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Electrostatic CH-π Interactions Can Override Fluorine Gauche Effects To Exert Conformational Control.

Bright U Emenike1, Amiel Farshadmand1, Matthias Zeller2

  • 1Department of Chemistry & Physics, State University of New York, Old Westbury, 223 Store Hill Road, Old Westbury, NY 11568, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
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PubMed
Summary

The physical origins of fluorine gauche effects are clarified by intramolecular CH⋅⋅⋅π aromatic interactions. These through-space interactions, influenced by substituents, impact molecular conformation, challenging existing theories.

Keywords:
Hammett constantsaromatic interactionscoupling constantsgauche effects

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Fluorine gauche effects in 2-fluoroethanes are crucial in molecular design but their physical origins remain debated.
  • Current consensus favors hyperconjugation theory, overlooking potential electrostatic contributions.

Purpose of the Study:

  • To investigate the role of intramolecular CH⋅⋅⋅π aromatic interactions in fluorine gauche effects.
  • To explore the electrostatic nature of these through-space interactions and their influence on molecular conformation.

Main Methods:

  • Utilized a series of model systems to study fluorine gauche effects.
  • Employed proton NMR spectroscopy for experimental analysis.
  • Performed gas-phase Density Functional Theory (DFT) calculations and solid-state X-ray crystallography for corroboration.

Main Results:

  • Demonstrated that intramolecular CH⋅⋅⋅π aromatic interactions can influence the preference for fluorine gauche effects.
  • Showcased that modulating the aromatic ring with substituents (e.g., nitro, amine) alters the CH⋅⋅⋅π interaction strength.
  • Observed a linear Hammett relationship, indicating electrostatic characteristics of the CH⋅⋅⋅π interaction.

Conclusions:

  • Intramolecular CH⋅⋅⋅π aromatic interactions play a significant role in governing fluorine gauche effects.
  • The electrostatic nature of CH⋅⋅⋅π interactions provides a new perspective on conformational preferences in fluorinated compounds.
  • Findings challenge the sole reliance on hyperconjugation theory and highlight the importance of through-space interactions.