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Title: Density functional theory investigation of electrophilic addition reaction of chlorine to 3,4-benzobicyclo[3.2.1]-octadiene
Authors: Abbasoglu, Rza
Magerramov, Abel
Keywords: Theoretical chemistry
Electrophilic additions
Density functional calculations
Addition reactions
Geometric optimization
Issue Date: Aug-2009
Publisher: CSIR
Abstract: Full geometric optimization of 3,4-benzobicyclo[3.2.1]- octadiene (BBOD) has been carried out by DFT/B3LYP method using the 6-311G(d), 6-311G(d,p) and 6-311+G(d,p) basis sets. The double bond is endo-pyramidalized and its two faces are not equivalent. The BBOD-Cl<sub>2 </sub>system have been investigated by B3LYP/6-311+G(d,p) method and stable configurations determined. The stable configurations of the BBOD-Cl<sub>2 </sub>system correspond to BBOD…Cl<sub>2</sub>(<i style="">exo</i>) and BBOD…Cl<sub>2</sub>(<i style="">endo</i>) molecular complexes which are formed by the exo and endo orientation respectively of Cl<sub>2 </sub>molecule to the double bond of BBOD in axial position. <i style="">Exo</i>-complex is relatively more stable than the <i style="">endo</i>-complex. <i style="">Exo</i>-chloronium cation was found to be more stable than <i style="">endo</i>-chloronium cation by the DFT method. <i style="">Exo</i>-facial selectivity is expected in the addition reaction to BBOD of chlorine. The non-classical delocalized chlorocarbonium cation(IV) is the most stable ion among the cationic intermediates, and the ionic addition reaction occurs via this cation.<b style=""> </b>The mechanism of the addition reaction is also discussed.
Description: 1091-1095
ISSN: 0975-0975 (Online); 0376-4710 (Print)
Appears in Collections:IJC-A Vol.48A(08) [August 2009]

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