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

Zhongfang Chen*, Haijun Jiao, Damian Moran, Andreas Hirsch, Walter Thiel, Paul von Ragué Schleyer

*Corresponding author for this work

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

B3LYP density functional calculations were performed on two S6 symmetrical isomers (I and II) of C48X12 (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 C60Cl12.

Original languageEnglish
Pages (from-to)726-730
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume16
Issue number10
DOIs
Publication statusPublished - Oct 2003
Externally publishedYes

Keywords

  • Aromaticity
  • Heterofullerenes
  • Isomerism
  • NICS
  • Stability

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