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Journal of Chemistry
Volume 2018 (2018), Article ID 1958047, 10 pages
Research Article

The Substitution Effect on Reaction Enthalpies of Antioxidant Mechanisms of Juglone and Its Derivatives in Gas and Solution Phase: DFT Study

1Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon
2Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon
3Department of Inorganic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon

Correspondence should be addressed to Désiré Bikélé Mama; rf.oohay@amamelekib

Received 21 October 2017; Revised 27 December 2017; Accepted 9 January 2018; Published 16 April 2018

Academic Editor: Dario Pasini

Copyright © 2018 Aymard Didier Tamafo Fouegue 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.


We examined the structure-reaction enthalpies-antioxidant activity relationship of the molecule library built around juglone and its derivatives at B3LYP/6-31+G(d,p) level. Three major antioxidant mechanisms (hydrogen atom transfer (HAT), single electron transfer-proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET)) have been investigated in five solvents and in the gas phase. The delocalization of the unpaired electrons in the radicals or cation radicals has been explored by the natural bond orbital analysis and the interpretation of spin density maps. The results obtained have proven that the HAT mechanism is the thermodynamically preferred mechanism in the gas phase. But, in the solution phase, the SPLET mechanism has been shown to be more predominant than HAT. The reactivity order of compounds towards selected reactive oxygen species has also been studied.