Abstract
13C chemical shifts of compounds of type EC XY (E = O, S; X, Y = F, Cl, Br, SCF 3 and SeCF 2) and 19F chemical shifts and coupling constants 1J(CF) of the fluorine containing compounds are reported. The NMR data of these sp 2-carbon compounds are compared with those of type ECF 3 containing sp 3-carbon. The chemical shifts of the compounds EC XY are interpreted in terms of halogen—carbon π bonding. These bondings are stronger in fluorine than in chlorine and bromine compounds. The coupling constant 1J(CF) increases in magnitude with increasing s-character of the carbon atom in compounds with E = O, S and Se. An extremely large value of 408 Hz is found in SeCF 2. Evidence for considerable noncontact contribution to 1J(CF) is derived from the data. Furthermore 1J(CF) values are related to CF stretching force constants.
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