Hydrogen-bonding in the structures of the 1:1 salts of isonipecotamide with a set of four polyfunctional monocyclic heteroaromatic carboxylic acids

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 .

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Abstract

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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ID Code: 53791
Item Type: Journal Article
Refereed: Yes
Keywords: crystal structure, isonipecotamide, hydrogen bonding
DOI: 10.1524/zkri.2012.1543
ISSN: 0044-2968
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2012 Oldenbourg Wissenschaftsverlag GmbH
Deposited On: 23 Sep 2012 23:57
Last Modified: 23 Mar 2013 10:52

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