Intramolecular hydrogen bonding and tautomerism in Schiff bases.: Structure of N-(2-pyridil)-2-oxo-1-naphthylidenemethylamine

Basit Öğe Kaydı
dc.authoridNAZIR, HASAN/0000-0002-8423-751X
dc.authoridTahir, Dr. Muhammad Nawaz/0000-0002-6815-9806
dc.contributor.authorNazir, H
dc.contributor.authorYildiz, M
dc.contributor.authorYilmaz, H
dc.contributor.authorTahir, MN
dc.contributor.authorÜlkü, D
dc.date.accessioned2025-01-27T20:24:23Z
dc.date.available2025-01-27T20:24:23Z
dc.date.issued2000
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractN-(2-pyridil)-salicylidene (1) and N-(2-pyridil)-2-oxo-1-naphthylidene-methylamine (2) were studied by elemental analysis, IR, H-1 NMR and UV-visible techniques and the structure of compound (2) was examined crystallographically. The UV-visible spectra of 2-hydroxy Schiff bases are investigated in different solvents, acidic and basic media. Compound (2) is in tautomeric equilibrium (phenol-imine, O-H ... N reversible arrow keto-amine, O ... H-N forms) in polar and non-polar solvents. These tautomers are not observed in polar and non-polar solvents for (1) as also supported by H-1 NMR and UV-visible data. The keto-amine form of compound (2) was 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. On the contrary, this form for compound (1) was not observed in the same solutions. The asymmetric unit of compound (2) contains two independent molecules of (C16H12N2O) which constitute a tautomeric pair. The observed differences in the related C=N (1.317(4) and 1.330(4) Angstrom) and C-O (1.279(4) and 1.263(4) Angstrom) bond lengths in the two crystallographically independent molecules indicate that the phenol-imine and the keto-amine forms coexist in the solid state. Intramolecular hydrogen bond lengths (O-H ... N) are 2.586(4) Angstrom and 2.518(4) Angstrom for the two individual tautomers. It crystallizes in the monoclinic space group P2(1)/n with a = 5.837(2), b = 17.476(2), c = 24.295(3) Angstrom, beta = 91.95(4)degrees, V = 2476.9(6) Angstrom(3), Z = 4 and Dx = 1.3315 g cm(-3). (C) 2000 Elsevier Science B.V. All rights reserved.
dc.identifier.doi10.1016/S0022-2860(00)00393-8
dc.identifier.endpage250
dc.identifier.issn0022-2860
dc.identifier.scopus2-s2.0-0034643911
dc.identifier.scopusqualityQ1
dc.identifier.startpage241
dc.identifier.urihttps://doi.org/10.1016/S0022-2860(00)00393-8
dc.identifier.urihttps://hdl.handle.net/20.500.12428/22191
dc.identifier.volume524
dc.identifier.wosWOS:000087092000021
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Bv
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.subjectSchiff bases
dc.subjecttautomerism
dc.subjectspectroscopic and crystallographic studies
dc.subjectintramolecular hydrogen bond
dc.titleIntramolecular hydrogen bonding and tautomerism in Schiff bases.: Structure of N-(2-pyridil)-2-oxo-1-naphthylidenemethylamine
dc.typeArticle

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu