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Sterically congested in-methylcyclophanes.

Qiuling Song1, Douglas M Ho, Robert A Pascal

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|August 11, 2005
PubMed
Summary
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Researchers synthesized a highly congested cyclophane, revealing unprecedentedly close contacts between methyl groups and aromatic rings. This structural compression significantly shortens carbon-methyl bonds, offering new insights into strained molecular architectures.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Cyclophanes are cyclic organic compounds known for their unique structural properties.
  • Steric congestion in cyclophanes can lead to unusual bond lengths and spatial arrangements.
  • Triptycene derivatives offer a rigid framework for constructing complex molecular architectures.

Purpose of the Study:

  • To synthesize a novel, highly congested in-methylcyclophane.
  • To investigate the structural consequences of extreme steric crowding in cyclophanes.
  • To determine the precise molecular geometry and bonding characteristics of the synthesized compound.

Main Methods:

  • Synthesis of cyclophane 9 via condensation under high dilution conditions.
  • Oxidation of cyclophane 9 to the corresponding trisulfone 10.

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  • X-ray crystallography for detailed structural determination of trisulfone 10.

    • Main Results:

    • Successful synthesis of the highly congested in-methylcyclophane 9 and its trisulfone derivative 10.
    • X-ray structure determination revealed exceptionally short contacts (2.87-2.90 Å) between in-methyl carbons and the aromatic ring centroid.
    • Observed significant compression of C-CH3 bonds (1.475-1.495 Å) compared to unstrained analogues (ca. 1.54 Å).

    Conclusions:

    • The synthesized cyclophane exhibits the closest ever observed contacts between methyl groups and aromatic systems.
    • Extreme steric congestion demonstrably compresses C-CH3 bonds, altering their intrinsic lengths.
    • This study provides valuable experimental data on the limits of molecular packing and strain in organic molecules.