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A transition metal alkenyl complex is an
According to the 
organometallic compound
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and ...
containing a metal
A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, electricity and thermal conductivity, heat relatively well. These properties are all associated wit ...
bound to a alkenyl group
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as α-olefins.
The International Union of Pu ...
(i.e., the motif M-CR=CRR'). The simplest alkenyl ligand is vinyl.
Ligand properties
According to the covalent bond classification method The covalent bond classification (CBC) method, also referred to as LXZ notation, is a way of describing covalent compounds such as organometallic complexes in a way that is not prone to limitations resulting from the definition of oxidation state. ...
, a terminal alkenyl
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as α-olefins.
The International Union of Pu ...
is an anionic X-type ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
.
Some alkenyl ligands are bridging ligand
In coordination chemistry, a bridging ligand is a ligand that connects two or more atoms, usually metal ions. The ligand may be atomic or polyatomic. Virtually all complex organic compounds can serve as bridging ligands, so the term is usually r ...
s, in which case they provide 3 electrons to the pair of metals. A third class of alkenyl ligands bind in an η2- mode. They are also 3-electron ligands.
Synthesis and occurrence
In the laboratory preparations, alkenyl complexes are often prepared by salt metathesis usingvinyl lithium
Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations..
Pr ...
or vinyl Grignard reagent
Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...
s. They also arise by protonation of alkyne complex
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Acetylene
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Propyne
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1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no ...
es. Oxidative addition
Oxidative addition and reductive elimination are two important and related classes of reactions in organometallic chemistry. Oxidative addition is a process that increases both the oxidation state and coordination number of a metal centre. Oxidat ...
of vinyl halides gives alkenyl complexes:
: (Ph = phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...
)
Homoleptic vinyl complexes are unknown, but a trivinyl complex has been characterized.
Metal alkenyl complexes are intermediates in the semihydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
of alkynes to alkenes
References