Journal Title
Title of Journal: Struct Chem
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Abbravation: Structural Chemistry
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Authors: Amir Khojastehnezhad Hossein Eshghi Farid Moeinpour Mehdi Bakavoli Mohammad Izadyar Javad Tajabadi
Publish Date: 2015/11/24
Volume: 27, Issue: 4, Pages: 1041-1047
Abstract
The mechanism regio and stereoselectivity of 13dipolar cycloaddition 13DC of 2ethylthio4phenyl1azetin 1 with benzonitrile oxide 2a 2aminobenzonitrile oxide 2b and 2azidobenzonitrile oxide 2c has been investigated by density functional theorybased reactivity indices and activation energy calculations at B3LYP/631Gdp level of theory in the gas and solvent phase Thermodynamic and kinetic parameters of the possible ortho/meta regioisomeric and endo/exo stereoisomeric pathways have been determined In order to rationalize complete endo selective fashion provided by these 13DC cycloadditions a natural steric analysis between NLMOs ij for TS1ox and TS1on and also a secondorder interaction energy E 2 analysis between the donor–acceptor orbitals in these TSs were carried out In all cases the ortho pathways are more favorable compared to the meta alternatives and it is found that the endo pathway is preferred Our results show that these cycloadditions follow an asynchronous onestep mechanism with a nonpolar character Theoretical data are in good agreement with the experimental results
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