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Monomeric siliconthiodichloride trapped by a Lewis base.

Sudipta Roy1, Kartik Chandra Mondal1, Totan Mondal2

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Researchers synthesized and characterized the first stable monomeric siliconthiodichloride, stabilized by a cyclic alkyl(amino) carbene (cAAC). This breakthrough in silicon chemistry offers new possibilities for organic synthesis and materials science.

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Area of Science:

  • Inorganic Chemistry
  • Organosilicon Chemistry
  • Carbene Chemistry

Background:

  • Thiophosgene (CSCl2) is a monomeric reagent used in organic synthesis.
  • Siliconthiodichloride (SiSCl2), its heavier analogue, has only been isolated as a dimer or tetramer.
  • Stabilization of reactive silicon compounds is crucial for their application.

Purpose of the Study:

  • To synthesize and characterize the first neutral monomeric siliconthiodichloride.
  • To explore the stabilization of siliconthiodichloride using cyclic alkyl(amino) carbenes (cAACs).
  • To investigate the properties and structure of the novel monomeric siliconthiodichloride.

Main Methods:

  • Synthesis of (cAAC)SiSCl2 via reaction of silylenes with elemental sulfur (S8).
  • Isolation and characterization using X-ray single crystal diffraction, NMR, UV-vis, and IR spectroscopy.
  • Theoretical calculations to study bonding and electron density distributions.

Main Results:

  • Successfully synthesized and isolated the monomeric cyclic alkyl(amino) carbene-stabilized siliconthiodichloride, (cAAC)SiSCl2.
  • The compound is a bright yellow solid, soluble in polar organic solvents, and stable at room temperature for a month.
  • X-ray diffraction confirmed the monomeric molecular structure, and spectroscopic data supported its characterization.

Conclusions:

  • The first stable monomeric siliconthiodichloride has been synthesized and characterized.
  • Cyclic alkyl(amino) carbenes effectively stabilize siliconthiodichloride, enabling isolation in its monomeric form.
  • This work opens new avenues for the chemistry and application of silicon-sulfur compounds.