Exploring the simultaneous σ-hole/π-hole bonding characteristics of a Br...π interaction in an ebselen derivative via 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[d][1,2]selenazol-3(2H)-one, has been explored. The electronic nature of this Br...π interaction was investigated via 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 via molecular electrostatic potentials (MESPs) and natural bond orbitals (NBOs).

Keywords

• σ-hole bonding
• π-hole bonding
• ebselen
• electron density
• molecular electrostatic potentials
• crystal engineering
• charge, spin and momentum densities
• computational modelling
• molecular crystals