SPECTRAL AND ELECTROOPTICAL PROPERTIES OF RING-SUBSTITUTED N-METHYL-N-PHENYLNITRAMINES

Citation
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
Citations number
33
Categorie Soggetti
Chemistry
Journal title
ISSN journal
01375083
Volume
69
Issue
10
Year of publication
1995
Pages
1437 - 1446
Database
ISI
SICI code
0137-5083(1995)69:10<1437:SAEPOR>2.0.ZU;2-9
Abstract
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.