Predicting and Understanding the Reactivity of Aza[60]fullerenes

The Diels–Alder reactivity of C59NH azafullerene has been explored computationally. The regioselectivity of the process and the factors controlling the reduced reactivity of this system with respect to the parent C60 fullerene have been analyzed in detail by using the activation strain model of reac...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-01, Vol.82 (1), p.754-758
Main Authors: García-Rodeja, Yago, Solà, Miquel, Fernández, Israel
Format: Article
Language:English
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Summary:The Diels–Alder reactivity of C59NH azafullerene has been explored computationally. The regioselectivity of the process and the factors controlling the reduced reactivity of this system with respect to the parent C60 fullerene have been analyzed in detail by using the activation strain model of reactivity and the energy decomposition analysis method. It is found that the presence of the nitrogen atom and the CH fragment in the fullerene reduces the interaction between the deformed reactants along the entire reaction coordinate.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02424