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Comparative study on the N-heterocyclic carbene adducts of Ih-C60, D5h-C70 and Sc3N@Ih-C80

Abstract

We found that the standard B3LYP and dispersion-corrected B3LYP-D3 methods predicted completely opposite energy order for the Lewis acid-base adducts formed by Ih-C60 or D5h-C70 with the normal C2-bound (nNHC) and abnormal C5-bound (aNHC) N-heterocyclic carbenes. By using the validated B3LYP-D3 method and taking the solvent effects into account, the exclusive formations of the nNHC-C60/70 (Li et al. J. Am. Chem. Soc., 2011, 133, 12410–12413) and aNHC-Sc3N@Ih-C80 complexes (Chen et al. Chem. Sci., 2016, 7, 2331–2334) in two recent experiments were suggested to be thermodynamically and kinetically controlled, respectively. In contrast to the reported reactions of endohedral metallofullerenes, aNHC-Sc3N@Ih-C80 hardly isomerizes to the low-energy normal adducts under heat treatment probably due to the substantial energy barrier and excess NHC reagent used in the experiment. Furthermore, the highly regioselective addition of aNHC to the triple-hexagon-junction carbon atom of Sc3N@Ih-C80 was rationalized by using the frontier molecular orbital theory.

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Publication details

The article was received on 25 Apr 2017, accepted on 14 Jun 2017 and first published on 14 Jun 2017


Article type: Paper
DOI: 10.1039/C7CP02696J
Citation: Phys. Chem. Chem. Phys., 2017, Accepted Manuscript
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    Comparative study on the N-heterocyclic carbene adducts of Ih-C60, D5h-C70 and Sc3N@Ih-C80

    P. Jin, L. Yang, C. Liu, M. Chen, Q. Hou, L. Li and Y. Zhao, Phys. Chem. Chem. Phys., 2017, Accepted Manuscript , DOI: 10.1039/C7CP02696J

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