Issue 43, 2012
From the journal:

Physical Chemistry Chemical Physics

Is C60 buckminsterfullerene aromatic?

Zhongfang Chen,*a   Judy I. Wu,b   Clémence Corminboeuf,c   Jonathan Bohmann,d   Xin Lu,e   Andreas Hirschf  and  Paul von Ragué Schleyer*b  

* Corresponding authors

a Department of Chemistry, University of Puerto Rico, San Juan, USA
E-mail: zhongfangchen@gmail.com

b Center for Computational Chemistry, Department of Chemistry, University of Georgia, Athens, USA
E-mail: schleyer@chem.uga.edu

c Department of Chemistry, Ecole polytechnique fédérale de Lausanne, Lausanne, Switzerland

d Synthesis and Drug Delivery Group, Southwest Research Institute, San Antonio, USA

e State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China

f Institute of Organic Chemistry LS II, University of Erlangen-Nuremberg, 91054 Erlangen, Germany

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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Article information

DOI
https://doi.org/10.1039/C2CP42146A
Article type
Paper
Submitted
26 Jun 2012
Accepted
10 Aug 2012
First published
13 Aug 2012

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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