Ability ofB12N12fullerene like nano‐cage for sensing and improving the antioxidant activity of juglone and its derivative: Density functional theory investigation

Abstract Theoretical chemistry calculations were used to investigate the ability of the B 12 N 12 fullerene like nano‐cage for sensing juglone ( Jug ) and one of its derivative ( Jug  OH ) in gas phase, pentyl ethanoate (PE) and water. Results obtained at DFT/M05‐2X‐D3/6‐311+G(d,p) level of theory showed that B 12 N 12 is able to adsorbed Jug preferentially by binding to one of the O‐atom of its carbonyl groups. Based on natural bond orbital analysis, a charge transfer from the oxygen atoms of Jug and JugOH to the anti‐bonding orbital of B was revealed. Quantum theory of atoms in molecule analysis showed that the B 12 N 12 Jug and B 12 N 12 JugOH complexes are stabilized by a partially covalent BO bond in addition to attractive non covalent interactions. The ability of Jug , Jug  OH as well as their complexes A and AOH to scavenge HO ● radical has been investigated via the usual hydrogen atom transfer mechanism in the three media of study previously stated. Theoretical evaluation of pH effect on this radical scavenging activity revealed that in water, the anionic forms of Jug  OH (86%) and AOH (96%) are dominant and mainly transfer their remaining H‐atom to HO ● via a spontaneously reaction, the complex presenting the lowest Gibbs free energy. These results provide fundamental knowledge for the development of new antioxidant delivery careers.