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Issue 11, 2002
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Hydrogen-bonded supramolecular structures in co-crystals of β- or ζ-diketone enols with 2,6-diaminopyridine or 2,4-diaminopyrimidine

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Abstract

Preparation and single-crystal X-ray structure determination of five co-crystals of conjugated β- or ζ-diketoenolate anions (1,3-cyclopentanedionate, 1,3-cyclohexanedionate, 5-methyl-1,3-cyclohexanedionate and tropolonate) with aromatic protonated nitrogen bases (2,6-diaminopyridinium and 2,4-diaminopyrimidinium) are reported. Their packings are discussed in terms of the relative energies of the intermolecular hydrogen bonds formed, calculated by the Lippincott and Schroeder method, showing that such bonds largely determine the supramolecular net of interconnections within the crystal. The β- and ζ-diketoenolate anions are shown to have specific properties, being π-conjugated fragments with two terminal oxygens sharing a single negative charge that is partially displaced on one side or another according to the strength of the hydrogen bonds formed. The β-cyclohexanedionate anion displays, moreover, the ability to form a dimeric association with its neutral form through a very strong central [O–H⋯O] bond of charge-assisted nature.

Graphical abstract: Hydrogen-bonded supramolecular structures in co-crystals of β- or ζ-diketone enols with 2,6-diaminopyridine or 2,4-diaminopyrimidine

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Article information


Submitted
11 Jun 2002
Accepted
01 Aug 2002
First published
17 Oct 2002

New J. Chem., 2002,26, 1559-1566
Article type
Paper

Hydrogen-bonded supramolecular structures in co-crystals of β- or ζ-diketone enols with 2,6-diaminopyridine or 2,4-diaminopyrimidine

V. Bertolasi, L. Pretto, P. Gilli, V. Ferretti and G. Gilli, New J. Chem., 2002, 26, 1559
DOI: 10.1039/B205705K

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