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, Journal Name: Journal of the American Chemical Society Journal Issue: 37 Vol. 118; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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