title: Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives.
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 (R (2)>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)F n , where n=1-5).
authors.affiliation: Doctorado en Fisicoquímica Molecular, Facultad de Ciencias Exactas, Universidad Andres Bello República 275, Santiago, Chile.
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Torres-Vega
authors.affiliation: Doctorado en Fisicoquímica Molecular, Facultad de Ciencias Exactas, Universidad Andres Bello República 275, Santiago, Chile.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Vásquez-Espinal
authors.affiliation: Centro de Investigación Biomédica, Universidad Autónoma de Chile Llano Subercaseaux 2801, Santiago, Chile.
authors.forename: Lina
authors.initials: L
authors.lastname: Ruiz
authors.affiliation: Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados, Unidad Mérida Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, CP., 97310, Mérida, Yuc., Mexico.
authors.forename: María A
authors.initials: MA
authors.lastname: Fernández-Herrera
authors.affiliation: Departamento de Ciencias Físicas, Facultad de Ciencias Exactas, Universidad Andres Bello República 220, Santiago, Chile.
authors.forename: Luis
authors.initials: L
authors.lastname: Alvarez-Thon
authors.affiliation: Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados, Unidad Mérida Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, CP., 97310, Mérida, Yuc., Mexico.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Merino
authors.affiliation: Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello República 275, Santiago, Chile.
authors.forename: William
authors.initials: W
authors.lastname: Tiznado
keywords: adaptive natural partitioning analysis; aromaticity; fluorinated benzenes; induced magnetic fields; magnetically induced current density