| Revision as of 14:24, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 402703266 of page Triphenylstibine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:42, 21 December 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,404 edits →Synthesis and reactions: more encyclopedic style |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 402701600 |
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|verifiedrevid = 470616981 |
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| Name = Triphenylstibine |
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|Name = Triphenylstibine |
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| ImageFile = Triphenylphosphine-3D-sticks.png |
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|ImageFile1 = Triphenylstibine-3D-balls.png |
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<!-- | ImageSize = 100px --> |
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|ImageAlt1 = Ball-and-stick model of the triphenylstibine molecule |
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| ImageName = 3D structure of PPh<sub>3</sub> |
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|ImageFile2 = Triphenylstibine_crystals.jpg |
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| IUPACName = Triphenylstibine |
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| OtherNames = Triphenylantimony |
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|PIN = Triphenylstibane |
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|OtherNames = Triphenylantimony |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 603-36-1 |
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| ChemSpiderID = 11284 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 11777 |
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|ChemSpiderID = 11284 |
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| InChI = 1/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;/rC18H15Sb/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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|EC_number = 210-037-6 |
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| InChIKey = HVYVMSPIJIWUNA-KWOBPOEBAA |
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|PubChem = 11777 |
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| SMILES = c3c((c1ccccc1)c2ccccc2)cccc3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = G1X1263AMM |
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| StdInChI = 1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H; |
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|RTECS = WJ1400000 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|InChI = 1/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;/rC18H15Sb/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
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| StdInChIKey = HVYVMSPIJIWUNA-UHFFFAOYSA-N |
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|InChIKey = HVYVMSPIJIWUNA-KWOBPOEBAA |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|SMILES = c3c((c1ccccc1)c2ccccc2)cccc3 |
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| CASNo = 603-36-1 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = WJ1400000 |
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|StdInChI = 1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H; |
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}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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|StdInChIKey = HVYVMSPIJIWUNA-UHFFFAOYSA-N |
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| Formula = C<sub>18</sub>H<sub>15</sub>Sb |
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| MolarMass = 353.07 g/mol |
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| Appearance = Colourless solid |
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| Density = 1.53 g/cm<sup>3</sup> |
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| Solubility = insoluble |
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| MeltingPt = 52-54 °C |
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| BoilingPt = 377 °C |
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}} |
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| Section3 = {{Chembox Structure |
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| MolShape = ] |
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| Dipole = |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| MainHazards = mildly toxic |
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| NFPA-H = 1 |
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| NFPA-F = |
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| NFPA-R = |
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| RPhrases = 20/22-51/53 |
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| SPhrases = 61 |
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}} |
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| Section8 = {{Chembox Related |
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| OtherCpds = ]<br />]<br />]}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = C<sub>18</sub>H<sub>15</sub>Sb |
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|MolarMass = 353.07 g/mol |
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|Appearance = Colourless solid |
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|Density = 1.53 g/cm<sup>3</sup> |
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|Solubility = insoluble |
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|MeltingPtC = 52 to 54 |
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|BoilingPtC = 377 |
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}} |
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|Section3={{Chembox Structure |
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|MolShape = ] |
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}} |
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|Section7={{Chembox Hazards |
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|MainHazards = mildly toxic |
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|NFPA-H = 1 |
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|GHS_ref=<ref>{{cite web |title=Triphenylantimony |url=https://pubchem.ncbi.nlm.nih.gov/compound/11777#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}</ref> |
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|GHSPictograms = {{GHS06}}{{GHS07}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|301|302|332|411}} |
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|PPhrases = {{P-phrases|261|264|270|271|273|301+310|301+312|304+312|304+340|312|330|391|405}} |
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}} |
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|Section4={{Chembox Related |
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|OtherCompounds = ]<br>]<br />]<br />]}} |
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}} |
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'''Triphenylstibine''' is the ] with the ] Sb(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>, which is often abbreviated SbPh<sub>3</sub>, This colourless solid is a common ](III) compound. It serves as a ] in ]<ref name=McAuliffe>{{cite book|editor=C. A. McAuliffe|title=Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands|publisher=J. Wiley|year=1973|isbn=0-470-58117-4}}</ref> and as a reagent in ]. |
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Like the related molecules ], ] and ], SbPh<sub>3</sub> is pyramidal with a propeller-like arrangement of the phenyl groups. The Sb-C distances average 2.14-2.17 Å and the C-Sb-C angles are 95°.<ref>Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of Triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. {{doi|10.1107/S0108270189012862}}</ref> |
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==Synthesis and reactions== |
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Triphenylstibine was first reported in 1886, being prepared from ] and ]:<ref>{{cite journal|first1=August|last1=Michaelis|last2=Reese|first2= A.|title=Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen|journal=Liebigs Annalen der Chemie|volume=233|page=39-60|year=1886|doi=10.1002/jlac.18862330104}}<!--yes, Ueber, no umlaut--></ref> |
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:6 Na + 3 C<sub>6</sub>H<sub>5</sub>Cl + SbCl<sub>3</sub> → (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Sb + 6 NaCl |
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In an alternative method, ] is treated with SbCl<sub>3</sub>.<ref>{{cite journal|author=Hiers, G. S.|title=Triphenylstibine|journal=Organic Syntheses|year=1927|volume=7|page=80|doi=10.15227/orgsyn.007.0080}}</ref> |
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Upon treatment with ], triphenylstibine undergoes a ]:<ref>{{cite journal |doi=10.1002/cber.19891220313 |title=Synthesen und Strukturen von Ethyl-, Propyl-, Butyl- und Mesitylantimon |date=1989 |last1=Ateş |first1=Mustafa |last2=Breunig |first2=Hans Joachim |last3=Güleç |first3=Sabahittin |last4=Offermann |first4=Werner |last5=Häberle |first5=Karl |last6=Dräger |first6=Martin |journal=Chemische Berichte |volume=122 |issue=3 |pages=473–478 }}</ref> |
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:{{chem2| Sb(C6H5)3 + 2SbCl3 -> 3Sb(C6H5)Cl2}} |
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]s can be synthesised from triphenylstibine by halogenation: |
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:{{chem2|Sb(C6H5)3 + Cl2 -> Sb(C6H5)3Cl2}} |
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As confirmed by ], {{chem2|Sb(C6H5)3Cl2}} features pentacoordinate Sb(V) with trans-diaxial chloride ligands.<ref>{{cite journal |doi=10.1107/S0108270192011958 |title=Structures of triphenylantimony(V) dibromide and dichloride |date=1993 |last1=Begley |first1=M. J. |last2=Sowerby |first2=D. B. |journal=Acta Crystallographica Section C Crystal Structure Communications |volume=49 |issue=6 |pages=1044–1046 |bibcode=1993AcCrC..49.1044B }}</ref> |
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==References== |
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{{reflist}}{{Antimony compounds}} |
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] |
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] |