Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives
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- 作者：Paul W. Baures ; Jeremy R. Rush ; Alexander V. Wiznycia ; John Desper ; Brian A. Helfrich ; and Alicia M. Beatty
- 刊名：Crystal Growth & Design
- 出版年：2002
- 出版时间：November 2002
- 年：2002
- 卷：2
- 期：6
- 页码：653 - 664
- 全文大小：433K
- 年卷期：v.2,no.6(November 2002)
- ISSN：1528-7505
文摘
Diamide and amide-ester derivatives of imidazole-4,5-dicarboxylic acid form reliable hydrogen-bondingmotifs in the solid state. The crystal structures of symmetrically substituted and dissymmetrically substituteddiamides as well as amide-ester combinations were analyzed in order to identify the intermolecular hydrogen-bondingpatterns. An intramolecular seven-membered hydrogen-bonded conformation forms in all derivatives where thepossibility existed due to the functionality present. The motifs observed for the diamides include intermolecularNH···O and NH···N hydrogen-bonded dimers, with the exceptions to these motifs occurring in compounds havingbenzylamine substituents. The amines with a higher classification (i.e., 3
> 2 > 1) in the dissymmetricallysubstituted diamides are the intramolecular hydrogen bond donors in the solid state, consistent with the capacityof the alkyl group to stabilize developing carbocation character resulting from bond polarization. The amide-esterderivatives also form an intramolecular hydrogen bond and an intermolecular motif based on NH···N and two differentC2-H···O hydrogen bonds. A pyrrole amide-ester derivative forms an intramolecular NH···O hydrogen bond in thesolid state and an intermolecular NH···O hydrogen-bonded chain. With the exception of the benzylamine-substituteddiamides, the intermolecular hydrogen-bonded motifs appear reliable for these imidazole-4,5-dicarboxylic acidderivatives and will be useful in the design of analogues for specific applications.
> 2 > 1) in the dissymmetricallysubstituted diamides are the intramolecular hydrogen bond donors in the solid state, consistent with the capacityof the alkyl group to stabilize developing carbocation character resulting from bond polarization. The amide-esterderivatives also form an intramolecular hydrogen bond and an intermolecular motif based on NH···N and two differentC2-H···O hydrogen bonds. A pyrrole amide-ester derivative forms an intramolecular NH···O hydrogen bond in thesolid state and an intermolecular NH···O hydrogen-bonded chain. With the exception of the benzylamine-substituteddiamides, the intermolecular hydrogen-bonded motifs appear reliable for these imidazole-4,5-dicarboxylic acidderivatives and will be useful in the design of analogues for specific applications.