Abstract
Throwing a curve: The first example of a through-bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic-substituted sumanenes. Methyl- and hydroxysumanene favor the endo-R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic C-H bond with the bowl.
| Original language | English |
|---|---|
| Pages (from-to) | 7314-7316 |
| Number of pages | 3 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 52 |
| Issue number | 28 |
| DOIs | |
| Publication status | Published - 2013 Jul 8 |
| Externally published | Yes |
Keywords
- conformation analysis
- density functional calculations
- hyperconjugation
- through-bond interactions
- through-space interactions
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Higashibayashi, S., Onogi, S., Srivastava, H. K., Sastry, G. N., Wu, Y. T., & Sakurai, H. (2013). Stereoelectronic effect of curved aromatic structures: Favoring the unexpected endo conformation of benzylic-substituted sumanene. Angewandte Chemie - International Edition, 52(28), 7314-7316. https://doi.org/10.1002/anie.201303134