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Issue 3, 2001
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Competition between hydrogen bonding and donor–acceptor interactions in co-crystals of 1,3-dimethylbarbituric acid with aromatic amines

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Abstract

In contrast to cyclohexane-1,3-diones, 1,3-dimethylbarbituric acid (DMBA) does not enolize in crystals with formation of infinite H-bonded chains. Conversely, it forms crystals that completely lack traditional H-bond donors and hence are held together by C–H···O H-bonds and Cδ+[double bond, length half m-dash]Oδ−···Cδ+ interactions of a putative donor–acceptor nature. In view of these specific features, the DMBA molecule appeared to be a good candidate to study the competition of the various intermolecular forces in its co-crystals with traditional H-bond donors such as o-nitrophenylhydrazine, p-nitroaniline, 2,6-diamino-4-phenyl-1,3,5-triazine, 2,6-diaminopyridine and p-aminopyridine. X-Ray crystallographic results are analyzed in terms of crystal packing forces and formation of specific packing leitmotifs (supramolecular synthons). The conclusions indicate that, though a rational crystal engineering of co-crystals is far from being accomplished, a reasonable rationalization of the complex intermolecular forces acting in competition in the crystal packing is henceforth achievable.

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Publication details

The article was received on 12 Oct 2000, accepted on 23 Nov 2000 and first published on 15 Feb 2001


Article type: Paper
DOI: 10.1039/B008262G
Citation: New J. Chem., 2001,25, 408-415
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    Competition between hydrogen bonding and donor–acceptor interactions in co-crystals of 1,3-dimethylbarbituric acid with aromatic amines

    V. Bertolasi, P. Gilli, V. Ferretti and G. Gilli, New J. Chem., 2001, 25, 408
    DOI: 10.1039/B008262G

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