Organometallic chemistry

organometallicorganometallic compoundorganometallic compoundsorganometallic chemistorganometallic complexorganometallicsorganometallic reagentHistory of organometallic chemistryorganometallic complexesorganometalllic 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 alkaline, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and tin, as well.wikipedia
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Inorganic chemistry

inorganicinorganic chemistinorganic compounds
The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
Inorganic chemistry deals with the synthesis and behavior of inorganic and organometallic compounds.

Ferrocene

FcFerrocene, (C 5 H 5 ) 2 Feferrocenyl
Tetracarbonyl nickel, and ferrocene are examples of organometallic compounds containing transition metals.
Ferrocene is an organometallic compound with the formula Fe(C5H5)2.

Homogeneous catalysis

homogeneous catalysthomogeneoushomogeneous catalysts
Organometallic compounds are widely used both stoichiometrically in research and industrial chemical reactions, as well as in the role of catalysts to increase the rates of such reactions (e.g., as in uses of homogeneous catalysis), where target molecules include polymers, pharmaceuticals, and many other types of practical products.
The term is used almost exclusively to describe solutions and often implies catalysis by organometallic compounds.

Organic chemistry

organicorganic chemistorganic chemical
The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
Organometallic chemistry is the study of compounds containing carbon–metal bonds.

Bioorganometallic chemistry

Bioorganometallic
This subset of complexes is often discussed within the subfield of bioorganometallic chemistry.
Due to the recent (21st century) discovery of new systems containing carbon-metal bonds in biology, bioorganometallic chemistry is rapidly emerging as a distinct subdiscipline of bioinorganic chemistry that straddles organometallic chemistry and biochemistry.

18-electron rule

18-electron18 electron rule18-electron complex
The 18-electron rule is helpful in predicting the stabilities of metal carbonyls and related compounds.
The 18-electron rule is a rule used primarily for predicting and rationalizing formulas for stable metal complexes, especially organometallic compounds.

Isolobal principle

isolobalisolobal analogy
Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the isolobal principle.
The isolobal principle (more formally known as the isolobal analogy) is a strategy used in organometallic chemistry to relate the structure of organic and inorganic molecular fragments in order to predict bonding properties of organometallic compounds.

Copper

CuCu 2+ cupric
Examples of such organometallic compounds include all Gilman reagents, which contain lithium and copper.
Copper compounds, whether organic complexes or organometallics, promote or catalyse numerous chemical and biological processes.

Transmetalation

transmetallationtransmetalatetransmetalating
spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another.

Oxidative addition

C-H oxidative additionOxidative addition and reductive eliminationoxidative insertion
Using transition-metals that are in their highest oxidation state prevents other reactions from occurring, such as oxidative addition.
Oxidative addition and reductive elimination are two important and related classes of reactions in organometallic chemistry.

Reductive elimination

oxidative addition and reductive eliminationreductively eliminate
Reductive elimination is an elementary step in organometallic chemistry in which the oxidation state of the metal center decreases while forming a new covalent bond between two ligands.

Ligand

ligandsligand exchangebidentate ligand
Many complexes feature coordination bonds between a metal and organic ligands.
Especially in the area of organometallic chemistry, ligands are classified as L and X (or combinations of the two).

Carbon–hydrogen bond activation

C-H activationC-H bond activationC–H activation
Reactions classified by the term typically involve the hydrocarbon first to react with a metal catalyst to create an organometallic complex in which the hydrocarbon is coordinated to the inner-sphere of a metal, either via an intermediate "alkane or arene complex" or as a transition state leading to a "M−C" intermediate.

Migratory insertion

1,1- migratory insertioninsertionmigration
A migratory insertion is a type of reaction in organometallic chemistry wherein two ligands on a metal complex combine.

Metallacycle

cyclometalationmetallacyclobutanemetallocycle
In organometallic chemistry, a metallacycle is a derivative of a carbocyclic compound wherein a metal has replaced at least one carbon center; this is to some extent similar to heterocycles.

Nucleophilic abstraction

Nucleophilic abstraction is a type of an organometallic reaction which can be defined as a nucleophilic attack on a ligand which causes part or all of the original ligand to be removed from the metal along with the nucleophile.

Coordinate covalent bond

dative bondcoordination bonddative covalent bond
Many complexes feature coordination bonds between a metal and organic ligands.
Metal-ligand interactions in most organometallic compounds and most coordination compounds are described similarly.

Associative substitution

associative mechanismassociativeassociative interchange
The terminology is typically applied to coordination and organometallic complexes, but resembles the Sn2 mechanism in organic chemistry.

William Christopher Zeise

Zeise
Early developments in organometallic chemistry include Louis Claude Cadet's synthesis of methyl arsenic compounds related to cacodyl, William Christopher Zeise's platinum-ethylene complex, Edward Frankland's discovery of diethyl- and dimethylzinc, Ludwig Mond's discovery of Ni(CO) 4, and Victor Grignard's organomagnesium compounds.
He is best known for synthesising one of the first organometallic compounds, named Zeise's salt in his honour.

Hydrometalation

Hydrometalation (hydrometallation) is a type of chemical reaction in organometallic chemistry in which a chemical compound with a hydrogen to metal bond (M-H, metal hydride) adds to compounds with an unsaturated bond like an alkene (RC=CR) forming a new compound with a carbon to metal bond (RHC-CRM).

Edward Frankland

Sir Edward FranklandE. FranklandFrankland
Early developments in organometallic chemistry include Louis Claude Cadet's synthesis of methyl arsenic compounds related to cacodyl, William Christopher Zeise's platinum-ethylene complex, Edward Frankland's discovery of diethyl- and dimethylzinc, Ludwig Mond's discovery of Ni(CO) 4, and Victor Grignard's organomagnesium compounds.
He was one of the originators of organometallic chemistry and introduced the concept of combining power or valence.

Coordination polymer

coordination polymerspolymeric
(Though not always acknowledged as an organometallic compound, Prussian blue, a mixed-valence iron-cyanide complex, was first prepared in 1706 by paint maker Johann Jacob Diesbach as the first coordination polymer and synthetic material containing a metal-carbon bond.
A coordination polymer is an inorganic or organometallic polymer structure containing metal cation centers linked by ligands.

Arsenic

AsAs 2 Arsenate
In addition to the traditional metals, lanthanides, actinides, and semimetals, elements such as boron, silicon, arsenic, and selenium are considered to form organometallic compounds, e.g. organoborane compounds such as triethylborane (Et 3 B).
Cadet's fuming liquid (impure cacodyl), often claimed as the first synthetic organometallic compound, was synthesized in 1760 by Louis Claude Cadet de Gassicourt by the reaction of potassium acetate with arsenic trioxide.

Electron counting

18 valence electronselectron count14 valence electron
As in other areas of chemistry, electron counting is useful for organizing organometallic chemistry.

Ernst Otto Fischer

FischerE. O. FischerE. Fischer
Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to Ernst Fischer and Geoffrey Wilkinson for work on metallocenes.
Ernst Otto Fischer (10 November 1918 – 23 July 2007) was a German chemist who won the Nobel Prize for pioneering work in the area of organometallic chemistry.