Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 28, Pages 6141-6146Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001355
Keywords
conformational behavior; fluorine; NMR analysis; piperidines; solvation effect
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Funding
- European Research Council (ERC) [788558]
- Deutsche Forschungsgemeinschaft [SPP2102]
- European Research Council (ERC) [788558] Funding Source: European Research Council (ERC)
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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.
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