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 (R-f-X, R-f = aliphatic or aromatic perfluorinated residue, X = 1, Br, Cl) and heteroatom containing hydrocarbons (HC-D, HC = hydrocarbon residue, D = electron donor heteroatom) results in the formation of R-f-(XD)-D-...-HC complexes in the liquid phase. This formation strongly affects the F-19 NMR spectra of the perfluorinated partners. The Deltadelta(-CF2X),X and the Deltadelta(-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. (C) 2002 Elsevier Science B.V. All rights reserved.