title: A comparison of the chemical reactivity of naringenin calculated with the M06 family of density functionals.
abstract: BACKGROUND
  Chemicals generically referred to as flavonoids belong to the group of phenolic compounds and constitute an important group of secondary metabolites due to their applications as well as their biochemical properties. Flavonoids, which share a common benzo- γ-pyrone structure, constitute a kind of compound which are highly ubiquitous in the plant kingdom.
  
  
  RESULTS
  The M06 family of density functionals has been assessed for the calculation of the molecular structure and properties of the Naringenin flavonoid. The chemical reactivity descriptors have been calculated through Conceptual DFT. The active sites for nucleophilic and electrophilic attacks have been chosen by relating them to the Fukui function indices and the dual descriptor f(2)(r). A comparison between the descriptors calculated through vertical energy values and those arising from the Koopmans' theorem approximation have been performed in order to check for the validity of the last procedure.
  
  
  CONCLUSIONS
  The M06 family of density functionals (M06, M06L, M06-2X and M06-HF) used in the present work leads to the same qualitatively and quantitatively similar description of the chemistry and reactivity of the Naringenin molecule, yielding reasonable results. However, for the case of the M06-2X and M06-HF density functionals, which include a large portion of HF exchange, the calculations considering the validity of the Koopmans' theorem lead to negative electron affinities.
authors.affiliation: NANOCOSMOS Virtual Lab, CIMAV, Miguel de Cervantes 120, Complejo Industrial Chihuahua, Chihuahua, Chih 31109, Mexico. daniel.glossman@cimav.edu.mx.
authors.forename: Daniel
authors.initials: D
authors.lastname: Glossman-Mitnik
references.citation: J Phys Chem A. 2007 Mar 15;111(10):1966-70
references.pmid: 17305319
references.citation: Chemistry. 2007;13(29):8240-7
references.pmid: 17639522
references.citation: J Chem Phys. 2006 May 21;124(19):194107
references.pmid: 16729803
references.citation: J Phys Chem A. 2005 Jan 13;109(1):205-12
references.pmid: 16839107
references.citation: J Phys Chem A. 2009 Sep 17;113(37):10068-74
references.pmid: 19702288
references.citation: J Phys Chem A. 2009 Jul 30;113(30):8660-7
references.pmid: 19580251
references.citation: J Phys Chem B. 2009 May 7;113(18):6378-96
references.pmid: 19366259
references.citation: Phys Rev Lett. 1996 Oct 28;77(18):3865-3868
references.pmid: 10062328
references.citation: Chem Rev. 2003 May;103(5):1793-873
references.pmid: 12744694
references.citation: Molecules. 2010 Jun 24;15(7):4490-510
references.pmid: 20657373
references.citation: Phys Chem Chem Phys. 2008 Dec 28;10(48):7239-46
references.pmid: 19060968
references.citation: Acc Chem Res. 2008 Feb;41(2):157-67
references.pmid: 18186612