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: Article

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

Huella dactilar

Benzene Derivatives
Magnetic fields
Fluorination
Electrons
Chemical shift
Benzene
Charge density
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

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
Torres-Vega, Juan J. ; Vásquez-Espinal, Alejandro ; Ruiz, Lina ; Fernández-Herrera, María A. ; Alvarez-Thon, Luis ; Merino, Gabriel ; Tiznado, William. / Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives. En: ChemistryOpen. 2015 ; Vol. 4, N.º 3. pp. 302-307.
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Torres-Vega, JJ, Vásquez-Espinal, A, Ruiz, L, Fernández-Herrera, MA, Alvarez-Thon, L, Merino, G & Tiznado, W 2015, 'Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives', ChemistryOpen, vol. 4, n.º 3, pp. 302-307. https://doi.org/10.1002/open.201402110

Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives. / Torres-Vega, Juan J.; Vásquez-Espinal, Alejandro; Ruiz, Lina; Fernández-Herrera, María A.; Alvarez-Thon, Luis; Merino, Gabriel; Tiznado, William.

En: ChemistryOpen, Vol. 4, N.º 3, 01.06.2015, p. 302-307.

Resultado de la investigación: Article

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AU - Torres-Vega, Juan J.

AU - Vásquez-Espinal, Alejandro

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AU - Fernández-Herrera, María A.

AU - Alvarez-Thon, Luis

AU - Merino, Gabriel

AU - Tiznado, William

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N2 - 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).

AB - 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).

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Torres-Vega JJ, Vásquez-Espinal A, Ruiz L, Fernández-Herrera MA, Alvarez-Thon L, Merino G y otros. Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives. ChemistryOpen. 2015 jun 1;4(3):302-307. https://doi.org/10.1002/open.201402110