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Helical structure of tercyclopropanedimethanol in solution.

Anthony G M Barrett1, Rachel A James, Gillian E Morton

  • 1Department of Chemistry, Imperial College, South Kensington, London SW7 2AY, United Kingdom. agmb@ic.ac.uk

The Journal of Organic Chemistry
|March 25, 2006
PubMed
Summary

Researchers studied the helical conformation of oligocyclopropanes using NMR and DFT. They found a dominant helical structure in tercyclopropanedimethanol, aligning with some crystal data but differing from others.

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Area of Science:

  • Organic Chemistry
  • Structural Chemistry
  • Natural Products Chemistry

Background:

  • Oligocyclopropanes are natural products with repetitive stereochemistry and bioactivity.
  • Existing X-ray crystal structures show partially contradictory results for these compounds.
  • NMR spectra of oligocyclopropanes are complex and challenging to assign.

Purpose of the Study:

  • To determine the conformation of oligocyclopropanes in solution.
  • To resolve discrepancies between existing crystal structure data.
  • To characterize the helical conformation of tercyclopropanedimethanol.

Main Methods:

  • Preparation of a specifically deuterated sample of tercyclopropanedimethanol.
  • High-field Nuclear Magnetic Resonance (NMR) spectroscopy.

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  • Density Functional Theory (DFT) calculations.

    • Main Results:

    • A helical conformation with equal handedness was identified for tercyclopropanedimethanol in solution.
    • A dihedral angle of approximately +40 degrees best represents the experimental data.
    • This solution structure is in agreement with the crystal structure of quinquecyclopropanedimethanol but differs from the crystal structure of the title compound.

    Conclusions:

    • The dominating conformation of tercyclopropanedimethanol in solution is helical, characterized by a repetitive (+)-gauche interunit dihedral angle.
    • Solution and crystal structures can differ for oligocyclopropanes.
    • High-field NMR and DFT calculations are effective tools for elucidating complex molecular conformations.