7119-92-8Relevant articles and documents
Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide
Kuchurov,Fomenkov,Zlotin
experimental part, p. 2058 - 2062 (2011/01/08)
An efficient explosion-proof method was developed for the preparation of N,N-dialkylnitramines by treatment of dialkylammonium nitrates with a mixture of nitric acid and acetic anhydride in the presence of ZnCl2 in liduid or supercritical carbon dioxide.
Formation of N-nitrosamines and N-nitramines by the reaction of secondary amines peroxynitrite and other reactive nitrogen species: Comparison with nitrotyrosine formation
Masuda, Mitsuharu,Mower, Howard F.,Pignatelli, Brigitte,Celan, Irena,Friesen, Marlin D.,Nishino, Hoyoku,Ohshima, Hiroshi
, p. 301 - 308 (2007/10/03)
Reactive nitrogen species, including nitrogen oxides (N2O3 and N2O4), peroxynitrite (ONOO-), and nitryl chloride (NO2Cl), have been implicated as causes of inflammation and cancer. We studied reactions of secondary amines with peroxynitrite and found that both N-nitrosamines and N- nitramines were formed. Morpholine was more easily nitrosated by peroxynitrite at alkaline pH than at neutral pH, whereas its nitration by peroxynitrite was optimal at pH 8.5. The yield of nitrosomorpholine in this reaction was 3 times higher than that of nitromorpholine at alkaline pH, whereas 2 times more nitromorpholine than nitrosomorpholine was formed at pH 2N·), which react with nitric oxide (·NO) or nitrogen dioxide (·NO2) to yield nitroso and nitro secondary amines, respectively. Reaction of morpholine with NO· and superoxide anion (O2·-), which were concomitantly produced from spermine NONOate and by the xanthine oxidase systems, respectively, also yielded nitromorpholine, but its yield was 2·- inhibited its formation. Reactions of morpholine with nitrite plus HOCl or nitrite plus H2O2, with or without addition of myeloperoxidase or horseradish peroxidase, also yielded nitration and nitrosation products, in yields that depended on the reactants. Tyrosine was nitrated easily by synthetic peroxynitrite, by NaNO2 plus H2O2 with myeloperoxidase, and by NaNO2 plus H2O2 under acidic conditions. Nitrated secondary amines, e.g., N-nitroproline, could be identified as specific markers for endogenous nitration mediated by reactive nitrogen species.
N-Nitration of amides. VI. Mechanism of nitrolysis of N,N-dialkylamides of carboxylic acids by nitronium tetrafluoroborate in acetonitrile
Andreev, S. A.,Lebedev, B. A.,Tselinskii, I. V.,Shokhor, I. N.
, p. 1159 - 1166 (2007/10/02)
The kinetics of the nitrolysis of N,N-dialkylamides by nitronium tetrafluoroborate in an acetonitrile medium were investigated.The reaction rate is described by an equation of overall second order, i.e., first in the amide and first in the nitronium salt.The proposed mechanism for the nitrolysis of N,N-dialkylamides by nitronium tetrafluoroborate involves an equilibrium stage of the formation of a donor-acceptor complex betwen the nitronium salt and the amide (at the oxygen of the carbonyl group) in paralell with the irreversible nitrolysis stage.Nucleophilic assistance from the solvent has a significant effect on the kinetics of the nitrolysis of N,N-dialkylamides.
N-Nitration of amides. VII. Kinetics of the nitrolysis of N,N-dialkylamides of carboxylic acids by nitronium tetrafluoroborate in acetonitrile
Andreev, S. A.,Lebedev, B. A.,Tselinskii, I. V.
, p. 1166 - 1170 (2007/10/02)
The kinetics of the nitrolysis of amides R2NC(O)R', where R=C2H5, R'=tert-C4H9, iso-C4H9, C4H9, iso-C3H7, C3H7, CH3, CH2Cl, CH2CN, CCl3; R'=CH3, R=CH3, C3H7, C4H9, by nitronium tetrafluoroborate in an acetonitrile medium were investigated.It was established that the polar effect of the substituents in the acyl group of the amides (R') shows up mostly in the overallrate of the process.The effect of substituents at the nitrogen atom (R) is due to the steric effects of the alkyl groups.
