Dichloro(1,2-bis(diphenylphosphino)ethane)nickel

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Dichloro[1,2-bis(diphenyl­phosphino)ethane]nickel
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NiCl2(dppe).jpg
Identifiers
3D model (JSmol)
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PubChem CID
  • InChI=1S/C26H24P2.2ClH.Ni/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26;;;/h1-20H,21-22H2;2*1H;/q;;;+2/p-2
    Key: XXECWTBMGGXMKP-UHFFFAOYSA-L
  • Cl[Ni]1(Cl)[P](c2ccccc2)(c2ccccc2)CC[P]1(c1ccccc1)c1ccccc1
Properties
C26H24Cl2NiP2
Molar mass 528.02 g·mol−1
Appearanceorange solid
Density 1.406 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichloro[1,2-bis(diphenylphosphino)ethane]nickel is a coordination complex with the formula NiCl2(dppe); where dppe is the diphosphine 1,2-bis(diphenylphosphino)ethane. It is used as a reagent and as a catalyst. [1] The compound is a bright orange-red diamagnetic solid. The complex adopts a square planar geometry. [2] [3]

It is prepared by combining equimolar portions of nickel(II) chloride hexahydrate with dppe:

Ni(H2O)6Cl2 + dppe → NiCl2(dppe) + 6 H2O

See also

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Nickel(II) chloride (or just nickel chloride) is the chemical compound NiCl2. The anhydrous salt is yellow, but the more familiar hydrate NiCl2·6H2O is green. Nickel(II) chloride, in various forms, is the most important source of nickel for chemical synthesis. The nickel chlorides are deliquescent, absorbing moisture from the air to form a solution. Nickel salts have been shown to be carcinogenic to the lungs and nasal passages in cases of long-term inhalation exposure.

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

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1,5-Cyclooctadiene is a cyclic hydrocarbon with the chemical formula C8H12, specifically [−(CH2)2−CH=CH−]2.

<span class="mw-page-title-main">1,2-Bis(diphenylphosphino)ethane</span> Chemical compound

1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.

<span class="mw-page-title-main">Nickel(II) iodide</span> Chemical compound

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<span class="mw-page-title-main">1,1'-Bis(diphenylphosphino)ferrocene</span> Chemical compound

1,1-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe).

<span class="mw-page-title-main">Diphosphine ligands</span>

Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry. They are identified by the presence of two phosphino groups linked by a backbone, and are usually chelating. A wide variety of diphosphines have been synthesized with different linkers and R-groups. Alteration of the linker and R-groups alters the electronic and steric properties of the ligands which can result in different coordination geometries and catalytic behavior in homogeneous catalysts.

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

Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C6H5)2PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts.

<span class="mw-page-title-main">1,3-Bis(diphenylphosphino)propane</span> Chemical compound

1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.

<span class="mw-page-title-main">1,2-Bis(dimethylphosphino)ethane</span> Chemical compound

1,2-Bis(dimethylphosphino)ethane (dmpe) is a diphosphine ligand in coordination chemistry. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CH2PMe2)2, dmpe is used as a compact strongly basic spectator ligand (Me = methyl), Representative complexes include V(dmpe)2(BH4)2, Mn(dmpe)2(AlH4)2, Tc(dmpe)2(CO)2Cl, and Ni(dmpe)Cl2.

<span class="mw-page-title-main">Dichlorotris(triphenylphosphine)ruthenium(II)</span> Chemical compound

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<span class="mw-page-title-main">Dichloro(1,3-bis(diphenylphosphino)propane)nickel</span> Chemical compound

Dichloro[1,3-bis(diphenylphosphino)propane]nickel a coordination complex with the formula NiCl2(dppp); where dppp is the diphosphine 1,3-bis(diphenylphosphino)propane. It is used as a catalyst in organic synthesis. The compound is a bright orange-red crystalline powder.

Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH
3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

<span class="mw-page-title-main">Metal-phosphine complex</span>

A metal-phosphine complex is a coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. Prominent examples of metal phosphine complexes include Wilkinson's catalyst (Rh(PPh3)3Cl), Grubbs' catalyst, and tetrakis(triphenylphosphine)palladium(0).

Nickel(II) nitrite is an inorganic compound with the chemical formula Ni(NO2)2. Anhydrous nickel nitrite was first discovered in 1961 by Cyril Clifford Addison, who allowed gaseous nickel tetracarbonyl to react with dinitrogen tetroxide, yielding a green smoke. Nickel nitrite was the second transition element anhydrous nitrite discovered after silver nitrite.

<span class="mw-page-title-main">Bis(dinitrogen)bis(1,2-bis(diphenylphosphino)ethane)molybdenum(0)</span> Chemical compound

trans-Bis(dinitrogen)bis[1,2-bis(diphenylphosphino)ethane]molybdenum(0) is a coordination complex with the formula Mo(N2)2(dppe)2. It is a relatively air stable yellow-orange solid. It is notable as being the first discovered dinitrogen containing complex of molybdenum.

<span class="mw-page-title-main">Dichlorobis(triphenylphosphine)nickel(II)</span> Chemical compound

Dichlorobis(triphenylphosphine)nickel(II) refers to a pair of metal phosphine complexes with the formula NiCl2[P(C6H5)3]2. The compound exists as two isomers, a paramagnetic dark blue solid and a diamagnetic red solid. These complexes function as catalysts for organic synthesis.

Nickel compounds are chemical compounds containing the element nickel which is a member of the group 10 of the periodic table. Most compounds in the group have an oxidation state of +2. Nickel is classified as a transition metal with nickel(II) having much chemical behaviour in common with iron(II) and cobalt(II). Many salts of nickel(II) are isomorphous with salts of magnesium due to the ionic radii of the cations being almost the same. Nickel forms many coordination complexes. Nickel tetracarbonyl was the first pure metal carbonyl produced, and is unusual in its volatility. Metalloproteins containing nickel are found in biological systems.

<span class="mw-page-title-main">1,4-Bis(diphenylphosphino)butane</span> Chemical compound

1,4-Bis(diphenylphosphino)butane (dppb) is an organophosphorus compound with the formula (Ph2PCH2CH2)2. It is less commonly used in coordination chemistry than other diphosphine ligands such as dppe. It is a white solid that is soluble in organic solvents.

<span class="mw-page-title-main">Transition metal complexes of phosphine oxides</span>

Transition metal complexes of phosphine oxides are coordination complex containing one or more phosphine oxide ligands. Many phosphine oxides exist and most behave as hard Lewis bases. Almost invariably, phosphine oxides bind metals by formation of M-O bonds.

References

  1. Kumada, Makota; Tamao, Kohei; Sumitani, Koji (1978). "Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-Dibutylbenzene". Organic Syntheses. 58: 127. doi:10.15227/orgsyn.058.0127.
  2. Van Hecke, Gerald R.; Horrocks, Jr., William DeW. (1966). "Ditertiary Phosphine Complexes of Nickel. Spectral, Magnetic, and Proton Resonance Studies. A Planar-Tetrahedral Equilibrium". Inorganic Chemistry. 5 (11): 1968–1974. doi:10.1021/ic50045a029.
  3. Davison, J. C.; Foreman, M. R. St.-J.; Howie, R. A.; Plater, M.J.; Skakle, J. M. S. (2001). "A New Polymorph, Form C, of [1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)". Acta Crystallogr. C. 57 (6): 690–693. doi:10.1107/S0108270101003961. PMID   11408672.