Abstract
Conformational preferences of substituted, saturated cyclic ketones (piperidones and cyclohexanones) may deviate from those of their oxygenless analogues. 1-Phenylpiperidin-4-one was found to exist in several forms differing by not only position (axial or equatorial) of the aryl-substituent but also by a configuration of the piperidine cycle itself: chair-Eq, chair-Ax and twist (Tw). The ratios of the co-existing species contributions in gas phase predicted by various quantum chemical calculations were confirmed by synchronous gas-phase electron diffraction and mass spectrometric experiments carried out for the vapor at 337 K demonstrating a best fit with the B3LYP-D3/cc-pVTZ combination: Eq:Ax:Tw = 55(13):22(9):23(10) vs. 40:35:25.
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