Crystallography Journals Online : IUCR Backfile Archive 1948-2001
Chemistry and Pharmacology
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 C[triple-bond]C—H...O=C, Cmethylene—H...O(H) and Cmethyl—H...O(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.
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