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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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