Hydrogen-bonding in the structures of the 1:1 salts of isonipecotamide with a set of four polyfunctional monocyclic heteroaromatic carboxylic acids
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2012
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Resumo |
The crystal structures of the 1:1 proton-transfer compounds of isonipecotamide (piperidine-4-carboxamide) with the monocyclic heteroaromatic carboxylic acids, isonicotinic acid, picolinic acid, dipicolinic acid and pyrazine-2,3-dicarboxylic acid have been determined at 200 K and their hydrogen-bonding patterns examined. The compounds are respectively anhydrous 4-carbamoylpiperidinium pyridine-4-carboxylate (1), the partial hydrate 4-carbamoylpiperidinium pyridine-2-carboxylate 0.25 water (2), the solvate 4-carbamoylpiperidinium 6-carboxypyridine-2-carboxylate methanol monosolvate (3), and anhydrous 4-carbamoylpiperidinium 3-carboxypyrazine-2-carboxylate (4). In compounds 1 and 3, hydrogen-bonding interactions give two-dimensional sheet structures which feature enlarged cyclic ring systems, while in compounds 2 and 4, three-dimensional structures are found. The previously described cyclic R2/2(8) hydrogen-bonded amide-amide dimer is present in 2 and 3. The hydrogen-bonding in 2 involves the partial-occupancy water molecule while the structure of 4 is based on inter-linked homomolecular hydrogen-bonded cation-cation and anion-anion associated chains comprising head-to-tail interactions. This work further demonstrates the utility of the isonipecotamide cation in the generation of chemically stable hydrogen-bonded systems, particularly with aromatic carboxylate anions, providing crystalline solids. |
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application/pdf |
Identificador | |
Publicador |
Oldenbourg Wissenschaftsverlag GmbH |
Relação |
http://eprints.qut.edu.au/53791/2/53791.pdf DOI:10.1524/zkri.2012.1543 Smith, Graham & Wermuth, Urs (2012) Hydrogen-bonding in the structures of the 1:1 salts of isonipecotamide with a set of four polyfunctional monocyclic heteroaromatic carboxylic acids. Zeitschrift fuer Kristallographie, 227(9), 656-664 . |
Direitos |
Copyright 2012 Oldenbourg Wissenschaftsverlag GmbH |
Fonte |
School of Chemistry, Physics & Mechanical Engineering; Science & Engineering Faculty |
Palavras-Chave | #030000 CHEMICAL SCIENCE #crystal structure #isonipecotamide #hydrogen bonding |
Tipo |
Journal Article |