Title
Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives
Date Issued
01 June 2015
Access level
open access
Resource Type
journal article
Author(s)
Vásquez-Espinal A.
Ruiz L.
Fernández-Herrera M.A.
Alvarez-Thon L.
Merino G.
Tiznado W.
Universidad Andres Bello
Publisher(s)
Wiley-VCH Verlag
Abstract
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).
Start page
302
End page
307
Volume
4
Issue
3
Language
English
OCDE Knowledge area
Química orgánica
Química
Subjects
Scopus EID
2-s2.0-85027916692
Source
ChemistryOpen
ISSN of the container
18790852
Sources of information:
Directorio de Producción Científica
Scopus