Investigation of C–F···F–C Interactions Using Experimental and Theoretical Charge Density Analyses
Labhini Singla, Anil Kumar, Craig M. Robertson, Parthapratim Munshi, Angshuman Roy Choudhury
Abstract
Among the halogens, fluorine plays a crucial role in governing the potency of drugs and pharmaceuticals. In this study, experimental and theoretical charge density analyses have been performed on N-(2,5-difluorophenyl)-3,5-difluoro-N-(3-methoxyphenethyl)benzamide to study the nature of weak intermolecular interactions, especially the F···F interactions, mediated by organic fluorine. The kind of C–F···F–C interactions analyzed in this study are Type I and quasi Type I/Type II. For this, the quantitative and qualitative analyses of electron densities have been performed based on the multipole modeling of high-resolution experimental X-ray diffraction data and theoretical structure factors generated from periodic calculations. The interactions have been analyzed based on the topological properties of electron densities using quantum theory of atoms in molecules (QTAIM). Thus, the nature of organic fluorine has been investigated by studying deformation of electron densities, Laplacian, and topological parameters.