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- Title
DFT investigation of the thermodynamics and mechanism of electrophilic chlorination and iodination of arenes.
- Authors
Filimonov, Victor; Poleshchuk, Oleg; Krasnokutskaya, Elena; Frenking, Gernot
- Abstract
Quantum chemical calculations at the B3LYP/6-311G* level have been carried out in order to investigate the reaction mechanisms of the iodination of benzene and its monosubstituted derivatives with ICl, I, I and reagents containing N-I and O-I bonds as the iodinating agents. The results are compared with those obtained for chlorination by Cl and Cl, both in the gas phase and in methanol solution using the PCM solvent model. We have also used the MP2/DGDZVP level of theory and the IEFPCM model to perform comparisons in a few cases. The thermodynamic parameters for the reactions have been calculated, the structures of the intermediate products (π- and σ-complexes) and transition states have been optimized, and the profiles of the free energy surfaces have been constructed.
- Subjects
QUANTUM chemistry; BENZENE; AROMATIC compounds; THERMODYNAMICS; PHYSICS
- Publication
Journal of Molecular Modeling, 2011, Vol 17, Issue 11, p2759
- ISSN
1610-2940
- Publication type
Article
- DOI
10.1007/s00894-011-0964-0