Next Article in Journal
Isolation of a Novel Flavanonol and an Alkylresorcinol with Highly Potent Anti-Trypanosomal Activity from Libyan Propolis
Previous Article in Journal
Evidence for the Formation of Difluoroacetic Acid in Chlorofluorocarbon-Contaminated Ground Water
Previous Article in Special Issue
First-Principles Study of the Reaction between Fluorinated Graphene and Ethylenediamine
Article Menu

Export Article

Open AccessArticle
Molecules 2019, 24(6), 1040; https://doi.org/10.3390/molecules24061040

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

1
Institute of Chemistry, University of Miskolc, Miskolc-Egyetemváros, H-3515 Miskolc, Hungary
2
Department of Chemisrty, University of Toronto, Toronto, M5S 1A1 Ontario, Canada
3
Institute of Energy and Quality Affairs, University of Miskolc, Miskolc-Egyetemváros, H-3515 Miskolc, Hungary
4
Ferenc Rákóczi II. Transcarpathian Hungarian Institute, UA-90200 Beregszász, Transcarpathia, Ukraine
*
Author to whom correspondence should be addressed.
Academic Editor: Maxim L. Kuznetsov
Received: 17 January 2019 / Revised: 5 March 2019 / Accepted: 11 March 2019 / Published: 15 March 2019
(This article belongs to the Special Issue Theoretical Investigations of Reaction Mechanisms)
Full-Text   |   PDF [1832 KB, uploaded 15 March 2019]   |  

Abstract

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. View Full-Text
Keywords: PAH; growth mechanism; DFT; chrysene; benz(a)anthracene; benzo(a)pyrene PAH; growth mechanism; DFT; chrysene; benz(a)anthracene; benzo(a)pyrene
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Reizer, E.; Csizmadia, I.G.; Palotás, Á.B.; Viskolcz, B.; Fiser, B. Formation Mechanism of Benzo(a)pyrene: One of the Most Carcinogenic Polycyclic Aromatic Hydrocarbons (PAH). Molecules 2019, 24, 1040.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top