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]
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| Names | |||
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| Preferred IUPAC name
Tri-tert-butoxysilanethiol | |||
| Other names
Tri(tert-butoxy)silanethiol
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| Identifiers | |||
3D model (JSmol)
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| Abbreviations | TBST | ||
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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silanethiol.svg)
silanethiol.png)
- 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
edit- ^ 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.
- ^ 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.
- ^ J. Chojnacki: DFT and NBO theoretical study of protonation of tri-tert-butoxysilanethiol and its anion. Polyhedron 27(3) (2008) 969-976.
- ^ 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.
- ^ 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.
- ^ A. Dołęga: Alcohol dehydrogenase and its simple inorganic models. Coord. Chem. Rev. 254 (2010) 916-937.
- ^ 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.
- ^ 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.
- ^ 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.