The Regioselectivity of Bingel–Hirsch Cycloadditions on Isolated Pentagon Rule Endohedral Metallofullerenes |
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| Authors: | Dr. Marc Garcia‐Borràs Dr. Maira R. Cerón Dr. Sílvia Osuna Dr. Marta Izquierdo Dr. Josep M. Luis Prof. Dr. Luis Echegoyen Prof. Dr. Miquel Solà |
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| Affiliation: | 1. Institut de Química Computacional i Catàlisi (IQCC), Departament de Química, Universitat de Girona, Girona, Catalonia, Spain;2. Department of Chemistry, University of Texas at El Paso, El Paso, Texas, USA |
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| Abstract: | In this work, the Bingel–Hirsch addition of diethylbromomalonate to all non‐equivalent bonds of Sc3N@D3h‐C78 was studied using density functional theory calculations. The regioselectivities observed computationally allowed the proposal of a set of rules, the predictive aromaticity criteria (PAC), to identify the most reactive bonds of a given endohedral metallofullerene based on a simple evaluation of the cage structure. The predictions based on the PAC are fully confirmed by both the computational and experimental exploration of the Bingel–Hirsch reaction of Sc3N@D5h‐C80, thus indicating that these rules are rather general and applicable to other isolated pentagon rule endohedral metallofullerenes. |
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| Keywords: | aromaticity cage compounds density-functional calculations fullerenes supramolecular chemistry |
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