Density Functional Theory Study on the Effect of Substitution and Ring Annelation to the Rim of Corannulene
- 9 October 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (23) , 8111-8114
- https://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.Keywords
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