Z. Daszkiewicz et al., SPECTRAL AND ELECTROOPTICAL PROPERTIES OF RING-SUBSTITUTED N-METHYL-N-PHENYLNITRAMINES, Polish Journal of Chemistry, 69(10), 1995, pp. 1437-1446
Secondary aromatic nitramines absorb in IR at 1517-1536, 1285-1299 and
755-759 cm(-1) irrespective of the nature of an aromatic ring. Compar
ison of the H-1 and C-13 NMR spectra of ring substituted N-methyl-N-ph
enylnitramines indicate that interaction between the substituents is p
oorly transmitted across the ring. alpha-Cleavage observed in the mass
spectra of nitramines shows that the Ar-N bond is abnormally weak. Di
pole moments of N-methyl-N-phenylnitramines find a simple explanation
assuming that the unshared electron pair is shifted towards the aromat
ic ring only in the presence of electron demanding substituents in con
jugated position. The results are incompatible with the solvent-caged-
pair theory of the nitramine rearrangement.