Triphenylstibine

Last updated
Triphenylstibine
Triphenylstibine-3D-balls.png
Triphenylstibine crystals.jpg
Names
Preferred IUPAC name
Triphenylstibane
Other names
Triphenylantimony
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.125 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-037-6
PubChem CID
RTECS number
  • WJ1400000
UNII
  • InChI=1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H; Yes check.svgY
    Key: HVYVMSPIJIWUNA-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColourless 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]
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

SbPh3 was first reported in 1886, being prepared from antimony trichloride and chlorobenzene: [4]

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

An alternative method treats phenylmagnesium bromide with SbCl3. [5]

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

Sb(C6H5)3 + 2SbCl3 → 3Sb(C6H5)Cl2

Related Research Articles

<span class="mw-page-title-main">Antimony</span> Chemical element with atomic number 51 (Sb)

Antimony is a chemical element; it has symbol Sb (from Latin stibium) and atomic number 51. A lustrous grey metal or metalloid, it is found in nature mainly as the sulfide mineral stibnite (Sb2S3). Antimony compounds have been known since ancient times and were powdered for use as medicine and cosmetics, often known by the Arabic name kohl. The earliest known description of this metalloid in the West was written in 1540 by Vannoccio Biringuccio.

<span class="mw-page-title-main">Arsine</span> Chemical compound

Arsine (IUPAC name: arsane) is an inorganic compound with the formula AsH3. This flammable, pyrophoric, and highly toxic pnictogen hydride gas is one of the simplest compounds of arsenic. Despite its lethality, it finds some applications in the semiconductor industry and for the synthesis of organoarsenic compounds. The term arsine is commonly used to describe a class of organoarsenic compounds of the formula AsH3−xRx, where R = aryl or alkyl. For example, As(C6H5)3, called triphenylarsine, is referred to as "an arsine".

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.

<span class="mw-page-title-main">Aluminium chloride</span> Chemical compound

Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Stibine</span> Chemical compound

Stibine (IUPAC name: stibane) is a chemical compound with the formula SbH3. A pnictogen hydride, this colourless, highly toxic gas is the principal covalent hydride of antimony, and a heavy analogue of ammonia. The molecule is pyramidal with H–Sb–H angles of 91.7° and Sb–H distances of 170.7 pm (1.707 Å). The smell of this compound from usual sources (like from reduction of antimony compounds) is reminiscent of arsine, i.e. garlic-like.

<span class="mw-page-title-main">Rhodium(III) chloride</span> Chemical compound

Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic red-brown solids. The soluble trihydrated (n = 3) salt is the usual compound of commerce. It is widely used to prepare compounds used in homogeneous catalysis.

<span class="mw-page-title-main">Antimony oxychloride</span> Chemical compound

Antimony oxychloride, known since the 15th century, has been known by a plethora of alchemical names. Since the compound functions as both an emetic and a laxative, it was originally used as a purgative.

<span class="mw-page-title-main">Arsenic trichloride</span> Chemical compound

Arsenic trichloride is an inorganic compound with the formula AsCl3, also known as arsenous chloride or butter of arsenic. This poisonous oil is colourless, although impure samples may appear yellow. It is an intermediate in the manufacture of organoarsenic compounds.

<span class="mw-page-title-main">Antimony trichloride</span> Chemical compound

Antimony trichloride is the chemical compound with the formula SbCl3. It is a soft colorless solid with a pungent odor and was known to alchemists as butter of antimony.

<span class="mw-page-title-main">Bis(benzene)chromium</span> Chemical compound

Bis(benzene)chromium is the organometallic compound with the formula Cr(η6-C6H6)2. It is sometimes called dibenzenechromium. The compound played an important role in the development of sandwich compounds in organometallic chemistry and is the prototypical complex containing two arene ligands.

<span class="mw-page-title-main">Triphenylarsine</span> Chemical compound

Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.

<span class="mw-page-title-main">Organoaluminium chemistry</span>

Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species. Industrially, these compounds are mainly used for the production of polyolefins.

Organophosphines are organophosphorus compounds with the formula PRnH3−n, where R is an organic substituent. These compounds can be classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures. Organophosphines are generally colorless, lipophilic liquids or solids. The parent of the organophosphines is phosphine (PH3).

<span class="mw-page-title-main">Chlorodiphenylphosphine</span> Chemical compound

Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is useful reagent for introducing the Ph2P group into molecules, which includes many ligands. Like other halophosphines, Ph2PCl is reactive with many nucleophiles such as water and easily oxidized even by air.

Organoantimony chemistry is the chemistry of compounds containing a carbon to antimony (Sb) chemical bond. Relevant oxidation states are SbV and SbIII. The toxicity of antimony limits practical application in organic chemistry.

<span class="mw-page-title-main">2-Phenylpyridine</span> Chemical compound

2-Phenylpyridine is an organic compound with the formula C6H5C5H4N (or C11H9N). It is a colourless viscous liquid. The compound and related derivatives have attracted interest as precursors to highly fluorescent metal complexes of possible value as organic light emitting diodes (OLEDs).

Cobalt(III) chloride or cobaltic chloride is an unstable and elusive compound of cobalt and chlorine with formula CoCl
3
. In this compound, the cobalt atoms have a formal charge of +3.

Among pnictogen group Lewis acidic compounds, unusual lewis acidity of Lewis acidic antimony compounds have long been exploited as both stable conjugate acids of non-coordinating anions, and strong Lewis acid counterparts of well-known superacids. Also, Lewis-acidic antimony compounds have recently been investigated to extend the chemistry of boron because of the isolobal analogy between the vacant p orbital of borane and σ*(Sb–X) orbitals of stiborane, and the similar electronegativities of antimony (2.05) and boron (2.04).

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.