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Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial-F Preference.


ABSTRACT: Gaining an understanding of the conformational behavior of fluorinated compounds would allow for expansion of the current molecular design toolbox. In order to facilitate drug discovery efforts, a systematic survey of a series of diversely substituted and protected fluorinated piperidine derivatives has been carried out using NMR spectroscopy. Computational investigations reveal that, in addition to established delocalization forces such as charge-dipole interactions and hyperconjugation, solvation and solvent polarity play a major role. This work codifies a new design principle for conformationally rigid molecular scaffolds.

SUBMITTER: Nairoukh Z 

PROVIDER: S-EPMC7317880 | biostudies-literature |

REPOSITORIES: biostudies-literature

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