Concomitant polymorphism of a pyridine-2,6-dicarboxamide derivative in a single space group: Experimental and molecular modeling study

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dc.authoridOzdemir, Namik/0000-0003-3371-9874
dc.authoriddayan, osman/0000-0002-0764-1965
dc.authoridCetinkaya, Bekir/0000-0002-4551-8650
dc.contributor.authorOzdemir, Namik
dc.contributor.authorDayan, Osman
dc.contributor.authorCetinkaya, Bekir
dc.contributor.authorAkgul, Cahit
dc.date.accessioned2025-01-27T20:29:04Z
dc.date.available2025-01-27T20:29:04Z
dc.date.issued2012
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe title compound, N-2,N-6-bis{2-[(Z)-2-hydroxybenzylideneamino]phenyl}pyridine-2,6-dicarboxamide (3), has been synthesized by the reaction of 2-{(2-aminophenylimino)methyl}phenol (1) with pyridine2,6-dicarbonyl dichloride (2), and characterized by elemental analysis. FT-IR and NMR spectroscopies and thermal analysis. Compounds 1 and 3 were evaluated for their antibacterial activities against Grampositive and Gram-negative bacteria. The catalytic activity of 3 was also studied, and as a result, the in situ prepared three component system Ru(II)/3/KOH is shown to be an efficient catalyst for the transfer hydrogenation reaction of various ketones under mild conditions. Compound 3 has been crystallized in two polymorphic forms under the same conditions, and their crystal structures have been determined using single crystal X-ray diffraction technique. The molecular geometry, vibrational frequencies and gauge-independent atomic orbital (CIAO) H-1 and C-13 NMR chemical shift values of 3 in the ground state have been calculated using the density functional theory (DFT/B3LYP) method with the 6-31G(d) basis set, and compared with the experimental data. The results are in good agreement with experimental data. The effect of different solvents on the geometry, vibrational frequencies, total energies and dipole moments was also studied using the same method by applying the Onsager Model. There are subtle differences in the conformations and packing of the two polymorphs as a consequence of intermolecular hydrogen bonding interactions. Therefore, DFT calculations for the hydrogen bond interactions in the polymorphs were carried out using same basis set. The changes of thermodynamic properties from the monomers to 3 with the temperature ranging from 200 K to 400 K have been obtained using the statistical thermodynamic method. (C) 2011 Elsevier B.V. All rights reserved.
dc.description.sponsorshipScientific and Technical Research Council of Turkey (TUBITAK) [107T808]; Canakkale Onsekiz Mart University Scientific Research Projects Commission [2009-16]; University Research Fund [F-279]
dc.description.sponsorshipThis research has been supported by The Scientific and Technical Research Council of Turkey (TUBITAK) (Project No: 107T808) and Canakkale Onsekiz Mart University Scientific Research Projects Commission (Project No: 2009-16). We thank Prof. Ismet Kaya for thermal analyses and helpful discussions. We also thank Prof. Dr. Orhan Buyukgungor for his help with the data collection and acknowledge the Faculty of Arts and Sciences, Ondokuz May's University, Turkey, for the use of the STOE IPDS II diffractometer (purchased under grant No. F-279 of the University Research Fund).
dc.identifier.doi10.1016/j.saa.2011.11.026
dc.identifier.endpage624
dc.identifier.issn1386-1425
dc.identifier.issn1873-3557
dc.identifier.pmid22137748
dc.identifier.scopus2-s2.0-83655192945
dc.identifier.scopusqualityQ1
dc.identifier.startpage614
dc.identifier.urihttps://doi.org/10.1016/j.saa.2011.11.026
dc.identifier.urihttps://hdl.handle.net/20.500.12428/22803
dc.identifier.volume86
dc.identifier.wosWOS:000300515500088
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofSpectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCrystal structure
dc.subjectIRand NMR spectroscopy
dc.subjectDensity functional theory method (OFT)
dc.subjectSolvent effect
dc.subjectTransfer hydrogenation
dc.subjectEntropy-enthalpy compensation
dc.titleConcomitant polymorphism of a pyridine-2,6-dicarboxamide derivative in a single space group: Experimental and molecular modeling study
dc.typeArticle

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