Tris(tert-butoxy)silanethiol explained

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.