jp056965s_si_001.pdf (641.47 kB)
Nonclassical Carbocations as C−H Hydrogen Bond Donors
journal contribution
posted on 2006-04-13, 00:00 authored by Mihaela D. Bojin, Dean J. TantilloComputed [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.