Intramolecular hydrogen bonding and tautomerism in N-(3-pyridil)-2-oxo-1-naphthylidenemethylamine

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dc.authoridUnver, Huseyin/0000-0003-3968-4385
dc.contributor.authorÜnver, H
dc.contributor.authorYildiz, M
dc.contributor.authorZengin, DM
dc.contributor.authorÖzbey, S
dc.contributor.authorKendi, E
dc.date.accessioned2025-01-27T20:56:20Z
dc.date.available2025-01-27T20:56:20Z
dc.date.issued2001
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractN-(3-pyridil)-2-oxo-1-naphthylidenemethylamine (C16H12N2O) was studied by elemental analysis, IR, H-1 NMR, and UV-visible techniques and X-ray diffraction methods. The UV-visible spectrum of the compound was investigated in solutions effect polarity. The polarity of the some solvents was modifierly the additional (CF3COOH) and [(C2H5)(3)N]. The compound is in tautomeric equilibrium (phenol-imine O-H...N and keto-amine O...H-N forms) in polar and nonpolar solvents. The keto-amine form is observed in basic solutions of DMSO, ethanol, chloroform, benzene, cyclohexane, and in acidic solutions of chloroform and benzene, but not in acidic solutions of DMSO and ethanol. The compound crystallizes in the monoclinic, space group P2(1)/a with a = 7.010(5) Angstrom, b = 13.669(4) Angstrom, c = 12.764(4) Angstrom, beta = 101.23(4)degrees, V = 1199.6(10) Angstrom(3), Z = 4, D-c = 1.375 g/cm(3), mu(MoKalpha) = 0.088 mm(-1), R = 0.045 for 1658 reflections [I > 2sigma(I)]. The title compound is not planar two Schiff base moieties A [C1-C11, O1] and B [N1, C12, C13, N2, C14, C15, C16] are inclined at an angle of 27.4(1)degrees reflecting mainly the twist about C12-N1 [C11-C12-N1-C13, 29.7(2)degrees]. There is a strong intramolecular hydrogen bond (O-H...N) of 2.529(2) Angstrom.
dc.identifier.doi10.1023/A:1014347216821
dc.identifier.endpage216
dc.identifier.issn1074-1542
dc.identifier.issn1572-8854
dc.identifier.issue4
dc.identifier.scopus2-s2.0-18044369509
dc.identifier.scopusqualityQ3
dc.identifier.startpage211
dc.identifier.urihttps://doi.org/10.1023/A:1014347216821
dc.identifier.urihttps://hdl.handle.net/20.500.12428/26373
dc.identifier.volume31
dc.identifier.wosWOS:000175411300005
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofJournal of Chemical Crystallography
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectintramolecular hydrogen bond
dc.subjecttautomerism
dc.subjectspectroscopic and crystallographic studies
dc.subjectcrystal structure
dc.titleIntramolecular hydrogen bonding and tautomerism in N-(3-pyridil)-2-oxo-1-naphthylidenemethylamine
dc.typeArticle

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