Molecular structure and conformation of N-2-[3 '-(methoxysalicylideneimino)benzyl]-3 ''-methoxysalicylideneimine

Dey D., Dey S., Elmali A., Elerman Y.

JOURNAL OF MOLECULAR STRUCTURE, cilt.562, sa.1-3, ss.177-184, 2001 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 562 Sayı: 1-3
  • Basım Tarihi: 2001
  • Doi Numarası: 10.1016/s0022-2860(00)00970-4
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.177-184
  • Anahtar Kelimeler: X-ray, Schiff base, AM1, photochromism, thermochromism, CRYSTAL-STRUCTURE, SCHIFF-BASES, PHOTOCHROMISM, THERMOCHROMISM, TOPOCHEMISTRY, MINIMIZATION, COMPLEXES, GLASSES
  • Ankara Üniversitesi Adresli: Hayır

Özet

The Schiff base, N-2-[3 '-(methoxysalicylideneimino)benzyl]-3 " -methoxysalicylidene-imine 1,2-C6H4[N=CHC6H3(OMe-3 ' )OH-2 ' ]CH2N=CHC6H3(OMe-3 " )OH-2 ", has been prepared by the reaction of 2-amino-1-benzylamine and 3-methoxysalicylaldehyde (o-vanillin) in ethanol. The molecular structure has been confirmed by single crystal X-ray crystallography. The crystal is in the monoclinic space group P2(1)/n with a=16.179(5), b=6.715(5), c=18.780(6)Angstrom, beta = 100.56(3)degrees, D-calc = 1.293 mg cm(-3), V= 2006(2) Angstrom (3) and R = 0.0357 for 3929 independent reflections. The H-1 and C-13 NMR spectra in CDCl3 solution indicate the retention of solid state structure in solution. The title compound is not planar. Intramolecular hydrogen bonds occur between O(1) and N(1) [2.614(2) Angstrom] and between O(2) and N(2) [2.585(2) Angstrom] atoms, the hydrogen atom essentially being bonded to the oxygen atom. Minimum energy conformations from AM1 were calculated as a function of five torsion angles theta (1) (C6-C7-N1-C8), theta (2) (C14-N2-C15-C16), theta (3) (C9-C8-N1-C7), theta (4) (C13-C14-N2-C15) and theta (5) (C10-C9-C8-N1), varied every 5 degrees. The optimized geometry of the crystal structure corresponding to the non-planar conformation is the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded hydrogen-hydrogen repulsions. (C) 2001 Elsevier Science B.V. All rights reserved.