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Related Experiment Videos

The Anomeric Effect: It's Complicated.

Kenneth B Wiberg1, William F Bailey2, Kyle M Lambert2

  • 1Department of Chemistry , Yale University , 275 Prospect Street , New Haven , Connecticut 06520-8107 , United States.

The Journal of Organic Chemistry
|April 6, 2018
PubMed
Summary

The anomeric effect, a key chemical phenomenon, arises from multiple interactions, not a single cause. Stabilizing Coulombic attractions between hydrogen and polar substituents are the primary drivers.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • The anomeric effect describes the conformational preference of substituents in cyclic systems.
  • Understanding its origin is crucial for predicting molecular behavior and designing new compounds.

Purpose of the Study:

  • To reexamine the origin of the anomeric effect through integrated experimental and computational methods.
  • To identify and quantify the specific interactions responsible for the axial preference.

Main Methods:

  • Coordinated experimental investigations.
  • Computational modeling and analysis.

Main Results:

  • Multiple, correlated interactions contribute to the anomeric effect.

Related Experiment Videos

  • CH···G nonbonded Coulombic attractions between axial substituents and ring hydrogens are experimentally demonstrated.
  • Hyperconjugation is a minor contributor; charge transfer primarily occurs within the H-C-G unit.

    • Conclusions:

    • No single factor uniquely explains the anomeric effect.
    • The anomeric effect predominantly originates from CH···G nonbonded Coulombic attractions.
    • Bond lengthening and favorable Coulombic interactions stabilize the axial conformation.