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Issue 43, 2012
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Is C60 buckminsterfullerene aromatic?

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Abstract

C60 does not have “superaromatic” or even aromatic character, but is a spherically π antiaromatic and enormously strained species. This explains its very large and positive heat of formation (610 ± 30 kcal mol−1). The π electron character of C60 was analyzed by dissected nucleus independent chemical shifts (NICS). The results were employed to examine the scope and limitations of Hirsch's 2(N + 1)2 spherical aromaticity rule for several globular cages. C202+ (18 π electrons) and C6010+ (50 π electrons) are spherically π aromatic, but C20 (20 π electrons) and C60 (60 π electrons) are spherically π antiaromatic, due to the high paratropicity of their half-filled π subshells. Limitations for Hirsch's rule, for clusters with more than 50 π electrons, are illustrated by e.g. the π aromaticity of the 66 π electron C606− and the lack of π aromaticity of the 72 π electron C48N12 and C6012−.

Graphical abstract: Is C60 buckminsterfullerene aromatic?

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Publication details

The article was received on 26 Jun 2012, accepted on 10 Aug 2012 and first published on 13 Aug 2012


Article type: Paper
DOI: 10.1039/C2CP42146A
Citation: Phys. Chem. Chem. Phys., 2012,14, 14886-14891
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    Is C60 buckminsterfullerene aromatic?

    Z. Chen, J. I. Wu, C. Corminboeuf, J. Bohmann, X. Lu, A. Hirsch and P. V. R. Schleyer, Phys. Chem. Chem. Phys., 2012, 14, 14886
    DOI: 10.1039/C2CP42146A

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