Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives

Juan J. Torres-Vega, Alejandro Vásquez-Espinal, Lina Ruiz, María A. Fernández-Herrera, Luis Alvarez-Thon, Gabriel Merino, William Tiznado

Resultado de la investigación: Contribución a una revistaArtículo

21 Citas (Scopus)

Resumen

The electron delocalization of benzene (C6H6) and hexafluorobenzene (C6F6) was analyzed in terms of the induced magnetic field, nucleus-independent chemical shift (NICS), and ring current strength (RCS). The computed out-of-plane component of the induced magnetic field at a distance (r) greater than or equal to 1.0 Å above the ring center correlates well (R2>0.99) with the RCS value. According to these criteria, fluorination has two effects on the C6 skeleton; concomitantly, the resonant effects diminish the π electron delocalization and the inductive effects decrease the charge density at the ring center and therefore reduce the magnitude of the paratropic current generated in this region. The equilibrium between both effects decreases aromaticity in the fluorinated benzene derivatives. These results can be extrapolated to determine the aromaticity of any derivative within the series of fluorinated benzene derivatives (C6H(6-n)Fn, where n=1-5).

Idioma originalInglés
Páginas (desde-hasta)302-307
Número de páginas6
PublicaciónChemistryOpen
Volumen4
N.º3
DOI
EstadoPublicada - 1 jun 2015

Áreas temáticas de ASJC Scopus

  • Química (todo)

Huella Profundice en los temas de investigación de 'Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives'. En conjunto forman una huella única.

  • Citar esto

    Torres-Vega, J. J., Vásquez-Espinal, A., Ruiz, L., Fernández-Herrera, M. A., Alvarez-Thon, L., Merino, G., & Tiznado, W. (2015). Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives. ChemistryOpen, 4(3), 302-307. https://doi.org/10.1002/open.201402110