102877-65-6Relevant articles and documents
N-Methyl-N-(2-nitrophenyl)nitramine and N-methyl-N-(3-nitrophenyl)- nitramine
Zarychta, Bartosz,Piecyk-Mizgala, Anna,Daszkiewicz, Zdzislaw,Zaleski, Jacek
, p. o515-o517 (2005)
The structures of the two title isomeric compounds (systematic names: N-methyl-N,2-dinitroaniline and N-methyl-N,3-dinitroaniline, both C 7H7N3O4) are slightly different because they exhibit different steric hindrances and hydrogen-bonding environments. The aromatic rings are planar. The -N(Me)NO2 and -NO2 groups are not coplanar with the rings. Comparison of the geometric parameters of the ortho, meta and para isomers together with those of N-methyl-N-phenylnitramine suggests that the position of the nitro group has a strong influence on the aromatic ring distortion. The crystal packing is stabilized by weak C-H...O hydrogen bonds to the nitramine group.
Synthesis, properties, and molecular structure of nitro-substituted N-methyl-N-nitroanilines
Prezhdo,Bykova,Prezhdo,Daszkiewicz,Kyziol,Zaleski
, p. 64 - 75 (2007/10/03)
Ten mono-, di-, and trinitro derivatives of N-methyl-N-nitroaniline were synthesized and studied by spectral, electrooptical, and quantum-chemical methods. Three of these derivatives, N-methyl-N,2,3-trinitroaniline, N-methyl-N,2,5-trinitroaniline, N-methyl-N,3,5-trinitroaniline, were also examined by the X-ray diffraction method. The N-nitroamino group in their molecules is almost planar, the N7-N8 bond is shortened, and the N8 atom is characterized by a strong deficit of electron density. The dihedral angle between the planes of the N-nitroamino group and the benzene ring is 56°-92°, which makes conjugation between these fragments impossible. The N-nitroamino group in the examined compounds acts as a weak electron donor with respect to the nitro groups in the aromatic ring; the mechanism of this effect is inductive. Pleiades Publishing, Inc. 2006.
Synthesis and properties of secondary N-nitroamines
Prezhdo,Daszkiewicz,Kyziol,Bykova,Prezhdo
, p. 410 - 416 (2007/10/03)
Secondary arylamines and related compounds can readily be converted into the corresponding N-nitroamines by treatment of their organomagnesium derivatives with butyl nitrate. The yield of the products ranges from 45 to 77%. Secondary aromatic N-nitroamine
Structure and properties of some nitro derivatives of N-methyl-N-phenylnitramine
Daszkiewicz,Kyziol,Predo,Zaleski
, p. 9 - 18 (2007/10/03)
Ten mono-, di- and tri-nitro derivatives of N-methyl-N-phenylnitramine were prepared and investigated using spectral and electrooptical methods. Three of them, viz. N-(2, 5-dinitrophenyl)-N-methylnitramine (monoclinic, P21/c, a = 8.248(2), b = 11.655(2), c = 10.404(2) ?, β = 102.57(2)°), N-(2,3-dinitrophenyl)-N-methylnitramine (monoclinic, P21/c, a = 9.224(2), b = 7.222(2), c = 15.458(4) ?, β = 101.08(2)°)) and N-(3,5-dinitrophenyl)-N-methylnitramine (monoclinic, P21/n, a = 9.814(2), b = 12.000(2), c = 8.865(2) ?, β = 114.94(2)°) were examined by the X-ray diffraction method. The nitramino group is nearly planar with the short N(7)-N(8) bond and strongly electron deficient N(8) atom. The nitramino group is twisted vs. the aromatic ring, there is no conjugation between the nitro and nitramino groups across the ring. The nitramino group is an electron withdrawing substituent due to the inductive effect. The number and positions of the At-nitro groups have no influence on the N-nitro group. Its migration ability cannot be explained in terms of the interaction between the migration origin and the ring substituents. (C) 2000 Elsevier Science B.V.
