Formation Mechanism of Benzo(a)pyrene: One of the Most Carcinogenic Polycyclic Aromatic Hydrocarbons (PAH)

The formation of polycyclic aromatic hydrocarbons (PAHs) is a strong global concern due to their harmful effects. To help the reduction of their emissions, a crucial understanding of their formation and a deep exploration of their growth mechanism is required. In the present work, the formation of b...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-03, Vol.24 (6), p.1040
Main Authors: Reizer, Edina, Csizmadia, Imre G, Palotás, Árpád B, Viskolcz, Béla, Fiser, Béla
Format: Article
Language:English
Subjects:
Anthracene
benz(a)anthracene
Benz(a)Anthracenes - chemistry
Benz(a)Anthracenes - toxicity
benzo(a)pyrene
Benzo(a)pyrene - chemistry
Benzo(a)pyrene - toxicity
Carcinogens
Carcinogens - chemistry
Carcinogens - toxicity
Chemical speciation
Chemistry
Chrysene
Chrysenes - chemistry
Developing countries
DFT
Energy levels
growth mechanism
Humans
Hydrogen
Hydrogen - chemistry
LDCs
Molecular Structure
PAH
Pollutants
Polycyclic aromatic hydrocarbons
Polycyclic Aromatic Hydrocarbons - chemistry
Polycyclic Aromatic Hydrocarbons - toxicity
Pyrene
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Summary:The formation of polycyclic aromatic hydrocarbons (PAHs) is a strong global concern due to their harmful effects. To help the reduction of their emissions, a crucial understanding of their formation and a deep exploration of their growth mechanism is required. In the present work, the formation of benzo(a)pyrene was investigated computationally employing chrysene and benz(a)anthracene as starting materials. It was assumed a type of methyl addition/cyclization (MAC) was the valid growth mechanism in this case. Consequently, the reactions implied addition reactions, ring closures, hydrogen abstractions and intramolecular hydrogen shifts. These steps of the mechanism were computed to explore benzo(a)pyene formation. The corresponding energies of the chemical species were determined via hybrid density funcional theory (DFT), B3LYP/6-31+G(d,p) and M06-2X/6-311++G(d,p). Results showed that the two reaction routes had very similar trends energetically, the difference between the energy levels of the corresponding molecules was just 6.13 kJ/mol on average. The most stable structure was obtained in the benzo(a)anthracene pathway.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24061040