Dinadayalane, T. C. ; Deepa, S. ; Reddy, A. Srinivas ; Sastry, G. Narahari (2004) Density functional theory study on the effect of substitution and ring annelation to the rim of corannulene The Journal of Organic Chemistry, 69 (23). pp. 8111-8114. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo048850a
Related URL: http://dx.doi.org/10.1021/jo048850a
Abstract
B3LYP/6-311G** calculations indicate that annelation of a five-membered ring to the rim of corannulene and substitution to all the rim carbons lowers the barrier for bowl-to-bowl inversion. Singlet−triplet energy differences, frontier orbital analysis, and nucleus-independent chemical shift (NICS) values indicate significant enhancement of the reactivity when the substitutions involve exocyclic double bonds. Bowl-to-bowl inversion barrier, curvature, and reactivity for unsaturated and saturated five-membered ring-annelated corannulenes are analogous to decamethyl- and decamethylene-substituted corannulenes.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 106982 |
| Deposited On: | 02 Aug 2017 07:14 |
| Last Modified: | 02 Aug 2017 07:14 |
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