13177-28-1Relevant articles and documents
Formation of mutagenic nitrofluoranthenes in the gas-solid heterogeneous reaction of particle-associated fluoranthene in NO2-O3-O2 system
Inazu, Koji,Kobayashi, Takaaki,Hisamatsu, Yoshiharu
, p. 1105 - 1106 (1996)
In the gas-solid heterogeneous reactions of particle-supported fluoranthene with ppm levels of nitrogen dioxide and ozone, dinitrofluoranthenes and 3-introfluoranthene (3-NF) were formed only in the dark and 2-NF was formed only under photoirradiation while 1-, 7-, and 8-NFs were formed under both conditions. Yield and distribution of the products varied depending on the kind of supports employed.
A dichotomy in the nitration of fluoranthene with NO2/N2O4: Mechanistic and toxicological implications
Squadrito,Fronczek,Church,Pryor
, p. 2616 - 2621 (2007/10/02)
The nitration of fluoranthene with nitrogen dioxide can occur by two distinctive reaction pathways. These paths can be distinguished by product analysis, since fluoranthene is a nonalternant hydrocarbon. Free-radical nitration and electrophilic nitration give different products. In solvents with dielectric constants lower than that of CH2Cl2 and in the absence of acid catalysis, the exclusive reaction pathway is homolytic in nature. The products of the homolytic reaction pathway can be interpreted as arising via a multiple-step addition-elimination mechanism and are notable for the formation of 2-nitrofluoranthene (the major product in CCl4 but absent under electrophilic nitration conditions) and the unusually large amounts of the expected 1,2-dinitrofluoranthene and 1,3-dinitrofluoranthene. The ionic reaction pathway is subject to both Lewis and Bronsted acid catalysis, particularly in CH2Cl2, and is inhibited by nonnucleophilic bases like 2, 6-di-tert-butylpyridine. At temperatures lower than 25°C, the ionic reaction pathway predominates, even in CCl4. 2-Nitrofluoranthene is a marker for the free-radical nitration of fluoranthene, and its presence in polluted tropospheric air suggests that free-radical nitration by NO2 may occur under atmospheric conditions.
Reaction of Dinitrogen Pentoxide with Fluoranthene
Zielinska, Barbara,Arey, Janet,Atkinson, Roger,Ramdahl, Thomas,Winer, Arthur M.,Pitts, James N. Jr.
, p. 4126 - 4132 (2007/10/02)
The products and mechanisms of the reactions of dinitrogen pentoxide (N2O5) with fluoranthene (FL) in aprotic solvents have been investigated.The influence of solvent polarity and temperature and the effects of addition of HNO3 on the resulting nitrofluoranthene (NFL) isomer distributions have been studied.These data compared with the NFL isomer distributions resulting from the reactions of FL with N2O5 and other nitrating agents in the gas and absorbed phases.In the gas phase and in CCl4 solution at ambient temperature, 2-NFL is the only mononitro isomer formed from the reaction of FL with N2O5.However, in more polar solvents (CH3CN and CH3NO2) and in CCl4 at subambient remperature (-15 grad C), as well as with FL in the adsorbed state, reaction with N2O5 produces only the 3-, 8-, 7-, and 1-NFL isomers.A homolyticmechanism for the formation of the 2-NFL isomer is postulated.