M. Mphahlele, Marole M. Maluleka
Apr 10, 2021
Citations
0
Influential Citations
1
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract One-pot sulfonyl chloride-pyridine mediated disulfonylation of the aniline nitrogen atom and dehydration of the primary amide group of the 5-halogenoanthranilamide derivatives afforded the corresponding N-(2-cyanophenyl)disulfonamides, exclusively. This facile reaction makes use of readily available substrates and gives high yield of the products in short reaction time. The structures of these compounds were characterised using a combination of nuclear magnetic resonance (1H NMR & 13C NMR), infrared (IR) and mass spectrometric techniques. Their geometry was distinctly confirmed by single crystal X-ray diffraction (XRD) analysis of N-(4-bromo-2-cyanophenyl)-N-(methylsulfonyl)methanesulfonamide (2a) as representative model. The geometrical optimizations of structures of compounds 2a, 2b and 2c were also investigated by means of density functional theory (DFT) calculations. The optimized structural parameters (bond lengths, bond angles, and torsion angles) of 2a have been compared with those of the X-ray structure.