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

Zackaria Nairoukh*, Felix Strieth-Kalthoff, Klaus Bergander, Frank Glorius

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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.

Original languageAmerican English
Pages (from-to)6141-6146
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number28
DOIs
StatePublished - 15 May 2020
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • NMR analysis
  • conformational behavior
  • fluorine
  • piperidines
  • solvation effect

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