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Journal of Chemistry
Volume 2017, Article ID 9254831, 5 pages
https://doi.org/10.1155/2017/9254831
Research Article

Theoretical Study about the Effect of Halogen Substitution on the Reactivity of Antitumor 3-Formylchromones and Their Free Radicals

1Programa Institucional de Fomento a la Investigación, Desarrollo e Innovación, Universidad Tecnológica Metropolitana, Ignacio Valdivieso 2409, Casilla 9845, 8940577 Santiago, Chile
2Departamento de Química, Facultad de Ciencias, Universidad de Chile, Las Palmeras 3425, Casilla 653, 7800003 Santiago, Chile
3Instituto de Química de Recursos Naturales, Universidad de Talca, Av. Lircay s/n, Casilla 747, 3460000 Talca, Chile

Correspondence should be addressed to Maximiliano Martínez-Cifuentes; lc.metu@zenitramm and Ramiro Araya-Maturana; lc.aclatu@ayarar

Received 29 December 2016; Accepted 2 February 2017; Published 21 February 2017

Academic Editor: Pedro M. Mancini

Copyright © 2017 Maximiliano Martínez-Cifuentes et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The mandatory presence of a chlorine atom on the aromatic ring of 6-hydroxy-3-formyl angular chromones, on the respiration inhibition of mammary carcinoma mouse, is explained through a computational study of these compounds. This study analyzes the reactivity of the neutral molecules and their free radicals, in gas phase and with water solvation, incorporated by the polarizable continuum medium (PCM) approach. Electrophilic reactivities were evaluated using Fukui () and Parr () functions. The stabilities of radical species formed by the abstraction of a hydrogen atom from the O-H bond were evaluated by bond dissociation enthalpy (BDE) and spin density (SD) calculations. This study has potential implications for the design of chromone analogues as anticancer compounds.