19F NMR Study of the Halogen Bonding between Haloperfluorocarbons and Heteroatom Containing Hydrocarbons
J. Fluorine Chem. 2002, 114, 27
P. Metrangolo, W. Panzeri, F. Recupero, G. Resnati
Chemical shift differences (<i>Δ δ</i> <sub>CF</sub>)<sup>a</sup> of 1,4-diiodotetrafluorobenzene (<b>11</b>) and 1,4-dibromotetrafluorobenzene (<b>12</b>) in <i>n</i>-pentane and the given solvent.
Chemical shift differences (Δ δ CF)a of 1,4-diiodotetrafluorobenzene (11) and 1,4-dibromotetrafluorobenzene (12) in n-pentane and the given solvent.
ABSTRACT
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 hydrocarbon modules to take part in the formation of halogen bonds.