An intermediate structure trapped in solid-state tautomerization process of (E)-4-[(4-chlorophenylimino)methyl]benzene-1,2,3-triol

KARABIYIK H., Ocak İskeleli N., Petek H., Albayrak C., Ağar E.

JOURNAL OF MOLECULAR STRUCTURE, cilt.873, sa.1-3, ss.130-136, 2008 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 873 Sayı: 1-3
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1016/j.molstruc.2007.03.017
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.130-136
  • Anahtar Kelimeler: Schiff base, quinoid, benzenoid, tautomerization, synthon, SCHIFF-BASES, PHOTOCHROMISM, THERMOCHROMISM
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

An intermediate structure between the benzenoid and cis-quinoid form of the title compound was trapped in solid-state tautomerization with the aid of O-H center dot center dot center dot O type intermolecular H-bonds leading to multi-point self-recognition. X-ray crystallographic study reveals that an interesting extended structure, H-bonded polymeric chain, is formed by linking pseudocyclic centrosymmetric R-2(2)(10) supramo lecular synthons between the C, symmetry monomer units. In order to better understand structural features in solid state, ab initio quantum chemical calculations at level of RHF/6-31G* were performed in both gas-phase and the extended structure containing five dimers. The results from the computational studies suggest that the gas-phase conformation of the title compound that closely matches the crystal structure corresponds to a local energy minimum between its benzenoid and cis-quinoid form and the O-H center dot center dot center dot O type intermolecular H-bonds are fundamental in determining the crystallographically observed conformation of the intermediate structure. (c) 2007 Elsevier B.V. All rights reserved.