Abstract
Abstract13C NMR spectra of six epimeric substituted 4‐hydroxypiperidines and two corresponding piperidines were recorded. Substituent parameters for equatorial methyl, gem‐dimethyl, equatorial hydroxy and axial hydroxy groups were calculated from the 13C chemical shifts of these compounds and several other six‐membered ring compounds. The effects of nearby substituents on these parameters were examined. It is concluded that the magnitude and even the sign of the α effect is modified by the presence of nearby substituents. It was found that gauche interactions play an important role in determining the magnitude of the α effect. However, the β effect is not influenced by the nearby substituents except for the gem‐dimethyl group. The magnitude of the γ effect is almost independent of the nearby substituents.
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