Nitration of Polycyclic Aromatic Hydrocarbons with Dinitrogen Tetroxide. A Simple and Selective Synthesis of Mononitro Derivatives.

Radner, Finn; Laitalainen, Tarja; Mosihuzzaman, M.; Johnels, Dan; Hellberg, Sven; Sjöstróm, Michael; Wold, Svante; Mahedevan, Ramanathan

doi:10.3891/acta.chem.scand.37b-0065

Cited by 39 publications

(17 citation statements)

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“…Gas-phase formation of nitro-PAHs via OH or NO 3 radicalinitiated reaction involves the addition of an OH or NO 3 radical to PAH at the carbon atom with the highest electron density, followed by ortho-addition of NO 2 , resulting in loss of water or nitric acid. For triphenylene, the carbon at the 1-position is the most electron-rich; 20,21) therefore, preferential formation of 2-NTP over 1-NTP is expected in the gas-phase The rate constants of gas-phase reactions of triphenylene with OH and NO 3 radicals at 298 K were predicted to be (8.6 ± 1.2) × 10 −12 cm 3 molecule −1 s −1 and (6.6 ± 1.5) × 10 −29 [NO 2 ] cm 3 molecule −1 s −1 , respectively using a relativerate method in a CCl 4 liquid phase-system. 22) Based on the ambient concentration of 2-NTP and the obtained rate constant for the reaction of triphenylene with the radicals, the atmospheric loss rate of 2-NTP relative to 2-NFR, which is the most abundant NPAH and is also produced from the radical reactions, was successfully estimated, i.e.…”

Section: Formation Of Nitrotriphenylenes By Radical-initiated Reactionsmentioning

confidence: 99%

Atmospheric Chemistry of Polycyclic Aromatic Hydrocarbons and Related Compounds

Kameda

2011

JOURNAL OF HEALTH SCIENCE

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Polycyclic aromatic compounds are ubiquitous atmospheric pollutants with toxic, mutagenic, and carcinogenic properties. They are produced from chemical reactions of their parent compounds in the atmosphere as well as from a wide variety of anthropogenic sources such as fuel combustions. The present review is mainly concerned with several reaction pathways regarding secondary formation of atmospheric polycyclic aromatic hydrocarbon (PAH) derivatives, i.e., formation of mutagenic nitrated PAHs, 1-and 2-nitrotriphenylene, via gas-phase OH or NO 3 radical-initiated reactions of the parent triphenylene, atmospheric formation of hydroxynitropyrenes from a photochemical reaction of 1-nitropyrene, and photochemical degradation of selected nitrated and oxygenated PAHs on airborne particles under simulated solar UV-irradiation.

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Section: Formation Of Nitrotriphenylenes By Radical-initiated Reactionsmentioning

confidence: 99%

Atmospheric Chemistry of Polycyclic Aromatic Hydrocarbons and Related Compounds

Kameda

2011

JOURNAL OF HEALTH SCIENCE

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“…The photoinduced degradation of benzo[a]anthracene is accelerated in the presence of quinones (9,10-anthraquinone, 9,10phenanthrenequinone) and carbonylic compounds (xanthone, 2-furaldehyde, 2,4dimethylbenzaldehyde, 2-acetylfuran), 49 which are known constituents of atmospheric particulate and aerosols. [58][59][60][61] Nitration by HNO 3 takes place via an electrophilic mechanism involving NO 2 + : These oxides have either crustal origin 50 or originate from the corrosion of car engines and in this case are associated with carbonaceous particulate.…”

Section: Processes That May Occur In the Condensed Phasementioning

confidence: 99%

Polycyclic Aromatic Hydrocarbons in the Atmosphere: Monitoring, Sources, Sinks and Fate. II: Sinks and Fate

et al. 2004

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This paper reviews the transformation processes that polycyclic aromatic hydrocarbons (PAHs) undergo in the atmosphere. These processes can take place both in the gas phase and in the particulate/aerosol one. Among the gas-phase processes, the most important ones are the daytime reaction with *OH and the nighttime reaction with *NO3. The relative importance of the two processes depends on the particular PAH molecule. For instance, gaseous naphthalene is mainly removed from the atmosphere upon reaction with *OH, while gaseous phenanthrene is mainly removed by reaction with *NO3. Oxy-, hydroxy-, and nitro-PAHs are the main transformation intermediates. Reaction with ozone and photolysis play a secondary role in the transformation of gaseous PAHs. The particle-associated processes are usually slower than the gas-phase ones, thus the gas-phase PAHs usually have shorter atmospheric lifetimes than those found on particulate. Due to the higher residence time on particulate when compared with the gas phase, direct or assisted photolysis plays a relevant role in the transformation of particle-associated PAHs. Among the other processes taking place in the condensed phase, nitration plays a very important role due to the health impact of nitro-PAHs, some of them being the most powerful mutagens found so far in atmospheric particulate extracts.

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“…25 Smectic column (liquid crystalline polysiloxane, film thickness 0.15 pm, Lee Scientific). Helium was used as carrier gas in all cases.…”

Section: Gas Chromatographymentioning

confidence: 99%