Next Article in Journal
Antisense Oligonucleotide-Based Therapy for Neuromuscular Disease
Previous Article in Journal
Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents
Previous Article in Special Issue
Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
Article Menu
Issue 4 (April) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(4), 577;

Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones

Programa Institucional de Fomento a la Investigación, Desarrollo e Innovación, Universidad Tecnológica Metropolitana, Ignacio Valdivieso 2409, Casilla 9845, Santiago 8940577, Chile
Laboratorio de Electroquímica del Medio Ambiente, LEQMA, Departamento de Química de los Materiales, Facultad de Química y Biología, Universidad de Santiago de Chile, USACh, Casilla 40, Correo 33, Santiago 9170022, Chile
Departamento de Química, Instituto de Ciencias Básicas, Universidad Técnica de Manabí, Av. Urbina y Che Guevara, Portoviejo 130104, Ecuador
Campus Río Simpson, Universidad de Aysén, Obispo Vielmo 62, Coyhaique 5952039, Chile
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Las Palmeras 3425, Casilla 653, Santiago 7800003, Chile
Instituto de Química de Recursos Naturales, Universidad de Talca, Av. Lircay s/n, Casilla 747, Talca 3460000, Chile
Authors to whom correspondence should be addressed.
Academic Editor: Albert J. Fry
Received: 29 January 2017 / Revised: 14 March 2017 / Accepted: 29 March 2017 / Published: 4 April 2017
(This article belongs to the Special Issue Organic Electrochemistry)
Full-Text   |   PDF [1180 KB, uploaded 4 April 2017]   |  


The rational design of quinones with specific redox properties is an issue of great interest because of their applications in pharmaceutical and material sciences. In this work, the electrochemical behavior of a series of four p-quinones was studied experimentally and theoretically. The first and second one-electron reduction potentials of the quinones were determined using cyclic voltammetry and correlated with those calculated by density functional theory (DFT) using three different functionals, BHandHLYP, M06-2x and PBE0. The differences among the experimental reduction potentials were explained in terms of structural effects on the stabilities of the formed species. DFT calculations accurately reproduced the first one-electron experimental reduction potentials with R2 higher than 0.94. The BHandHLYP functional presented the best fit to the experimental values (R2 = 0.957), followed by M06-2x (R2 = 0.947) and PBE0 (R2 = 0.942). View Full-Text
Keywords: quinones; redox potential; density functional theory; semiquinone; cyclic voltammetry quinones; redox potential; density functional theory; semiquinone; cyclic voltammetry

Graphical abstract

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).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

Martínez-Cifuentes, M.; Salazar, R.; Ramírez-Rodríguez, O.; Weiss-López, B.; Araya-Maturana, R. Experimental and Theoretical Reduction Potentials of Some Biologically Active ortho-Carbonyl para-Quinones. Molecules 2017, 22, 577.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top