Exploring the simultaneous σ-hole/π-hole bonding characteristics of a Br...π interaction in an ebselen derivative <i>via</i> experimental and theoretical electron-density analysis

Abstract

In this study, the nature and characteristics of a short Br⋯π interaction observed in an ebselen derivative, 2-(2-bromophenyl)benzo[<i>d</i>][1,2]selenazol-3(2<i>H</i>)-one, has been explored. The electronic nature of this Br⋯π interaction was investigated <i>via</i> high-resolution X-ray diffraction and periodic density functional theory calculations using atoms-in-molecules (AIM) analysis. This study unravels the simultaneous presence of σ-hole and π-hole bonding characteristics in the same interaction. The dual characteristics of this unique Br⋯π interaction are further established <i>via</i> molecular electrostatic potentials (MESPs) and natural bond orbitals (NBOs).