Keto-enol tautomerism, conformations and structure of N-(2-hydroxy-5-methylphenyl),2-hydroxybenzaldehydeimine

Kabak M., Elmali A., Elerman Y.

JOURNAL OF MOLECULAR STRUCTURE, cilt.477, sa.1-3, ss.151-158, 1999 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 477 Sayı: 1-3
  • Basım Tarihi: 1999
  • Doi Numarası: 10.1016/s0022-2860(98)00604-8
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.151-158
  • Anahtar Kelimeler: AM1, photochromic, Schiff base, tautomerism, X-ray, SCHIFF-BASES
  • Ankara Üniversitesi Adresli: Hayır

Özet

N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine (C14H13NO2) has been studied by X-ray analysis and AM1 semi-empirical quantum mechanical method. It crystallizes in the monoclinic space group P2(1)/c with a = 7.433(1), b = 9.185(3), c = 186(4) Angstrom, beta = 97.13(1)degrees, V = 1164.3(5) Angstrom(3), Z = 4, D-c = 1.30 gcm(-3) and mu(MoK alpha) = 0.087 mm(-1). The structure was solved by direct methods and refined to R = 0.034 for 1407 reflections [I > 2 sigma(I)]. The title compound is photochromic and the molecule is not planar. Intramolecular hydrogen bonds occur between the pairs of atoms N(1) and O(1) [2.582(1) Angstrom], and N(1) and O2) [2.655(1) Angstrom], the H atom essentially being bonded to the N atom. Adjacent molecules are linked via an intermolecular O-H ... O hydrogen bond [2.582(1) Angstrom] between neighbouring molecules. Tautomeric properties and conformations of the title compound were investigated by semi-empirical quantum mechanical AMI calculations and the results are compared with the X-ray results. (C) 1999 Elsevier Science B.V. All rights reserved.