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RAS Chemistry & Material ScienceХимическая физика Advances in Chemical Physics

  • ISSN (Print) 0207-401X
  • ISSN (Online) 3034-6126

Reaction of atomic fluorine with benzene

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PII
10.31857/S0207401X24060018-1
DOI
10.31857/S0207401X24060018
Publication type
Article
Status
Published
Authors
S. O. Adamson
  • Affiliation: Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences
Volume/ Edition
Volume 43 / Issue number 6
Pages
3-15
Abstract
Benzene is one of the most common classes of chemicals in industry. As a rule, it enters the atmosphere as a result of man-made accidents, during the evaporation of solvents, etc. Benzene and its derivatives are toxic and have a negative impact on the environment and the human body. Therefore, issues of benzene transformation in the atmosphere are of increased interest. In present work, the structures and electronic energies of equilibrium configurations and transition complexes of the C₆H₆ F and C₆H₆F⁺ systems are calculated using the density functional theory. It has been shown that the interaction of benzene with atomic fluorine can proceed through two channels, i.e. the elimination of hydrogen with the formation of a phenyl radical and the addition of a fluorine atom with the formation of an ipso-fluorocyclohexadienyl radical. It has been established that for the dissociation of ipso-fluorocyclohexadienyl radical into fluorobenzene and atomic hydrogen, it is necessary to expend about 27 kcal/mol. This indicates a low probability of this process occurring at low temperatures. Under experimental conditions, when the temperature of fluorine atoms is about 1000 K, the ipso-fluorocyclohexadienyl radical decomposes to form fluorobenzene. In this case, the occurrence of secondary reactions is unlikely. The conclusions drawn from the analysis of the results of quantum chemical calculations are in good agreement with the experimental data.
Keywords
газофазная реакция механизм реакции гамильтониан реакционного пути бензол атомарный фтор теория функционала плотности
Date of publication
14.09.2025
Year of publication
2025
Number of purchasers
0
Views
3

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