Geometries and conformational processes in phencyclidine and a rigid adamantyl analogue: variable-temperature NMR, X-ray crystallographic, and molecular mechanics studies.
The barriers to rotation of the aryl groups of m-nitrophenyladamantylpiperidine and m-nitrophenylcyclohexylpiperidine have been studied by variable-temperature NMR spectroscopy. NMR spectra of the free bases and salts of phenyladamantylpiperidine and phenylcyclohexylpiperidine (phencyclidine) and an X-ray crystal structure of the adamantane derivative verify the preferred conformations of these molecules in solution and the solid state. Force-field calculations provide additional information on the energetics of conformational processes in these molecules.
D000218:Adamantane / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010622:Phencyclidine / Q000031:analogs & derivatives*; D013696:Temperature; D014961:X-Ray Diffraction; D014965:X-Rays
C037811:phenyladamantylpiperidine; D010622:Phencyclidine; D000218:Adamantane