Singh, Netai C and Sathyanarayana, DN (1998) 1H and 13C NMR spectral studies of conformation of some N-(2-pyridinyl)-3-pyridinecarboxamides. In: Journal of Molecular Structure, 449 (1). pp. 91-98.
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Abstract
The 1H and 13C NMR spectra of N-(2-pyridinyl)-, N-(4-methyl2-pyridinyl)-, and N-(6-methyl-2-pyridinyl)-3-pyridine-carboxamides (1�3, respectively) and 3-pyridinecarboxamide (4) in different solvents have been analysed using COSY, HETCOR, chemical shift and coupling constant correlations. The conformations of 1�4 have been obtained by utilizing the NMR spectra, NOE experiments and MINDO/3 calculations. In dilute solutions, the 2-pyridyl ring is coplanar with the amide group while the 3-pyridyl ring is apparently not. Compounds 1�3 dimerize through cooperative hydrogen bonding in concentrated CDCl3 solution (approximately 0.1 M) and the structure of the dimer resembles some of the DNA base-pairs. Hydrogen bonding between N---H and the solvent molecules hinders dimerization in (CD3)2CO and CD3CN.
Item Type: | Journal Article |
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Publication: | Journal of Molecular Structure |
Publisher: | Elsevier science |
Additional Information: | Copyright of this article belongs to Elsevier science. |
Keywords: | NMR spectroscopy;Molecular conformation;Hydrogen bonding; Association;Pyridinecarboxamides. |
Department/Centre: | Division of Chemical Sciences > Inorganic & Physical Chemistry |
Date Deposited: | 09 Jun 2011 07:19 |
Last Modified: | 09 Jun 2011 07:19 |
URI: | http://eprints.iisc.ac.in/id/eprint/38114 |
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