Products from Photochemical Reactions of Naphthalene in air

Bunce, Nigel J.; Zhu, Jiang

doi:10.1080/10406639408015163

Cited by 14 publications

(8 citation statements)

References 5 publications

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“…While some studies focus on homogeneous reactions between gas-phase parent PAHs and atmospheric oxidants, − others have focused on heterogeneous reactions between particle-phase parent PAHs and atmospheric radicals. ,,,, Data from the latter indicate that the products formed from heterogeneous reactions do not depend on the type of particle.…”

Section: Resultsmentioning

confidence: 99%

Evaluating Computational and Structural Approaches to Predict Transformation Products of Polycyclic Aromatic Hydrocarbons

Titaley

Walden

Dorn

et al. 2018

Environ. Sci. Technol.

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Polycyclic aromatic hydrocarbons (PAHs) undergo transformation reactions with atmospheric photochemical oxidants, such as hydroxyl radicals (OH•), nitrogen oxides (NOx), and ozone (O 3 ). The most common PAH-transformation products (PAH-TPs) are nitrated-, oxygenated-, and hydroxylated-PAHs (NPAHs, OPAHs, and OHPAHs, respectively), some of which are known to pose potential human health concerns. We sampled four theoretical approaches for predicting the location of reactive sites on PAHs (i.e., the carbon where atmospheric oxidants attack), and hence the chemoselectivity of the PAHs. All computed results are based on Density Functional Theory (B3LYP/6-31G(d) optimized structures and energies). The four approaches are: 1) Clar's prediction of aromatic resonance structures, 2) thermodynamic stability of all OHPAH adduct intermediates, 3) computed atomic charges (Natural Bond order, ChelpG, and Mulliken) at each carbon on the PAH, and 4) average local ionization energy (ALIE) at atom or bond sites. To evaluate the accuracy of these approaches, the predicted PAH-TPs were compared to published laboratory observations of major NPAH, OPAH, and OHPAH products in both gas-and particlephases. We found that the Clar's resonance structures were able to predict the least stable rings on the PAHs but did not offer insights in terms of which individual carbon is most reactive. The OHPAH adduct thermodynamics and the ALIE approaches were the most accurate when *

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Section: Resultsmentioning

confidence: 99%

Evaluating Computational and Structural Approaches to Predict Transformation Products of Polycyclic Aromatic Hydrocarbons

Titaley

Walden

Dorn

et al. 2018

Environ. Sci. Technol.

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“…It is well established that lipid peroxidation produces lipid alkoxy radicals and a number of tumorigenic aldehydes of low molecular weight, such as malondialdehyde, formaldehyde, crotonaldehyde, acrolein, 4-hydroxy-2-hexenal, and 4-hydroxy-2-nonenal. All of the low molecular weight aldehydes have been found to bind covalently with cellular DNA, form DNA adducts, and induce tumors in experimental animals [81][82][83][84][146][147][148]. Similar to ROS, lipid peroxidation is associated with many human diseases, including cancer, atherosclerosis, ischemia, inflammation, liver injury, aging, etc.…”

Section: Phototoxicity Of Pahs Oxygenated Pahs Pah Quinones Nimentioning

confidence: 98%

“…ROS can react with cellular constituents to generate reactive intermediates [81][82][83][84][146][147][148]. Both ROS and the reactive intermediates can damage cellular constituents such as cell membrane, nucleic acids, or proteins, causing DNA damage and inducing tumors in experimental animals.…”

Section: Phototoxicity Of Pahs Oxygenated Pahs Pah Quinones Nimentioning

confidence: 99%

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Xia

Sun

et al. 2012

Journal of Environmental Science and Health, Part C

196

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Polycyclic aromatic hydrocarbons (PAHs) are a class of mutagenic and tumorigenic environmental contaminants. Although the mechanisms by which PAHs induce cancer in experimental animals have been extensively studied and the metabolic activation pathways have been determined, the environmental fate of PAHs and the phototoxicity exerted by PAHs, as well as their photoreaction products formed in the environment, have received much less attention. In this review, the formation of oxygenated PAHs, PAH quinones, nitro-PAHs, and halogenated PAHs from photoreaction of environmental PAHs are addressed. Upon light irradiation, PAHs and all PAH photoreaction products can absorb light energy to reach photo-excited states, which react with molecular oxygen, medium, and coexisting chemicals to produce reactive oxygen species (ROS) and other reactive intermediates, such as oxygenated PAHs and free radicals. These intermediates, including ROS, induce lipid peroxidation, and DNA damage including DNA strand breakage, oxidation to 8-oxo-2'-deoxyguanosine, and DNA-adducts. Since these toxicological endpoints are associated with age-related diseases, including cancer, environmental PAHs concomitantly exposed to sunlight may potentially promote human skin damage, leading to ageing and skin cancers. Thus, we suggest that (i) in addition to the widely recognized metabolic pathways, more attention must be paid to photoreaction as an important activation pathway for PAHs, (ii) risk assessment of environmental PAHs should take into consideration the complex photochemical reactions leading to mixtures of products that are also phototoxic; and (iii) the study of structure-toxicity relationships should be expanded to cover the complex photoreactions and extrinsic factors that affect phototoxicity endpoints.

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“…This oxidative process is one of the chief degradation pathways for PAHs in the natural aquatic environment. Photodegradation products of the following PAHs are characterized: naphthalene in vapor (51)(52)(53), phenanthrene in silica-air inter-phase (54,55), anthracene in aqueous and organic solvents (56)(57)(58)(59)(60), pyrene in soil surface or on carbon (61-64), benzo[a]pyrene in aqueous media (65,66), and some heterocyclic compounds in solutions or on solid surfaces. Since then, characterization of photoproducts of some PAH in aqueous or water/organic solvent mixtures are available: naphthalene (53), pyrene (67,68), benz [a]anthracene (57,69,70), methyl substituted BAs (69), 1-hydroxypyrene (71), and 1-aminopyrene (AP).…”

Section: Pah Photochemistrymentioning

confidence: 99%

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

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Products from Photochemical Reactions of Naphthalene in air

Cited by 14 publications

References 5 publications

Evaluating Computational and Structural Approaches to Predict Transformation Products of Polycyclic Aromatic Hydrocarbons

Evaluating Computational and Structural Approaches to Predict Transformation Products of Polycyclic Aromatic Hydrocarbons

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

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