Theoretical study of the regioselectivity of successive 1,3-butadiene Diels-Alder cycloadditions to C{sub 60}
- Universitat de Girona (Spain)
The possibility of successive Diels-Alder cycloadditions of 1,3-butadiene to C{sub 60} has been studied theoretically by means of the AM1 semiempirical method. The nine unique possible reaction pathways leading to the experimentally observed T{sub h}-symmetric hexakisadduct have been described, and the most thermodynamically favored has been analyzed in more detail. The enthalpy barrier for the cycloaddition changes from 16.2 kcal/mol in the formation of the monoadduct to 17.8 kcal/mol for the hexakisadduct, increasing slightly with successive attacks. However, once the hexakisadduct is reached, addition of a new 1,3-butadiene has an enthalpy barrier as high as 35.5 kcal/mol, in agreement with the fact that experimentally the heptakisadduct has not yet been observed. 26 refs., 2 figs., 2 tabs.
- OSTI ID:
- 420900
- Journal Information:
- Journal of the American Chemical Society, Vol. 118, Issue 37; Other Information: PBD: 18 Sep 1996
- Country of Publication:
- United States
- Language:
- English
Similar Records
The [C{sub 6}H{sub 10}]{sup {sm{underscore}bullet}+} hypersurface: The parent radical cation Diels-Alder reaction
Pathways for the reaction of the butadiene radical cation, [C{sub 4}H{sub 6}]{sup {sm{underscore}bullet}+}, with ethylene