Literature DB >> 22948533

Is C60 buckminsterfullerene aromatic?

Zhongfang Chen1, Judy I Wu, Clémence Corminboeuf, Jonathan Bohmann, Xin Lu, Andreas Hirsch, Paul von Ragué Schleyer.   

Abstract

C(60) 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 C(60) 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. C(20)(2+) (18 π electrons) and C(60)(10+) (50 π electrons) are spherically π aromatic, but C(20) (20 π electrons) and C(60) (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 C(60)(6-) and the lack of π aromaticity of the 72 π electron C(48)N(12) and C(60)(12-).

Year:  2012        PMID: 22948533     DOI: 10.1039/c2cp42146a

Source DB:  PubMed          Journal:  Phys Chem Chem Phys        ISSN: 1463-9076            Impact factor:   3.676


  6 in total

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5.  Identifying Molecular Structural Aromaticity for Hydrocarbon Classification.

Authors:  Ryan C Fortenberry; Carlie M Novak; Timothy J Lee; Partha P Bera; Julia E Rice
Journal:  ACS Omega       Date:  2018-11-27

6.  Three-Dimensional Fully π-Conjugated Macrocycles: When 3D-Aromatic and When 2D-Aromatic-in-3D?

Authors:  Ouissam El Bakouri; Dariusz W Szczepanik; Kjell Jorner; Rabia Ayub; Patrick Bultinck; Miquel Solà; Henrik Ottosson
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  6 in total

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