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Dicubyl disulfide.

Ronny Priefer1, Yoon Joo Lee, Fabiola Barrios

  • 1Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.

Journal of the American Chemical Society
|May 16, 2002
PubMed
Summary
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Researchers synthesized dicubyl disulfide, a novel sulfur compound. X-ray crystallography revealed a record-short carbon-sulfur bond, and computational and NMR studies confirmed a low sulfur-sulfur bond rotation barrier.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Cubane derivatives are known for their unique structural properties.
  • Sulfur-containing organic molecules exhibit diverse chemical behaviors.
  • Understanding bond characteristics in strained systems is crucial for chemical synthesis.

Purpose of the Study:

  • To synthesize and characterize dicubyl disulfide.
  • To investigate the C-S and S-S bond properties in this novel cubane derivative.
  • To compare experimental findings with theoretical predictions.

Main Methods:

  • Multi-step organic synthesis starting from dimethyl-1,4-cubanedicarboxylate.
  • X-ray crystallography for structural determination.
  • Density functional theory (DFT) calculations for electronic structure.

Related Experiment Videos

  • Low-temperature Carbon-13 Nuclear Magnetic Resonance (NMR) spectroscopy.

    • Main Results:

    • Dicubyl disulfide was synthesized in 47% overall yield through a six-step process.
    • X-ray crystallography identified the shortest tetragonal carbon-sulfur bond (1.771 Å).
    • DFT calculations and low-temperature NMR confirmed a low sulfur-sulfur bond rotation barrier.

    Conclusions:

    • The synthesis of dicubyl disulfide expands the scope of cubane chemistry.
    • The observed C-S bond length challenges previous assumptions about bond characteristics in strained systems.
    • The low S-S rotation barrier provides new insights into the conformational flexibility of sulfur compounds.