Magnetic resonance and mass spectrometric characterization and conformational analysis of α,α-bis(4-fluorophenyl)-β-methyl-1H-imidazole-1-ethanol

Abstract

A complete multinuclear magnetic resonance characterization of α,α-bis(4-fluorophenyl)-β-methyl-1H-imidazole-1-ethanol (a representative carbinoloimidazole topical anti-inflammatory agent) is presented, the first such assignment of a compound with diastereotopic fluorophenyl rings. The relative orientation of the 4-fluorophenyl rings was probed experimentally by 1H nuclear Overhauser effect spectroscopy experiments; these confirm the results of a density functional theory based optimization of the structure, in which the phenyl rings are oriented to avoid coplanarity. High resolution time-of-flight mass spectrometry confirmed the structure of the molecule.