tris(tert-butoxy)silanethiol

{{DISPLAYTITLE:Tris(tert-butoxy)silanethiol}}

{{Chembox

| Name = Tris(tert-butoxy)silanethiol

| ImageFileL1 = Tri(tert-butoxy)silanethiol.svg

| ImageNameL1 = Partially condensed structural formula of tris(tert-butoxy)silanethiol

| ImageFileR1 = Tri(tert-butoxy)silanethiol.png

| ImageNameR1 = Ball and stick model of tris(tert-butoxy)silanethiol

| PIN = Tri-tert-butoxysilanethiol

| OtherNames = Tri(tert-butoxy)silanethiol

|Section1={{Chembox Identifiers

| Abbreviations = TBST

| CASNo = 690-52-8

| CASNo_Ref = {{cascite|?|??}}

| PubChem = 5246420

| ChemSpiderID = 4414610

| ChemSpiderID_Ref = {{Chemspidercite|correct|ChemSpider}}

| SMILES = CC(C)(C)O[Si](S)(OC(C)(C)C)OC(C)(C)C

| StdInChI = 1S/C12H28O3SSi/c1-10(2,3)13-17(16,14-11(4,5)6)15-12(7,8)9/h16H,1-9H3

| StdInChIKey = ZVUGYOCGLCLJAV-UHFFFAOYSA-N}}

|Section2={{Chembox Properties

| C=12 | H=28 | O=3 | S=1 | Si=1

| Appearance = Colourless liquid

| BoilingPtC = 113 to 115

| BoilingPt_notes = at 35 mmHg}}

}}

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 a hydrogen donor in radical chain reactions. It was first prepared by alcoholysis of silicon disulfide and purified by distillation: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.

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

Since 1962 it was thoroughly studied including its acid-base propertiesW. 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. and coordination chemistry with metal ions. It coordinates to metal ions via the sulfur and oxygen donor atoms.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.