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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Origami with small molecules: exploiting the C-F bond as a conformational tool.

Patrick Ryan1, Ramsha Iftikhar1, Luke Hunter1

  • 1School of Chemistry, The University of New South Wales (UNSW), Sydney 2052, Australia.

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|April 8, 2025
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Summary

Fluorine's C-F bond influences molecular shape through stereoelectronic effects. This review covers 2010-2024 developments in using these effects to enhance functional molecules like pharmaceuticals and liquid crystals.

Keywords:
conformational analysismedicinal chemistryorganofluorine chemistrystereoselective fluorination

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Area of Science:

  • Organic Chemistry
  • Molecular Conformation
  • Fluorine Chemistry

Background:

  • The carbon-fluorine (C-F) bond exhibits predictable alignment with neighboring functional groups.
  • Stereoelectronic effects, including hyperconjugation and electrostatic interactions, drive these conformational preferences.

Purpose of the Study:

  • To review the advancements in exploiting fluorine-derived conformational effects.
  • To highlight the impact of these effects on molecular properties and applications from 2010-2024.

Main Methods:

  • Literature review of scientific publications from 2010-2024.
  • Analysis of studies demonstrating the application of C-F bond conformational control.

Main Results:

  • Fluorine's influence on molecular conformation is a key factor in designing functional molecules.
  • These effects have been successfully applied to optimize pharmaceuticals, liquid crystals, fragrances, organocatalysts, and peptides.

Conclusions:

  • Stereoelectronic effects of the C-F bond offer a powerful tool for molecular engineering.
  • Continued research in this area promises further innovation in materials science and drug discovery.