Higashibayashi, Shuhei ; Onogi, Satoru ; Srivastava, Hemant Kumar ; Sastry, G. Narahari ; Wu, Yao-Ting ; Sakurai, Hidehiro (2013) Stereoelectronic effect of curved aromatic structures: favoring the unexpected endo conformation of benzyli-substituted sumanene Angewandte Chemie International Edition, 52 (28). pp. 7314-7316. ISSN 1433-7851
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.20...
Related URL: http://dx.doi.org/10.1002/anie.201303134
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[BOND]H bond with the bowl.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
| Keywords: | Conformation Analysis; Density Functional Calculations; Hyperconjugation; Through-Bond Interactions; Through-Space Interactions |
| ID Code: | 108617 |
| Deposited On: | 27 Jul 2017 12:52 |
| Last Modified: | 27 Jul 2017 12:52 |
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