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Probing acid-amide intermolecular hydrogen bonding by NMR spectroscopy and DFT calculations

Chaudhari, Sachin Rama and Suryaprakash, N (2012) Probing acid-amide intermolecular hydrogen bonding by NMR spectroscopy and DFT calculations. In: JOURNAL OF MOLECULAR STRUCTURE, 1016 . pp. 163-168.

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Official URL: http://dx.doi.org/10.1016/j.molstruc.2012.02.058


Benzene carboxylic acids and Benzamide act as their self-complement in molecular recognition to form inter-molecular hydrogen bonded dimers between amide and carboxylic acid groups, which have been investigated by H-1, C-13 and N-15 NMR spectroscopy. Extensive NMR studies using diffusion ordered spectroscopy (DOSY), variable temperature 1D, 2D NMR, established the formation of heterodimers of benzamide with benzoic acid, salicylic acid and phenyl acetic acid in deuterated chloroform solution. Association constants for the complex formation in the solution state have been determined. The results are ascertained by X-ray diffraction in the solid state. Intermolecular interactions in solution and in solid state were found to be similar. The structural parameters obtained by X-ray diffraction studies are compared with those obtained by DFT calculations. (C) 2012 Elsevier B.V. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elsevier
Keywords: Intermolecular hydrogen bonds;NMR spectroscopy;Diffusion ordered spectroscopy (DOSY);DFT;Benzamide;Benzene carboxylic acids
Department/Centre: Division of Chemical Sciences > NMR Research Centre (Formerly Sophisticated Instruments Facility)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 27 Jun 2012 07:55
Last Modified: 27 Jun 2012 07:55
URI: http://eprints.iisc.ac.in/id/eprint/44739

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