Conformations and structures of N,N'-bis(2-methoxybenzylidene)-1,3-diamino-propanol and N,N'-bis(3-methoxybenzylidene)-1,3-diamino-propanol

KABAK M., Elmali A., Elerman Y., Svoboda I.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, cilt.58, sa.11, ss.1141-1146, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 11
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1515/znb-2003-1118
  • Dergi Adı: ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1141-1146
  • Anahtar Kelimeler: x-ray, schiff base, AM1, photochromism, thermochromism, SCHIFF-BASES, PHOTOCHROMISM, THERMOCHROMISM, MINIMIZATION, GLASSES
  • Ankara Üniversitesi Adresli: Evet

Özet

N,N'-bis(2-methoxybenzylidene)-1,3-diamino-propanol (C19H22N2O4) 1 and N,N'-bis(3-methoxybenzylidene)-1,3-diamino-propanol (C19H22N2O4) 2 have been investigated by X-ray analysis and AMI semi-empirical quantum mechanical method. I is in the monoclinic space group C2/c with a = 33.694(6), b = 6.735(1), c = 17.681(3) Angstrom, beta = 114.72(2)degrees, V = 3645(1) Angstrom(3), Z = 8, D-c = 1.248 mg cm(-3) and mu(Mo-Kalpha) = 0.088 mm(-1). 2 is in the monoclinic space group C2/c with a = 19.173(4), b = 7.626(2), c = 11.788(2) Angstrom, beta = 91.72(2)degrees, V = 1722.8(6) Angstrom(3), Z = 4, D-c = 1.320 mg cm(-3) and mu(Mo-Kalpha) = 0.093 mm(-1). The crystal structures of 1 and 2 were solved by direct methods and refined to R = 0.053 for 1 and R = 0.041 for 2. Both molecules are not planar and 2 has twofold axes on C9 atom. Intramolecular hydrogen bonds occur between O1 and N1 [2.541(3) Angstrom] and between O3 and N2 [2.573(4) Angstrom] atoms for 1 and between O1 and N1 [2.631(2) Angstrom] atoms for 2. The optimized geometries of the crystal structures of 1 and 2 corresponding to non-planar conformation are the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded hydrogen-hydrogen and hydrogen-carbon repulsions.