Probing Intramolecular CH−π Interactions in o-Quinodimethane Adducts of [60]Fullerene Using Variable Temperature NMR
The Journal of Organic Chemistry2012Vol. 77(3), pp. 1308–1315
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Abstract
Several o-quinodimethane adducts of [60]fullerene were synthesized and their intramolecular aryl CH-fullerene π interactions were studied using variable temperature-NMR (VT-NMR). Evaluation of the rate constants associated with the first-order transition states for cyclohexene boat-to-boat inversions enables quantification of ΔG(‡) values for each inversion. A comparison between two constitutional isomers, only one of which is capable of intramolecular CH-π interactions, provides a lower limit of 0.95 kcal/mol for each aryl CH-fullerene π interaction.
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