Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives
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Fecha
2015-06
Profesor/a Guía
Facultad/escuela
Idioma
en
Título de la revista
ISSN de la revista
Título del volumen
Editor
Wiley-VCH Verlag
Nombre de Curso
Licencia CC
Atribución 4.0 Internacional (CC BY 4.0)
Licencia CC
https://creativecommons.org/licenses/by/4.0/deed.es
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). © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Notas
Indexación: Scopus
Palabras clave
adaptive natural partitioning analysis, aromaticity, fluorinated benzenes, induced magnetic fields, magnetically induced current density
Citación
Chemistry Volume 4, Issue 3, Pages 302 - 3071 June 2015
DOI
10.1002/open.201402110