Triphenylphosphine selenide

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Triphenylphosphine selenide
Ph3PSe.svg
Names
Preferred IUPAC name
Triphenyl-λ5-phosphaneselone
Other names
triphenylphosphane selenide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.279 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 223-406-1
PubChem CID
UNII
  • InChI=1S/C18H15PSe/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
    Key: ZFVJLNKVUKIPPI-UHFFFAOYSA-N
  • c1ccc(cc1)P(=[Se])(c2ccccc2)c3ccccc3
Properties
C18H15PSe
Molar mass 341.25
Appearancewhite solid
Melting point 186.5 to 187.5
insoluble
Solubility very soluble in dichloromethane, pyridine, and THF; moderately soluble on heating in acetonitrile, ethanol, and methanol; insoluble in ether [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triphenylphosphine selenide is an organophosphorus compound with the formula (C6H5)3PSe. It is a white solid which is soluble in most organic solvents. The compound is used in the preparation of other selenium compounds and is itself prepared by the reaction of triphenylphosphine with potassium selenocyanate. [2] Single crystals have been isolated with both monoclinic [3] and triclinic [4] structures (space groups: P21/c and P1 respectively); in both cases the geometry at phosphorus is tetrahedral.

See also

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Wilkinsons catalyst Chemical compound

Wilkinson's catalyst is the common name for chloridotris(triphenylphosphine)rhodium(I), a coordination complex of rhodium with the formula [RhCl(PPh3)3] (Ph = phenyl). It is a red-brown colored solid that is soluble in hydrocarbon solvents such as benzene, and more so in tetrahydrofuran or chlorinated solvents such as dichloromethane. The compound is widely used as a catalyst for hydrogenation of alkenes. It is named after chemist and Nobel laureate Sir Geoffrey Wilkinson, who first popularized its use.

The phosphonium cation describes polyatomic cations with the chemical formula PR+
4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

Triphenylphosphine 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 widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Palladium(II) chloride Chemical compound

Palladium(II) chloride, also known as palladium dichloride and palladous chloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value in organic synthesis. It is prepared by the reaction of chlorine with palladium metal at high temperatures.

Zeises salt Chemical compound

Zeise's salt, potassium trichloro(ethylene)platinate(II), is the chemical compound with the formula K[PtCl3(C2H4)]·H2O. The anion of this air-stable, yellow, coordination complex contains an η2-ethylene ligand. The anion features a platinum atom with a square planar geometry. The salt is of historical importance in the area of organometallic chemistry as one of the first examples of a transition metal alkene complex and is named for its discoverer, William Christopher Zeise.

Chloro(triphenylphosphine)gold(I) Chemical compound

Chloro(triphenylphosphine)gold(I) or triphenylphosphinegold(I) chloride is a coordination complex with the formula (Ph3P)AuCl. This colorless solid is a common reagent for research on gold compounds.

Triphenylphosphine oxide Chemical compound

Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C6H5)3, also written as Ph3PO or PPh3O (Ph = C6H5). This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine. It is a popular reagent to induce the crystallizing of chemical compounds.

Tetraphenylphosphonium chloride Chemical compound

Tetraphenylphosphonium chloride is the chemical compound with the formula (C6H5)4PCl, abbreviated Ph4PCl or PPh4Cl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in gravimetric analysis of perchlorate and related oxyanions. This colourless salt is used to generate lipophilic salts from inorganic and organometallic anions. Thus, Ph4P+ is useful as a phase-transfer catalyst, again because it allows inorganic anions to dissolve in organic solvents.

Bis(triphenylphosphine)palladium chloride Chemical compound

Bis(triphenylphosphine)palladium chloride is a coordination compound of palladium containing two triphenylphosphine and two chloride ligands. It is a yellow solid that is soluble in some organic solvents. It is used for palladium-catalyzed coupling reactions, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Many analogous complexes are known with different phosphine ligands.

Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity.

Organoplatinum chemistry is the chemistry of organometallic compounds containing a carbon to platinum chemical bond, and the study of platinum as a catalyst in organic reactions. Organoplatinum compounds exist in oxidation state 0 to IV, with oxidation state II most abundant. The general order in bond strength is Pt-C (sp) > Pt-O > Pt-N > Pt-C (sp3). Organoplatinum and organopalladium chemistry are similar, but organoplatinum compounds are more stable and therefore less useful as catalysts.

Uranium pentachloride Chemical compound

Uranium pentachloride is an inorganic chemical compound composed of uranium in the +5 oxidation state and five chlorine atoms.

Uranium pentabromide Chemical compound

Uranium pentabromide is an inorganic chemical compound with the formula UBr5.

Potassium selenocyanate Chemical compound

Potassium selenocyanate is the inorganic compound with the formula KSeCN. It is a hygroscopic white solid that is soluble in water, decomposing in air to red selenium and potassium cyanide. The compound has been characterized by X-ray crystallography, which confirms that it is a salt. The C-N and C-Se distances are 112 and 183 pm, respectively consistent with triple and single bonds.

Hydridotetrakis(triphenylphosphine)rhodium(I) Chemical compound

Hydridotetrakis(triphenylphosphine)rhodium(I) is the coordination complex with the formula HRh[P(C6H5)3]4. It consists of a Rh(I) center complexed to four triphenylphosphine (PPh3) ligands and one hydride. The molecule has idealized C3v symmetry. The compound is a homogeneous catalyst for hydrogenation and related reactions. It is a yellow solid that dissolves in aromatic solvents.

The selenide iodides are chemical compounds that contain both selenide ions (Se2−) and iodide ions (I) and one or metal atoms. They are in the class of mixed anion compounds or chalcogenide halides.

Pentaphenylphosphorus Chemical compound

Pentaphenylphosphorus is an organic phosphorane containing five phenyl groups connected to a central phosphorus atom. The phosphorus atom is considered to be in the +5 oxidation state. The chemical formula could be written as P(C6H5)5 or Ph5P, where Ph represents the phenyl group. It was discovered and reported in 1949 by Georg Wittig.

References

  1. Mayhew, D. L., Clive, D. L. J., Stawinski, J. and Bollmark, M. 2004. Triphenylphosphine Selenide. e-EROS Encyclopedia of Reagents for Organic Synthesis doi:10.1002/047084289X.rt378.pub2
  2. Philip Nicpon, Devon W. Meek "Triphenylphosphine Selenide" Inorganic Syntheses, 1967, Volume 10, 157–159. doi : 10.1002/9780470132418.ch23
  3. Codding, P. W.; Kerr, K. A. (15 May 1979). "Triphenylphosphine selenide". Acta Crystallographica Section B. 35 (5): 1261–1263. doi: 10.1107/S0567740879006129 .
  4. Jones, P. G.; Kienitz, C.; Thöne, C. (January 1994). "Crystal structure of triphenylphosphine selenide (triclinic), C18H15PSe". Zeitschrift für Kristallographie. 209 (1): 80–81. Bibcode:1994ZK....209...80J. doi:10.1524/zkri.1994.209.1.80.