Nortropacocaine hydrochloride conformation in aqueous and hydrophobic media.
The nortropacocaine hydrochloride PMR spectra in deuterium oxide and in deuterochloroform differed markedly. A detailed conformational analysis using vicinal 1H-1H coupling constants revealed the molecular conformation to be identical in both solvents. The preferred conformation was one in which the piperidine component existed as a deformed chair. The spectral differences were due to a decreased deshielding of the protonated nitrogen on the neighboring bicyclic ring protons, resulting in chemical shift changes.
D002725:Chloroform; D003042:Cocaine / Q000031:analogs & derivatives*; D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012997:Solvents; D014867:Water
D012997:Solvents; D014867:Water; C020437:nortropacocaine; D002725:Chloroform; D003903:Deuterium; D003042:Cocaine