Theoretical analysis of reactions of electrophilic iodination and chlorination of benzene and polycyclic arenes in density functional theory approximation

V. D. Filimonov, E. A. Krasnokytskaya, O. Kh Poleshchuk, Yu A. Lesina

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Quantum-chemical method DFT B3LYP/6-311G*was applied to stage by stage thermodynamic calculation of reactions of electrophilic iodination of benzene, naphthalene, phenanthrene, and anthracene with iodine and iodine monochloride, and comparison with chlorination reactions was performed. The main distinction of iodination process from chlorination was an enhanced reversibility owing to protodeiodination. The reversibility of iodination grows with the electron-donor properties of aromatic substrates. The calculations permit an assumption that the chlorination of anthracene and phenanthrene with iodine monochloride occurs most probably through stages of electrophilic iodination-dehydroiodination.

Original languageEnglish
Pages (from-to)681-687
Number of pages7
JournalRussian Journal of Organic Chemistry
Volume44
Issue number5
DOIs
Publication statusPublished - May 2008

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Chlorination
Benzene
Density functional theory
Discrete Fourier transforms
Iodine
Thermodynamics
Electrons
Substrates
iodine monochloride
phenanthrene
anthracene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Quantum-chemical method DFT B3LYP/6-311G*was applied to stage by stage thermodynamic calculation of reactions of electrophilic iodination of benzene, naphthalene, phenanthrene, and anthracene with iodine and iodine monochloride, and comparison with chlorination reactions was performed. The main distinction of iodination process from chlorination was an enhanced reversibility owing to protodeiodination. The reversibility of iodination grows with the electron-donor properties of aromatic substrates. The calculations permit an assumption that the chlorination of anthracene and phenanthrene with iodine monochloride occurs most probably through stages of electrophilic iodination-dehydroiodination.",
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AU - Poleshchuk, O. Kh

AU - Lesina, Yu A.

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