Syntheses and Some Properties of N-Alkyldimethylaminealkanesulfonimides

Abstract

N- Trimethylaminealkanesulfonimides (1-R-S) and N-alkyl-dimethylaminemethanesulfonimides (R-1-S), R : n-C12H25 and n-C16H33, were derived from 1, 1-dimethyl- or 1-alkyl-1-methyl-hydrazine. Their properties were compared with those of the corresponding amineimides, (1-R) and (R-2).On NMR spectra of the ylides, the chemical shift for methyl or methylene groups adjacent to the positive nitrogen was 3.4ppm relative to TMS. For amineimides, it was 3.203.29ppm. On IR spectra, S-O frequencies of the aminesulfonimides were lowered by 60100cm-1 in comparison with those of the corresponding hydrazines or hydrazinium salts. This frequency fall is probably due to a delocalization of the negative charge on the nitrogen, similar to that operating in amineimides. But the degree of this fall was larger than that for amineimides.The aqueous solution was neutral and showed a low electric conductivity, analogous to those of amineimides. The comparison of their properties among the four types of ylides having the same alkyl groups gave the following results : mp, 1-R-S>R-1-S>1-R>R-2; Krafft point, R-1-S>1-R-S>1-R>R-2; cmc, 1-R-S<R-1-S<R-2<1-R; surface tension above cmc, R-1-S<1-R-S<1-R<R-2. Foaming and penetrating powers were also measured.