ISSN:
0749-1581
Keywords:
Sulphonamide
;
Sulphinamide
;
Multinuclear NMR
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
13C, 15N and 17O NMR chemical shifts, and also 1J(CH) and 1J(NH) values, have been determined for variously substituted sulphonamides and some sulphinamides, either neat or in acetone or dimethyl sulphoxide solution.The effect of benzene ring substituents on the chemical shifts of nitrogen and oxygen nuclei is slight, but N-substitution changes the shielding of both nuclei. Generally, an N-methyl substituent shields an amide nitrogen and an N,N-dimethyl substituent gives further slight shielding. On the other hand, an N-phenyl substituent deshields the nitrogen strongly, but the deshielding effect of an N,N-diphenyl substituent is markedly smaller. The sulphonyl oxygens are deshielded relative to the sulphinyl oxygens, and N-methyl and N,N-dimethyl substituents shield the oxygen nucleus. The effect of N-phenyl and N,N-diphenyl substituents on the shielding of the oxygen atoms of the sulphonyl group is slight.The direct 1J(CH) coupling constants are similar, but they are characteristic of different type of sulphur amides. The 1J(NH) values are of the same order of magnitude for sulphonamides and sulphinamides, but are clearly smaller for N-unsubstituted amides than for N-substituted compounds.
Additional Material:
8 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260250302
