshipThis research has been supported by Canakkale Onsekiz Mart University Scientific Research Projects Commission (Project No: FBA-2018-1364) and by Ondokuz Mayis University (Project No: PYO.FEN.1906.19.001). We acknowledge Amasya University, Turkey, for having access to GaussView 5.0 and Gaussian 09W program packages. Bekir Cetinkaya thanks the Turkish Academy of Science (TUBA) for support.
dc.identifier.doi10.1016/j.molstruc.2020.127980
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85080115345
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2020.127980
dc.identifier.urihttps://hdl.handle.net/20.500.12428/24701
dc.identifier.volume1209
dc.identifier.wosWOS:000522727600053
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCrystal structure
dc.subjectSpectroscopic analysis
dc.subjectDFT
dc.subjectZwitterion
dc.subjectEnol tautomerism
dc.subjectSolvent effect
dc.subjectAntimicrobial effect
dc.titleSynthesis, DFT computations and antimicrobial activity of a Schiff base derived from 2-hydroxynaphthaldehyde: Remarkable solvent effect
dc.typeArticle

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