Jump to content

Tris(tert-butoxy)silanethiol

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Yobot (talk | contribs) at 12:44, 29 March 2018 (Removed invisible unicode characters + other fixes (Task 55), removed: ­ (2) using AWB (12151)). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Tris(tert-butoxy)silanethiol
Partially condensed structural formula of tris(tert-butoxy)silanethiol
Partially condensed structural formula of tris(tert-butoxy)silanethiol
Ball and stick model of tris(tert-butoxy)silanethiol
Ball and stick model of tris(tert-butoxy)silanethiol
Names
IUPAC name
Tris(tert-butoxy)silanethiol
Other names
Tri(tert-butoxy)silanethiol
Identifiers
3D model (JSmol)
Abbreviations TBST
ChemSpider
  • 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
Appearance Colourless 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).

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]

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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tris(tert-butoxy)silanethiol&oldid=833056603"