Oxidation of organic diselenides and ditellurides by H2O2 for bioinspired catalyst design

Marco Bortoli, Francesco Zaccaria, Marco Dalla Tiezza, Matteo Bruschi, Célia Fonseca Guerra, F. Matthias Bickelhaupt, Laura Orian*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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The reactivity of diselenides and ditellurides of general formula (RX)2 (X = Se, Te; R = H, CH3, Ph) toward hydrogen peroxide was studied through a computational approach based on accurate Density Functional Theory (DFT) calculations. The aliphatic and aromatic dichalcogenides have been chosen in light of their activity in glutathione peroxidase (GPx)-like catalytic cycles and their promising features as efficient antioxidant compounds. The reaction products, the energetics and the mechanistic details of these oxidations are discussed. Analogous disulfides are included in our analysis for completeness. We find that the barrier for oxidation of dichalcogenides decreases from disulfides to diselenides to ditellurides. On the other hand, variation of the substituents at the chalcogen nucleus has relatively little effect on the reactivity.

Original languageEnglish
Pages (from-to)20874-20885
Number of pages12
JournalPhysical Chemistry Chemical Physics
Issue number32
Early online date24 Jul 2018
Publication statusPublished - 28 Aug 2018


Calculations were carried out on Galileo (CINECA: Casalecchio di Reno, Italy) thanks to the ISCRA Grant STREGA (Filling the STructure–REactivity GAp: in silico multiscale approaches to rationalize the design of molecular catalysts.), P. I.: L. O., M. D. T. is grateful to Fondazione CARIPARO for financial support (PhD grant), C. F. G. and F. M. B. thank the Netherlands Organisation for Scientific Research (NWO) for financial support.

FundersFunder number
Fondazione Cassa di Risparmio di Padova e Rovigo
Nederlandse Organisatie voor Wetenschappelijk Onderzoek


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