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

Research output: Contribution to journalArticle

21 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)302-307
Number of pages6
JournalChemistryOpen
Volume4
Issue number3
DOIs
Publication statusPublished - 1 Jun 2015

Keywords

  • adaptive natural partitioning analysis
  • aromaticity
  • fluorinated benzenes
  • induced magnetic fields
  • magnetically induced current density

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives'. Together they form a unique fingerprint.

  • Cite this

    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