Nonclassical 21-Homododecahedryl Cation Rearrangement Revisited

Said Jalife, Sukanta Mondal, Edison Osorio, José Luis Cabellos, Gerardo Martínez-Guajardo, María A. Fernández-Herrera, Gabriel Merino

Resultado de la investigación: Contribución a una revistaArtículo

2 Citas (Scopus)

Resumen

The degenerate rearrangement in the 21-homododecahedryl cation (1) has been studied via density functional theory computations and Born-Oppenheimer Molecular Dynamics simulations. Compound 1 can be described as a highly fluxional hyperconjugated carbocation. Complete scrambling of 1 can be achieved by the combination of two unveiled barrierless processes. The first one is a "rotation" of one of the six-membered rings via a 0.8 kcal·mol-1 barrier, and the second one is a slower interconvertion between two hyperconjomers via an out-of-plane methine bending (ΔG‡ = 4.0 kcal·mol-1).

Idioma originalInglés
Páginas (desde-hasta)1140-1142
Número de páginas3
PublicaciónOrganic Letters
Volumen18
N.º5
DOI
EstadoPublicada - 4 mar 2016

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    Jalife, S., Mondal, S., Osorio, E., Cabellos, J. L., Martínez-Guajardo, G., Fernández-Herrera, M. A., & Merino, G. (2016). Nonclassical 21-Homododecahedryl Cation Rearrangement Revisited. Organic Letters, 18(5), 1140-1142. https://doi.org/10.1021/acs.orglett.5b03558