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

KARABIYIK H., OCAK İSKELELİ N., Petek H., Albayrak C., AĞAR E.

JOURNAL OF MOLECULAR STRUCTURE, vol.873, no.1-3, pp.130-136, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 873 Issue: 1-3
  • Publication Date: 2008
  • Doi Number: 10.1016/j.molstruc.2007.03.017
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.130-136
  • Keywords: Schiff base, quinoid, benzenoid, tautomerization, synthon, SCHIFF-BASES, PHOTOCHROMISM, THERMOCHROMISM
  • Dokuz Eylül University Affiliated: Yes

Abstract

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.