19092-03-6Relevant articles and documents
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.
Photolysis of some N-nitroso- and N-nitro-anilines in solution
Gowenlock, Brian G.,Pfab, Josef,Young, Victor M.
, p. 915 - 919 (2007/10/03)
The photolyses of three N-methyl-N-nitrosoanilines and two N-methyl-N-nitroanilines in organic solvents have been studied in the range of 300-340 nm. The influence of solvent character and the presence or absence of oxygen play important roles in the product composition range. The primary photochemical process involves N-N fission, this being homolytic in aprotic solvents and heterolytic in methanol. Three novel mechanistic conclusions are proposed, namely photosolvolysis of a nitrosamine in methanol, photooxidation of nitrosamines in aprotic solvents and the production of biphenyl derivatives on photolysis of nitro-substituted nitrosamines and nitramines in aromatic solvents.
