Aromatic stabilization in heterofullerenes C48X12 (X = N, P, B, Si)

Chen Z, Jiao H, Moran DM, Hirsch A, Thiel W, Schleyer P (2003)

Publication Type: Journal article, Original article

Publication year: 2003

Journal

Journal of Physical Organic Chemistry Wiley-Blackwell

Original Authors: Chen Z., Jiao H., Moran D., Hirsch A., Thiel W., Schleyer P.V.R.

Publisher: Wiley-Blackwell

Book Volume: 16

Pages Range: 726-730

Journal Issue: 10

DOI: 10.1002/poc.631

Abstract

B3LYP density functional calculations were performed on two S symmetrical isomers (I and II) of CX (X = N, B, P, Si) heterofullerenes, and their global and local aromaticity were evaluated by nucleus-independent chemical shifts (NICS). Despite the unfavorable heteroatom repulsive interactions, isomer II is more stable than I owing to the combination of global and local aromaticity. The latter arises from the presence of triphenylene units in isomer II. The aromatic stabilization effects found in this study should be taken into account when predicting the most stable isomers of heterofullerenes. The same is true for predictions of the isomers of fullerene adducts such as CCl. Copyright © 2003 John Wiley & Sons, Ltd.

Authors with CRIS profile

Andreas Hirsch Lehrstuhl für Organische Chemie II Paul Schleyer Naturwissenschaftliche Fakultät

Involved external institutions

Max-Planck-Institut für Kohlenforschung (MPI KoFo) / Max Planck Institute for Coal Research DE Germany (DE)

How to cite

APA:

Chen, Z., Jiao, H., Moran, D.M., Hirsch, A., Thiel, W., & Schleyer, P. (2003). Aromatic stabilization in heterofullerenes C48X12 (X = N, P, B, Si). Journal of Physical Organic Chemistry, 16(10), 726-730. https://dx.doi.org/10.1002/poc.631

MLA:

Chen, Zhongfang, et al. "Aromatic stabilization in heterofullerenes C48X12 (X = N, P, B, Si)." Journal of Physical Organic Chemistry 16.10 (2003): 726-730.

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