A semiempirical study on the ring-opening process for the cyclopropanone, 2,2-dimethylcyclopropanone, trans-2,3-di-tert-butylcyclopropanone, and spiro(bicyclo[2.2.1]heptane-2.1′-cyclopropan)-2′-one systems in solution
✍ Scribed by R. Castillo; J. Andrés; V. Moliner; V. S. Safont; M. Oliva
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 360 KB
- Volume
- 65
- Category
- Article
- ISSN
- 0020-7608
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✦ Synopsis
flat region. The analysis of the theoretical results shows that the solvent reaction field decreases the energy barriers for the ring-opening processes and a stabilization of the oxyallyl intermediates takes place. The calculated relative barrier heights are in good agreement with the experimental data available, and the trends in the kinetics can be explained primarily by steric interactions. Nevertheless, for the Ž w x X . X spiro bicyclo 2.2.1 heptane-2.1-cyclopropan -2 -one system, it is necessary to include a specific interaction of a discrete molecule of the nucleophilic solvent on the quantum mechanical representation to explain the experimental behavior.