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The NH---FC dipole orientation effect for pendant exocyclic CH(2)F
David C Lankin1, Gary L Grunewald, F Anthony Romero
1Pharmacia Corporation, 4901 Searle Parkway/P-024, Skokie, Illinois 60077, USA.
Organic Letters
|October 12, 2002
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.