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Internet Electronic Journal of Molecular Design - IEJMD, ISSN 1538-6414, CODEN IEJMAT
| ABSTRACT - Internet Electron. J. Mol. Des. February 2007, Volume 6, Number 2, 36-46 |
A Computational Theoretical Study of the Diels-Alder Reaction Between β-ionone
and Maleic Anhydride. Influence of Lewis Acid Catalyst, and Inclusion of Solvent Effects
Hind Dirhoussi and Abdelouahid Sbai
Internet Electron. J. Mol. Des. 2007, 6, 36-46
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Abstract:
In order to contribute to a better understanding of the stereochemical outcome of
the Diels-Alder reaction between β-ionone and maleic anhydride, the presence of
Lewis acid catalyst modeled by the BH3 and the inclusion of solvent effects are
analyzed and discussed. The reaction between β-ionone and maleic anhydride
takes place through synchronous transition structures. The transition structure of
the exo attack is more stable than the endo one. The Diels-Alder reaction of the
β-ionone and maleic anhydride has been studied using density functional and
conventional ab-initio methods. The transition structure of the exo attack is more
stable than the endo one. The inclusion of Lewis acid catalyst increases the
asynchronicity of transition states and decreases the activation energies of the
cycloaddition process, while the inclusion of solvent effect produces a significant
increase of the exo selectivity. This study shows that the DFT calculations are
useful to obtain qualitatively correct result.
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