Triphenylstibine

Triphenylstibine
Ball-and-stick model of the triphenylstibine molecule
Names
Preferred IUPAC name
Triphenylstibane
Other names
Triphenylantimony
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.125 Edit this at Wikidata
EC Number
  • 210-037-6
RTECS number
  • WJ1400000
UNII
  • InChI=1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H; checkY
    Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N checkY
  • 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
    Key: HVYVMSPIJIWUNA-KWOBPOEBAA
  • c3c([Sb](c1ccccc1)c2ccccc2)cccc3
Properties
C18H15Sb
Molar mass 353.07 g/mol
Appearance Colourless solid
Density 1.53 g/cm3
Melting point 52 to 54 °C (126 to 129 °F; 325 to 327 K)
Boiling point 377 °C (711 °F; 650 K)
insoluble
Structure
trigonal pyramidal
Related compounds
Related compounds
 Triphenylamine
Triphenylphosphine
Triphenylarsine
Stibine
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 mildly toxic
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H302, H332, H411
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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[2] 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°.[3]

Synthesis and reactions

Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene:[4]

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

In an alternative method, phenylmagnesium bromide is treated with SbCl3.[5]

Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:[6]

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.[7]

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.