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 language | English |
|---|---|
| Pages (from-to) | 681-687 |
| Number of pages | 7 |
| Journal | Russian Journal of Organic Chemistry |
| Volume | 44 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - May 2008 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Theoretical analysis of reactions of electrophilic iodination and chlorination of benzene and polycyclic arenes in density functional theory approximation. / Filimonov, V. D.; Krasnokytskaya, E. A.; Poleshchuk, O. Kh; Lesina, Yu A.
In: Russian Journal of Organic Chemistry, Vol. 44, No. 5, 05.2008, p. 681-687.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Theoretical analysis of reactions of electrophilic iodination and chlorination of benzene and polycyclic arenes in density functional theory approximation
AU - Filimonov, V. D.
AU - Krasnokytskaya, E. A.
AU - Poleshchuk, O. Kh
AU - Lesina, Yu A.
PY - 2008/5
Y1 - 2008/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=45249084562&partnerID=8YFLogxK
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U2 - 10.1134/S1070428008050072
DO - 10.1134/S1070428008050072
M3 - Article
VL - 44
SP - 681
EP - 687
JO - Russian Journal of Organic Chemistry
JF - Russian Journal of Organic Chemistry
SN - 1070-4280
IS - 5
ER -