Reduction of hydrogen peroxide by amine-based diselenides: understanding the effect of substitutions on reactivity

Abstract

Many small organoselenium compounds, such as substituted diselenides, mimic the glutathione peroxidase (GPx) activity by catalysing the reduction of hydrogen peroxide. In this context, the effect of substitution in di-2(N-cyclohexyl,N-(methylamino)-methyl)phenyl diselenide (CMP) on its GPx-like activity (to reduce hydrogen peroxide) has been investigated using the density functional theory. It was observed that the presence of an electron donating group as well as secondary amino group (instead of tertiary one) favoured the peroxide reduction process, which is consistent with the experimental reports. This study revealed that the presence of electron donating group lowers the energy requirement for distortion in zwitterion of the selenol during the progress of the reaction, thereby enhancing its catalytic activity.