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NUCLEAR MAGNETIC RESONANCE AND X-RAY DIFFRACTION STUDIES ON SOME SUBSTITUTED BENZENESULPHONAMIDES

DOI: 10.1039/P29880000815

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 815 - 820 (1988)

Update date:2022-08-22

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Authors:

Haekkinen, Anna-MarijaHaekkinen, Anna-Marija

Ruostesuo, PirkoRuostesuo, Pirko

Kivekaes, RaikkoKivekaes, Raikko

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Article abstract of DOI:10.1039/P29880000815

Solid-state 13C c.p.-m.a.s. and solution 13C, 15N, and 17O n.m.r. spectra were measured for toluene-p-sulphonamide, N-methyltoluene-p-sulphonamide, NN-dimethyltoluene-p-sulphonamide, p-chlorobenzenesulphonamide, and NN-simethyl-p-chlorobenzenesulphonamide.The 13C c.p.-m.a.s. n.m.r. resonance lines of the carbon atoms bonded to nitrogen show characteristic line broadening with sligthly asymmetric doublet petterns.Some differences are evident in the 13C shielding of the carbon atoms between the solid-state and solution-state spectra.In the solution spectra the 15N and 17O chemical shifts increase in conformity with the polarity order of the amides.The n.m.r. relaxation times of the methyl groups of the compounds were measured as well.The crystal structures of N-methyltoluene-p-sulphonamide and NN-dimethyltoluene-p-sulphonamide were determined by single-crystal X-ray diffraction technique and refined to final R values of 0.056 and 0.044, respectively.Except for some baely significant differences, the bond lengths and angles are similar in the two compounds.The most striking difference is the value of the C-C-S-N torsion angle.

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