NMR study of the conformation of N-(3-pyridinyl)-2- pyridinecarboxamide, N-(3-pyridinyl)acetamide and 2-pyridinecarboxamide

Anand, Jayashree and Singha, Netai C and Sathyanarayana, DN (1997) NMR study of the conformation of N-(3-pyridinyl)-2- pyridinecarboxamide, N-(3-pyridinyl)acetamide and 2-pyridinecarboxamide. In: Journal of Molecular Structure, 412 (3). pp. 221-229.

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Abstract

The $^IH$ NMR spectra of N-(3-pyridinyl)-2-pyridinecarboxamide (1), N-(3-pyridinyl)acetamide (2) and 2-pyridinecarbox- amide (3) in $CDCI_3$, $(CD_3)_2CO$ and $CD_3CN$ have been measured and analyzed by utilising the correlations in the COSY and HETCOR spectra, chemical shifts and coupling constants. $^1H$ NMR spectra in dilute solutions $(\sim1 mg \hspace {2mm}ml^{-1})$ and NOE experiments suggest (1) to occur in a single conformation with the 2-pyridyl ring coplanar with the amide plane and the 2-pyridyl nitrogen hydrogen bonded intramolecularly to the N-H. In concentrated solutions of $CDCl_3$ and $(CD_3)_2CO$, (1) dimerises by cooperative hydrogen bonding. The structure of the dimer was inferred to be similar to that of the adenine- adenine (A-A) base-pair.

Item Type:	Journal Article
Publication:	Journal of Molecular Structure
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Keywords:	NMR spectroscopy;Conformational isomerism;Hydrogen bonding;Pyridine carboxamides
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	22 Feb 2007
Last Modified:	19 Sep 2010 04:35
URI:	http://eprints.iisc.ac.in/id/eprint/10006

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