A further exploration of a nucleophilicity index based on the gas-phase ionization potentials

Paula Jaramillo, Luis R. Domingo, Eduardo Chamorro, Patricia Pérez

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

246 Citas (Scopus)

Resumen

An empirical nucleophilicity index based on the gas-phase ionization potentials has been recently shown to be useful categorizing and settling the nucleophilicity power of a series of captodative ethylenes reacting in cycloaddition reactions (L.R. Domingo, E. Chamorro, P. Pérez, Journal of Organic Chemistry 73 (2008) 4615-4624). In the present work, the applicability of such model is tested within a broader series of substituted alkenes, substituted aromatic compounds and simple nucleophilic molecules. This index obtained within a Koopman's theorem framework has been evaluated here in both gas and solution phases for several well-known nucleophiles. These results are found to be linearly correlated. Finally, the feasibility of the predictive character of this index has been discussed in comparison to the available experimental nucleophilicities of some amines in water. These results further support and validate the usefulness of such approximation in the modeling of the global nucleophilicity.

Idioma originalInglés
Páginas (desde-hasta)68-72
Número de páginas5
PublicaciónJournal of Molecular Structure: THEOCHEM
Volumen865
N.º1-3
DOI
EstadoPublicada - 30 sep 2008

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Física de la materia condensada
  • Química física y teórica

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