The NH---FC Dipole Orientation Effect for Pendant Exocyclic CH₂F

Abstract

[structure: see text] DFT and MMFF force field calculations for 2 (R = H) predict that two conformers dominate in water (>/=95%) and both sustain a geometry in which the C-F and H-N dipoles align oppositely in a near-planar arrangement. The (1)H NMR spectra (D(2)O and DMSO-d(6)) and X-ray structure for 2 (R = SO(2)NHEt) confirm the predictions in all essentials. A novel single-conformer system is proposed.