Amide-to-Amide Hydrogen Bonds in the Presence of a Pyridine Functionality:  Crystal Structures of Bis(pyridinecarboxamido)alkanes

Crystal structures of bis(4-pyridinecarboxamido)alkane and bis(3-pyridinecarboxamido)alkane derivatives were determined and analyzed in terms of hydrogen bond networks. Seven crystal structures out of the eight structures studied exhibited amide-to-amide hydrogen bonds. Out of these seven, five form...

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Bibliographic Details
Published in:Crystal growth & design 2006-01, Vol.6 (1), p.202-208
Main Authors: Sarkar, Madhushree, Biradha, Kumar
Format: Article
Language:English
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Summary:Crystal structures of bis(4-pyridinecarboxamido)alkane and bis(3-pyridinecarboxamido)alkane derivatives were determined and analyzed in terms of hydrogen bond networks. Seven crystal structures out of the eight structures studied exhibited amide-to-amide hydrogen bonds. Out of these seven, five form the anticipated β-sheet network whereas two structures form a doubly interpenetrated (4,4)-network. In only one structure does the pyridyl group interfere in the amide-to-amide hydrogen bond, leading to the formation of an N−H···N hydrogen bond network. The analyses and rationalization of these structures and also related derivatives in the Cambridge Structural Database suggested that amide-to-amide hydrogen bond formation depends on the interplanar angle between amide and pyridine groups.
ISSN:1528-7483
1528-7505
DOI:10.1021/cg050292l