Perfluorocarbon–hydrocarbon self-assembly: Part 16. 19F NMR study of the halogen bonding between halo-perfluorocarbons and heteroatom containing hydrocarbons

The halogen bonding between structurally different halo-perfluorocarbons (Rf–X, Rf=aliphatic or aromatic perfluorinated residue, X=I, Br, Cl) and heteroatom containing hydrocarbons (HC–D, HC=hydrocarbon residue, D=electron donor heteroatom) results in the formation of Rf–X⋯D–HC complexes in the liquid phase. This formation strongly affects the 19F NMR spectra of the perfluorinated partners. The Δδ–CF2X and the Δδ–CFCX– values of perfluoroalkyl and aryl derivatives is proven to be a simple, powerful, and versatile tool to rank the tendency of perfluorocarbon and HC modules to be involved in halogen bonding formation.