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

ünver h., Yildiz M., zengin d. m., özbey s., kendi e.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol.31, no.4, pp.211-216, 2001 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 31 Issue: 4
  • Publication Date: 2001
  • Doi Number: 10.1023/a:1014347216821
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.211-216
  • Çanakkale Onsekiz Mart University Affiliated: Yes


N-(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.