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Nonclassical Carbocations as C−H Hydrogen Bond Donors

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journal contribution
posted on 2006-04-13, 00:00 authored by Mihaela D. Bojin, Dean J. Tantillo
Computed [B3LYP/6-31+G(d,p) and MP2/6-31+G(d,p)] structures and binding energies for complexes of nonclassical cations (carbonium ions) with ammonia, in the gas phase and several solvents, are described. Overall, nonclassical cations are found to be competent C−H hydrogen bond donors. The potential relevance of the C−H···N interactions holding the carbocation·amine complexes together for enzyme-catalyzed terpenoid synthesis is discussed.

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