4-ethynyl-4-hydroxycyclohexan-1-one and 4-ethynyl-4-hydroxy-2,3,5,6-tetramethylcyclohexa-2,5-dien-1-one

Bilton, C. ; Howard, J. A. K. ; Madhavi, N. N. L. ; Desiraju, G. R. ; Allen, F. H. (2000) 4-ethynyl-4-hydroxycyclohexan-1-one and 4-ethynyl-4-hydroxy-2,3,5,6-tetramethylcyclohexa-2,5-dien-1-one Acta Crystallographica Section C: Crystal Structure Communications, 56 . pp. 1356-1358. ISSN 0108-2701

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Official URL: http://scripts.iucr.org/cgi-bin/paper?gd1109

Related URL: http://dx.doi.org/10.1107/S0108270100011355


The title compounds, C8H10O2, (I), and C12H14O2, (II), occurred as by-products in the controlled synthesis of a series of bis(gem-alkynols), prepared as part of an extensive study of synthon formation in simple gem-alkynol derivatives. The two 4-(gem-alkynol)-1-ones crystallize in space group P21/c, (I) with Z' = 1 and (II) with Z' = 2. Both structures are dominated by O-H …O=C hydrogen bonds, which form simple chains in the cyclohexane derivative, (I), and centrosymmetric dimers, of both symmetry-independent molecules, in the cyclohexa-2,5-diene, (II). These strong synthons are further stabilized by CC-H …O=C, Cmethylene-H …O(H) and Cmethyl-HO(H) interactions. The direct intermolecular interactions between donors and acceptors in the gem-alkynol group, which characterize the bis(gem-alkynol) analogues of (I) and (II), are not present in the ketone derivatives studied here.

Item Type:Article
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ID Code:10914
Deposited On:09 Nov 2010 04:31
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