Issue 22, 2014

Comparison of pyridyl and pyridyl N-oxide groups as acceptor in hydrogen bonding with carboxylic acid

Abstract

Competition experiments between pyridyl and pyridyl N-oxide groups have been performed to find out which of these two groups is a better acceptor in hydrogen bonding with the carboxylic acid group. 4,4′-bipyridine N-monoxide, a rigid, conjugated, and linear molecule and 4,4′-trimethylenebipyridine N-monoxide, a flexible, non-conjugated between two aryl groups, and bent molecule, have been used to synthesize complexes with some carboxylic acid containing compounds. The study shows that although the occurrence of pyridyl⋯acid synthon is more than the corresponding pyridyl N-oxide⋯acid synthon, based on the distance criterion and energy calculation, the pyridyl N-oxide⋯acid synthon is slightly stronger than the pyridyl⋯acid synthon. Solubility studies also show that the pyridyl N-oxide compound may be a better choice as a coformer than the corresponding pyridyl derivative to increase the solubility of carboxylic acid containing compounds.

Graphical abstract: Comparison of pyridyl and pyridyl N-oxide groups as acceptor in hydrogen bonding with carboxylic acid

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2013
Accepted
13 Jan 2014
First published
13 Jan 2014

CrystEngComm, 2014,16, 4715-4721

Author version available

Comparison of pyridyl and pyridyl N-oxide groups as acceptor in hydrogen bonding with carboxylic acid

V. G. Saraswatula, M. A. Bhat, P. K. Gurunathan and B. K. Saha, CrystEngComm, 2014, 16, 4715 DOI: 10.1039/C3CE42449A

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