Characterization of Interactions Involving Bromine in 2,2-Dibromo-2,3-dihydroinden-1-one via Experimental Charge Density Analysis

Abstract

Experimental and theoretical charge density analyses on 2,2-dibromo-2,3-dihydroinden-1-one have been carried out to quantify the topological features of a short C–Br···O halogen bond with nearly linear geometry (2.922 Å, ∠C–Br···O = 172.7°) and to assess the strength of the interactions using the topological features of the electron density. The electrostatic potential map indicates the presence of the “σ-hole” on bromine, while the interaction energy is comparable to that of a moderate O–H···O hydrogen bond. In addition, the energetic contribution of C–H···Br interaction is demonstrated to be on par with that of the C–Br···O halogen bond in stabilizing the crystal structure.