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Related Concept Videos

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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tert-Butoxy-triphenyl-silane.

Jonathan O Bauer1, Carsten Strohmann

  • 1Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of triphenyl-tert-butoxysilane (Ph(3)SiO(t)Bu), revealing a distorted tetrahedral silicon center. The findings offer insights into sterically hindered silicon compounds relevant to organosilicon chemistry.

Area of Science:

  • Organosilicon Chemistry
  • Crystallography
  • Materials Science

Background:

  • Organosilicon compounds, featuring R(3)SiO motifs, are broadly applicable across various chemical disciplines.
  • Understanding the structural and electronic properties of silicon centers with bulky substituents is crucial for designing novel materials and catalysts.

Purpose of the Study:

  • To elucidate the detailed crystal structure of triphenyl-tert-butoxysilane (Ph(3)SiO(t)Bu).
  • To analyze the coordination geometry and intermolecular interactions within the title compound.
  • To establish Ph(3)SiO(t)Bu as a model system for sterically demanding silicon centers.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Geometric parameters, including bond angles (C-O-Si) and bond lengths (O-Si), were precisely measured.

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  • Intermolecular interactions, specifically hydrogen-hydrogen distances, were analyzed to understand crystal packing.
  • Main Results:

    • The silicon atom in Ph(3)SiO(t)Bu exhibits a distorted tetrahedral coordination sphere.
    • The C-O-Si angle was determined to be 135.97(12)°, and the O-Si distance was 1.6244(13) Å.
    • The shortest intermolecular distance observed was an H⋯H interaction of 2.2924(7) Å between aryl hydrogen atoms, indicating weak inter-unit forces.

    Conclusions:

    • Ph(3)SiO(t)Bu serves as a valuable model compound for studying silicon centers with significant steric bulk.
    • The structural data provides fundamental insights into the behavior of R(3)SiO motifs in solid-state chemistry.
    • This research contributes to the broader understanding of organosilicon structures and their potential applications.