Organosilanols can be obtained by hydrolysis of organohalosilanes, such as chlorotrimethylsilane. They can also be prepared by the oxidation of organosilanes with oxidizing agents (R = organic residue):
The hydrolysis of silyl ethers generally proceeds only slowly:[4]
Hydrolysis of organosilanes is a first-order reaction. The hydrolysis rate of the Si-H bond depends on the type and number of organic residues. Thus, the hydrolysis rate of trialkylsilanes is significantly slower than that of triarylsilanes. This can be explained by a stronger increase in electron density on the silicon atom by the alkyl groups. Correspondingly, the reaction rate of the tri-n-alkylsilanes decreases in the series of ethyl, propyl, butyl groups. Trialkylsilanes with n-alkyl residues react by a factor of 10 faster than the analogous silanes with branched alkyl residues.[5]
Classificationedit
Depending on the substitution pattern of the silicon atom, a further distinction can be made. Organosilanols are classified as:
organosilanetriols, when three hydroxy groups and an organic residue are bound to a silicon atom, e. g. methylsilanetriol, phenylsilanetriol
organosilandiols, when two hydroxy groups and two organic residues are bound to a silicon atom, e. g. dimethylsilanediol, diphenylsilanediol
organosilanols, when one hydroxy group and three organic residues are bound to a silicon atom, e. g. trimethylsilanol, triethylsilanol or triphenylsilanol.
^Paul D. Lickiss (1995), "The synthesis and structure of organosilanols", Advances in Inorganic Chemistry, vol. 42, pp. 147–262, doi:10.1016/S0898-8838(08)60053-7
^Rudolf Pietschnig, Stefan Spirk (2016), "The Chemistry of Organo Silanetriols", Coordination Chemistry Reviews, vol. 323, pp. 87–106, doi:10.1016/j.ccr.2016.03.010
^ abBarry Arkles. "Silanes" (pdf). Gelest. p. 50. Retrieved 2016-12-10.
^G. Schott, C. Harzdorf (October 1960), "Silane. I Alkalische Solvolyse von Triorganosilanen", Zeitschrift für anorganische und allgemeine Chemie (in German), vol. 306, no. 3–4, pp. 180–190, doi:10.1002/zaac.19603060306
Wikimedia Commons has media related to Organosilanole.
April 13, 2024
organosilanols, organosilicon, chemistry, organosilanols, group, chemical, compounds, derived, from, silicon, more, specifically, they, carbosilanes, derived, with, hydroxy, group, silicon, atom, silicon, analogs, alcohols, silanols, more, acidic, more, basic,. In organosilicon chemistry organosilanols are a group of chemical compounds derived from silicon More specifically they are carbosilanes derived with a hydroxy group OH on the silicon atom 1 Organosilanols are the silicon analogs to alcohols Silanols are more acidic and more basic than their alcohol counterparts and therefore show a rich structural chemistry characterized by hydrogen bonding networks which are particularly well studied for silanetriols 2 3 Structure of trimethylsilanol Preparation editOrganosilanols can be obtained by hydrolysis of organohalosilanes such as chlorotrimethylsilane They can also be prepared by the oxidation of organosilanes with oxidizing agents R organic residue R2SiCl2 2HgO toluene 80 CR2Si OH 2 2Hg0 displaystyle ce R2SiCl2 2HgO gt 80 circ C toluene R2Si OH 2 2Hg 0 nbsp or by hydrolysis in the alkaline 4 H3C 3SiCl H2O H3C 3SiOH HCl displaystyle ce H3C 3SiCl H2O gt H3C 3SiOH HCl nbsp R3SiH H2O R3SiOH H2 displaystyle ce R3SiH H2O gt R3SiOH H2 nbsp The hydrolysis of silyl ethers generally proceeds only slowly 4 H5C2 3SiOC2H5 H2O H5C2 3SiOH HOC2H5 displaystyle ce H5C2 3SiOC2H5 H2O gt H5C2 3SiOH HOC2H5 nbsp Hydrolysis of organosilanes is a first order reaction The hydrolysis rate of the Si H bond depends on the type and number of organic residues Thus the hydrolysis rate of trialkylsilanes is significantly slower than that of triarylsilanes This can be explained by a stronger increase in electron density on the silicon atom by the alkyl groups Correspondingly the reaction rate of the tri n alkylsilanes decreases in the series of ethyl propyl butyl groups Trialkylsilanes with n alkyl residues react by a factor of 10 faster than the analogous silanes with branched alkyl residues 5 Classification editDepending on the substitution pattern of the silicon atom a further distinction can be made Organosilanols are classified as organosilanetriols when three hydroxy groups and an organic residue are bound to a silicon atom e g methylsilanetriol phenylsilanetriol organosilandiols when two hydroxy groups and two organic residues are bound to a silicon atom e g dimethylsilanediol diphenylsilanediol organosilanols when one hydroxy group and three organic residues are bound to a silicon atom e g trimethylsilanol triethylsilanol or triphenylsilanol References edit IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 silanols doi 10 1351 goldbook S05664 Paul D Lickiss 1995 The synthesis and structure of organosilanols Advances in Inorganic Chemistry vol 42 pp 147 262 doi 10 1016 S0898 8838 08 60053 7 Rudolf Pietschnig Stefan Spirk 2016 The Chemistry of Organo Silanetriols Coordination Chemistry Reviews vol 323 pp 87 106 doi 10 1016 j ccr 2016 03 010 a b Barry Arkles Silanes pdf Gelest p 50 Retrieved 2016 12 10 G Schott C Harzdorf October 1960 Silane I Alkalische Solvolyse von Triorganosilanen Zeitschrift fur anorganische und allgemeine Chemie in German vol 306 no 3 4 pp 180 190 doi 10 1002 zaac 19603060306 nbsp Wikimedia Commons has media related to Organosilanole Retrieved from https en wikipedia org w index php title Organosilanols amp oldid 1161427348, wikipedia, wiki, book, books, library,
