A comparative study of the crystal structures of tetrahalogenated hydroquinones and γ-hydroquinone

Thalladi, V. R. ; Weiss, H. C. ; Boese, R. ; Nangia, A. ; Desiraju, G. R. (1999) A comparative study of the crystal structures of tetrahalogenated hydroquinones and γ-hydroquinone Acta Crystallographica Section B: Structural Science, 55 . pp. 1005-1013. ISSN 0108-7681

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Official URL: http://scripts.iucr.org/cgi-bin/paper?S01087681990...

Related URL: http://dx.doi.org/10.1107/S0108768199005911

Abstract

γ-Hydroquinone (1) and its tetrafluoro, tetrachloro and tetrabromo derivatives (2), (3) and (4) adopt crystal structures that have an almost invariant system of O-HO hydrogen bonds. However, within this O-H…O framework, the four structures display variations that are characteristic of the C-H, C-F, C-Cl and C-Br groups. In the parent compound (1) aromatic rings are packed with a herringbone geometry, whilst in the halogenated derivatives (3) and (4), polarization-type halogenhalogen contacts are optimized. The fluoro derivative (2) is exceptional in that neither of the above possibilities is adopted, even though the O-H…O scaffolding does not per se prohibit either of them geometrically.γ-Hydroquinone (1) and its tetrafluoro, tetrachloro and tetrabromo derivatives (2), (3) and (4) adopt crystal structures that have an almost invariant system of O-HO hydrogen bonds. However, within this O-H…O framework, the four structures display variations that are characteristic of the C-H, C-F, C-Cl and C-Br groups. In the parent compound (1) aromatic rings are packed with a herringbone geometry, whilst in the halogenated derivatives (3) and (4), polarization-type halogenhalogen contacts are optimized. The fluoro derivative (2) is exceptional in that neither of the above possibilities is adopted, even though the O-H…O scaffolding does not per se prohibit either of them geometrically.

Item Type:Article
Source:Copyright of this article belongs to International Union of Crystallography.
Keywords:Hydroquinone; Comparative Study; Tetrahalogenated Derivatives; Hydrogen Bonding
ID Code:10910
Deposited On:09 Nov 2010 04:32
Last Modified:13 Jul 2012 10:19

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