Conformations of N,N-Bis(2-fluorophenyl)carbamoyl Chloride

Article abstract of DOI:10.1021/jo00278a017

The structure of the title compounds has been examined by X-ray crystallographic and fluorine NMR methods.In the solid state the planes of the fluorophenyl rings are oriented at angles of 98 deg and 64 deg relative to the plane through the atoms of the carbamoyl chloride group.Fluorine NMR studies indicate that the conformational properties of the molecule in solution are similar to this.Fluorine NMR lineshape data were used to estimate the rates of roation of the fluorophenyl rings and the rate of rotation about the carbamoyl nitrogen-carbon bond.Observation of a large fluorine-fluorine coupling constant, likely the result of a through-space interaction, supports the conclusions regarding the conformations of this compound in solution.