Triphenyl phosphite
Encyclopedia
Triphenyl phosphite is the chemical compound
with the formula
P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid
and phenol
. It is used as a ligand
in organometallic chemistry
. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation
of alkene
s.
Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a base:
Trimethylphosphine
is prepared from triphenylphosphite:
Triphenylphosphite is a notable example of polyamorphism
in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K.
:
It also forms a variety of Fe(O) and Fe(II) complexes such as the dihydride
H2Fe[P(OC6H5)3]4.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid
Phosphorous acid
Phosphorous acid is the compound described by the formula H3PO3. This acid is diprotic , not triprotic as might be suggested by this formula. Phosphorous acid is as an intermediate in the preparation of other phosphorus compounds.-Nomenclature and tautomerism:H3PO3 is more clearly described with...
and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
. It is used as a ligand
Ligand
In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...
in organometallic chemistry
Organometallic chemistry
Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character...
. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation
Hydrocyanation
Hydrocyanation is, most fundamentally, the process whereby H+ and –CN ions are added to a molecular substrate. Usually the substrate is an alkene and the product is a nitrile. When –CN is a ligand in a transition metal complex, its basicity makes it difficult to dislodge, so, in this...
of alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
s.
Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a base:
- PCl3 + 3 HOC6H5 → P(OC6H5)3 + 3 HCl
Trimethylphosphine
Trimethylphosphine
Trimethylphosphine is the organophosphorus compound with the formula P3, commonly abbreviated PMe3. This colorless liquid has a strongly unpleasant odour, which is characteristic of alkylphosphines. It is a pyramidal molecule with C3v symmetry, similar to ammonia and phosphine . As a ligand, its...
is prepared from triphenylphosphite:
- 3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5
Triphenylphosphite is a notable example of polyamorphism
Polyamorphism
Polyamorphism is the ability of a substance to exist in several different amorphous modifications. It is analogous to the polymorphism of crystalline materials. Many amorphous substances can exist with different amorphous characteristics . However, polyamorphism requires two distinct amorphous...
in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K.
Representative coordination complexes
Triphenylphosphite forms zero-valent complexes of the type M[P(OC6H5)3]4 for M = Ni, Pd, Pt. The colourless nickel complex (melting point 147 °C) can be prepared from the nickel(0) complex of 1,5-cyclooctadiene1,5-Cyclooctadiene
1,5-Cyclooctadiene is the organic compound with the chemical formula C8H12. Generally abbreviated COD, this diene is a useful precursor to other organic compounds and serves as a ligand in organometallic chemistry.- Synthesis :...
:
- Ni(COD)2 + 4 P(OC6H5)3 → Ni[P(OC6H5)3]4 + 2 COD
It also forms a variety of Fe(O) and Fe(II) complexes such as the dihydride
Hydride
In chemistry, a hydride is the anion of hydrogen, H−, or, more commonly, a compound in which one or more hydrogen centres have nucleophilic, reducing, or basic properties. In compounds that are regarded as hydrides, hydrogen is bonded to a more electropositive element or group...
H2Fe[P(OC6H5)3]4.