The conformational preferences of 2-fluoro and 2-trifluoromethylpiperidine have been investigated with a variety of computational approaches including molecular mechanics, density functional theory, and post-HF ab initio methods. Conformations with the fluoro or trifluoromethyl group axial are found to be stabilized in a manner consistent with a stereoelectronic effect akin to the anomeric effect.  Results from a variety of levels of theory including ?B97XD, B2PLYP-D, and CCSD(T) will be compared.  Natural bond orbital analysis will be used to provide insight into the conformer relative stabilities.  The impact of the stereoelectronic effect on the ability of the X-C-N (X =F, CF3) moiety to engage in intermolecular hydrogen bonding interactions will also be investigated.

Anomeric effects in fluoro and trifluoromethylpiperidines

243rd National Meeting (2012)

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