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Revision as of 16:39, 21 December 2024 editSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,539 edits →Synthesis and reactions: stiborane connection← Previous edit Latest revision as of 16:42, 21 December 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,539 edits →Synthesis and reactions: more encyclopedic style 
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==Synthesis and reactions== ==Synthesis and reactions==
SbPh<sub>3</sub> 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> 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>

: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 :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


An alternative method treats ] 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> 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>


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> 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>

Latest revision as of 16:42, 21 December 2024

Triphenylstibine
Ball-and-stick model of the triphenylstibine molecule
Names
Preferred IUPAC name Triphenylstibane
Other names Triphenylantimony
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.125 Edit this at Wikidata
EC Number
  • 210-037-6
PubChem CID
RTECS number
  • WJ1400000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N
  • 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/h1-15HKey: HVYVMSPIJIWUNA-KWOBPOEBAA
SMILES
  • c3c((c1ccccc1)c2ccccc2)cccc3
Properties
Chemical formula C18H15Sb
Molar mass 353.07 g/mol
Appearance Colourless solid
Density 1.53 g/cm
Melting point 52 to 54 °C (126 to 129 °F; 325 to 327 K)
Boiling point 377 °C (711 °F; 650 K)
Solubility in water insoluble
Structure
Molecular shape trigonal pyramidal
Related compounds
Related compounds Triphenylamine
Triphenylphosphine
Triphenylarsine
Stibine
Hazards
Occupational safety and health (OHS/OSH):
Main hazards mildly toxic
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H302, H332, H411
Precautionary statements P261, P264, P270, P271, P273, P301+P310, P301+P312, P304+P312, P304+P340, P312, P330, P391, P405
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Triphenylstibine is the chemical compound with the formula Sb(C6H5)3, which is often abbreviated SbPh3, This colourless solid is a common organoantimony(III) compound. It serves as a ligand in coordination chemistry and as a reagent in organic synthesis.

Like the related molecules triphenylamine, triphenylphosphine and triphenylarsine, SbPh3 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°.

Synthesis and reactions

Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene:

6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl

In an alternative method, phenylmagnesium bromide is treated with SbCl3.

Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:

Sb(C6H5)3 + 2SbCl3 → 3Sb(C6H5)Cl2

Stiboranes can be synthesised from triphenylstibine by halogenation:

Sb(C6H5)3 + Cl2 → Sb(C6H5)3Cl2

As confirmed by X-ray crystallography, Sb(C6H5)3Cl2 features pentacoordinate Sb(V) with trans-diaxial chloride ligands.

References

  1. "Triphenylantimony". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  2. C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
  3. Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of Triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. doi:10.1107/S0108270189012862
  4. Michaelis, August; Reese, A. (1886). "Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen". Liebigs Annalen der Chemie. 233: 39-60. doi:10.1002/jlac.18862330104.
  5. Hiers, G. S. (1927). "Triphenylstibine". Organic Syntheses. 7: 80. doi:10.15227/orgsyn.007.0080.
  6. Ateş, Mustafa; Breunig, Hans Joachim; Güleç, Sabahittin; Offermann, Werner; Häberle, Karl; Dräger, Martin (1989). "Synthesen und Strukturen von Ethyl-, Propyl-, Butyl- und Mesitylantimon". Chemische Berichte. 122 (3): 473–478. doi:10.1002/cber.19891220313.
  7. Begley, M. J.; Sowerby, D. B. (1993). "Structures of triphenylantimony(V) dibromide and dichloride". Acta Crystallographica Section C Crystal Structure Communications. 49 (6): 1044–1046. Bibcode:1993AcCrC..49.1044B. doi:10.1107/S0108270192011958.
Antimony compounds
Antimonides
Sb(III)
Organoantimony(III) compounds
Sb(III,V)
Sb(V)
Organoantimony(V) compounds
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