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Molecules 2016, 21(11), 1422; doi:10.3390/molecules21111422

Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations

1
Departament of Chemistry, Tecnológico de Monterrey, Av. E. Garza Sada 2501 Sur, Monterrey 64849, N.L., Mexico
2
Facultad de Ciencias Químicas, Universidad Autónoma de Nuevo León, Av. Pedro de Alba S-N Cd. Universitaria, San Nicolás De Los Garza 66451, N.L., Mexico
3
School of Engineering and Science, Tecnológico de Monterrey, Av. E. Garza Sada 2501 Sur, Monterrey 64849, N.L., Mexico
Current address: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Albert J. Fry
Received: 2 September 2016 / Revised: 11 October 2016 / Accepted: 18 October 2016 / Published: 27 October 2016
(This article belongs to the Special Issue Organic Electrochemistry)
View Full-Text   |   Download PDF [1620 KB, uploaded 27 October 2016]   |  

Abstract

Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure–electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of –OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins ( R 2 = 0.98 ). We analyzed the effects that position and number of –OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules. View Full-Text
Keywords: voltammetry; antioxidants; flavonoids; ab initio; electron density distribution voltammetry; antioxidants; flavonoids; ab initio; electron density distribution
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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. (CC BY 4.0).

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Arroyo-Currás, N.; Rosas-García, V.M.; Videa, M. Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations. Molecules 2016, 21, 1422.

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