An intermediate structure trapped in solid-state tautomerization process of (E)-4-[(4-chlorophenylimino)methyl]benzene-1,2,3-triol
✍ Scribed by Hasan Karabıyık; Nazan Ocak-İskeleli; Hande Petek; Çiğdem Albayrak; Erbil Ağar
- Publisher
- Elsevier Science
- Year
- 2008
- Tongue
- English
- Weight
- 367 KB
- Volume
- 873
- Category
- Article
- ISSN
- 0022-2860
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✦ Synopsis
An intermediate structure between the benzenoid and cis-quinoid form of the title compound was trapped in solid-state tautomerization with the aid of OAHÁ Á ÁO 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 ð10Þ supramolecular synthons between the C s 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 OAHÁ Á ÁO type intermolecular H-bonds are fundamental in determining the crystallographically observed conformation of the intermediate structure.