Tris(tert-butoxy)silanethiol

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Tris(tert-butoxy)silanethiol
Partially condensed structural formula of tris(tert-butoxy)silanethiol Tri(tert-butoxy)silanethiol.svg
Partially condensed structural formula of tris(tert-butoxy)silanethiol
Ball and stick model of tris(tert-butoxy)silanethiol Tri(tert-butoxy)silanethiol.png
Ball and stick model of tris(tert-butoxy)silanethiol
Names
Preferred IUPAC name
Tri-tert-butoxysilanethiol
Other names
Tri(tert-butoxy)silanethiol
Identifiers
3D model (JSmol)
AbbreviationsTBST
ChemSpider
PubChem CID
  • InChI=1S/C12H28O3SSi/c1-10(2,3)13-17(16,14-11(4,5)6)15-12(7,8)9/h16H,1-9H3
    Key: ZVUGYOCGLCLJAV-UHFFFAOYSA-N
  • CC(C)(C)O[Si](S)(OC(C)(C)C)OC(C)(C)C
Properties
C12H28O3SSi
Molar mass 280.50 g·mol−1
AppearanceColourless liquid
Boiling point 113 to 115 °C (235 to 239 °F; 386 to 388 K)at 35 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tris(tert-butoxy)silanethiol is a silicon compound containing three tert-butoxy groups and a rare Si–S–H functional group. This colourless compound serves as an hydrogen donor in radical chain reactions. It was first prepared by alcoholysis of silicon disulfide and purified by distillation: [1]

3 (CH3)3COH + SiS2 → [(CH3)3CO]3SiSH + H2S

Since 1962 it was thoroughly studied including its acid-base properties [2] [3] and coordination chemistry with metal ions. It coordinates to metal ions via the sulfur and oxygen donor atoms. [4] [5] [6] [7] [8] [9]

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Platinum(II) chloride

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Silicon disulfide

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Manganese(IV) fluoride

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Copper(I) fluoride

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3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR′). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

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Phosphasilene

Phosphasilenes or silylidenephosphanes are a class of compounds with silicon-phosphorus double bonds. Since the electronegativity of phosphorus (2.1) is higher than that of silicon (1.9), the "Si=P" moiety of phosphasilene is polarized. The degree of polarization can be tuned by altering the coordination numbers of the Si and P centers, or by modifying the electronic properties of the substituents. The phosphasilene Si=P double bond is highly reactive, yet with the choice of proper substituents, it can be stabilized via donor-acceptor interaction or by steric congestion.

Hexa(tert-butoxy)ditungsten(III)

Hexa(tert-butoxy)ditungsten(III) is a coordination complex of tungsten(III). It is one of the homoleptic alkoxides of tungsten. A red, air-sensitive solid, the complex has attracted academic attention as the precursor to many organotungsten derivatives. It an example of a charge-neutral complex featuring a W≡W bond, arising from the coupling of a pair of d3 metal centers. It has attracted particular attention for its reactions with alkynes, leading to alkyne metathesis.

References

  1. R. Piękoś, W. Wojnowski: Untersuchungen über die Alkoholyse des SiS2. II. Darstellung von Trialkoxysilanthiolen und Tetraalkoxycyclodisilthianen aus den tertiären Alkoholen. Z. anorg. allg. Chem. 318 (1962) 212-216.
  2. W. Wojnowski, A. Herman: Beiträge zur Chemie der Silicium-Schwefel-Verbindungen. XX. Die Dissoziation der Silanthiole in wäßriger Lösung. Z. anorg. allg. Chem. 425 (1976) 91-96.
  3. J. Chojnacki: DFT and NBO theoretical study of protonation of tri-tert-butoxysilanethiol and its anion. Polyhedron 27(3) (2008) 969-976.
  4. A. Dołęga, K. Baranowska, D. Gudat, A. Herman, J. Stangret, A. Konitz, M. Śmiechowski, S. Godlewska: Modeling of the Alcohol Dehydrogenase Active Site: Two Different Modes of Alcohol Binding in Crystals of Zinc and Cadmium Tri-tert-butoxysilanethiolates Evidenced by X-ray Diffraction and Solid-State Vibrational Spectroscopy. Eur. J. Inorg. Chem. (2009) 3644-3660.
  5. A. Dołęga, A. Farmas, K. Baranowska, A. Herman: Novel zinc complexes with acetyloacetonate, imidazole and thiolate ligands. Crystal structure of a zinc complex of relevance to farnesyl transferase. Inorg. Chem. Comm. 12 (2009) 823-827.
  6. A. Dołęga: Alcohol dehydrogenase and its simple inorganic models. Coord. Chem. Rev. 254 (2010) 916-937.
  7. A. Pladzyk, Ł. Ponikiewski, Y. Lan, A. K. Powell: Synthesis, structure and magnetic properties of neutral Ni (II) tri-tert-butoxysilanethiolate cluster. Inorg. Chem. Comm. 20 (2012) 66-69.
  8. A. Pladzyk, Z. Hnatejko, K. Baranowska: Binuclear Co(II), Zn(II) and Cd(II) tri-tert-butoxysilanethiolates. Synthesis, crystal structure and spectroscopic studies. Polyhedron 79 (2014) 116-123.
  9. A. Pladzyk, A. Ozarowski, Ł. Ponikiewski: Crystal and electronic structures of Ni(II) silanethiolates containing flexible diamine ligands. Inorg. Chim. Acta 440 (2016) 84-93.