22904-44-5Relevant articles and documents
Homogenous Gas-Phase Formation and Destruction of Anthranil from o-Nitrotoluene Decomposition
He, Y. Z.,Cui, J. P.,Mallard, W. G.,Tsang, W.
, p. 3754 - 3759 (1988)
Dilute quantities of o-nitrotoluene and anthranil have been pyrolyzed in comparative rate single pulse shock tube experiments.Rather than C-NO2 bond cleavage and NO2 isomerization found as major channels in p-nitrotoluene decomposition, we demonstrate that the important pathway for pyrolysis involves the formation of anthranil with the following overall rate expression: k(o-nitrotoluene -> anthranil) = 1.2 x 1013 exp(-26020/T)/s.The anthranil that is formed is very unstable under our conditions; the rate expression for disappearence has been found to be the following: k(anthranil)d = 3.7 x 1015 exp(-25800/T)/s.Arguments are presented that suggest that the first rate expression is representative of a retroene reaction and the second expression is for the breaking of the N-O bond in anthranil.These conclusions emphasize the difference in results from shock tube and laser pyrolysis experiments.Their implications on the initiation reactions in the decomposition of nitroaromatic explosives are discussed.
Investigating the mechanisms of aromatic amine-induced protein free radical formation by quantitative structure-activity relationships: Implications for drug-induced agranulocytosis
Siraki, Arno G.,Jiang, Jinjie,Mason, Ronald P.
experimental part, p. 880 - 887 (2011/03/17)
Aromatic amine drugs have been associated with agranulocytosis (neutrophil depletion) for which the mechanism is unknown. We have previously shown that the metabolism of two aromatic amine drugs by human myeloperoxidase (MPO) results in phenyl radical metabolite formation and also in protein free radical formation on MPO. Because the concentration of drug required to produce a maximum signal for MPO protein free radical (MPO?) detection was different for each drug, this prompted us to consider that other aromatic amines may also show varying degrees of ability to induce MPO? formation. Immunoassay experiments using the immuno-spin-trapping technique were performed, which evaluated the potency of different aromatic amines containing the aniline substructure to generate the MPO?. Each reaction contained equal amounts of H2O2, 5,5-dimethyl-1-pyrroline- N-oxide, MPO, and variable concentrations of aniline derivatives. Several physicochemical parameters for aniline derivatives were used to derive quantitative structure-activity relationship equations, which showed that the Hammett constant (-) best correlated with the MPO? formation for all aniline derivatives. More statistically robust equations were derived if the anilines were separated into mono- and disubstituted groups. However, some aniline derivatives did not induce MPO? formation. Using electron spin resonance spectroscopy, we evaluated the ability of all aniline derivatives tested to produce phenyl radical metabolites, as previously shown by spin trapping for the aromatic amine drugs. Interestingly, we found that only those aniline derivatives that produced a phenyl radical also formed MPO ?. We propose that the phenyl radical is the reactive free radical metabolite responsible for generating the MPO?+.
