Search results for "amphiprotic compounds"

Acidity and basicity of primaryN-phenylnitramines: catalytic effect of protons on the nitramine rearrangement

2002

Para-substituted N-phenylnitramines were prepared either by oxidation of diazonium salts or by nitration under alkaline or acidic conditions. Isotopic [15N-NO2] labelling indicated that the bands characteristic of the N-nitro group appear in the 1318–1323 and 1585–1607 cm−1 regions. In the nitrogen NMR spectra, the nitramino group gives two resonances at −193 ± 3 (NH) and −32 ± 3 ppm (NO2). The chemical shifts in proton and carbon NMR spectra are predictable, based on increments and the additivity rule. The spectral data indicate the lack of conjugation between the nitramino group and another substituent bound to the ring. It seems to contradict the well-known fact that substituents strongl…