π Facial hydrogen bonding in the chiral resolving agent (S)-2,2,2-trifluoro-1-(9-anthryl)ethanol and its racemic modification

Abstract

Single crystal X-ray analysis reveals that although molecules of pure (S)-and racemic(R,S)-2,2,2-trifluoro-1-(9-anthryl)ethanol 1 differ significantly in their intermolecular packing; in each case a strong hydrogen bond is formed between the OH group of one molecule and a specific π-face of one benzo ring of 1 which PM3 derived molecular electrostatic potentials show to arise via stereoelectronic assistance from the OH group.