Organometallic chemistry
Overview
 
Organometallic chemistry is the study of chemical compound
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...

s containing bonds between carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 and a metal
Metal
A metal , is an element, compound, or alloy that is a good conductor of both electricity and heat. Metals are usually malleable and shiny, that is they reflect most of incident light...

. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character. Organometallic chemistry combines aspects of inorganic chemistry
Inorganic chemistry
Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry...

 and organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

.
Organometallic compounds are distinguished by the prefix "organo-" e.g. organopalladium compounds.
Encyclopedia
Organometallic chemistry is the study of chemical compound
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...

s containing bonds between carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 and a metal
Metal
A metal , is an element, compound, or alloy that is a good conductor of both electricity and heat. Metals are usually malleable and shiny, that is they reflect most of incident light...

. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character. Organometallic chemistry combines aspects of inorganic chemistry
Inorganic chemistry
Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry...

 and organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

.

Organometallic compounds

Organometallic compounds are distinguished by the prefix "organo-" e.g. organopalladium compounds. Examples of such organometallic compounds include all Gilman reagent
Gilman reagent
A Gilman reagent is a lithium and copper reagent compound, R2CuLi, where R is an organic radical. These are useful because they react with organic chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller...

s, which contain lithium
Lithium
Lithium is a soft, silver-white metal that belongs to the alkali metal group of chemical elements. It is represented by the symbol Li, and it has the atomic number 3. Under standard conditions it is the lightest metal and the least dense solid element. Like all alkali metals, lithium is highly...

 and copper
Copper
Copper is a chemical element with the symbol Cu and atomic number 29. It is a ductile metal with very high thermal and electrical conductivity. Pure copper is soft and malleable; an exposed surface has a reddish-orange tarnish...

. Tetracarbonyl nickel, and ferrocene
Ferrocene
Ferrocene is an organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds...

 are examples of organometallic compounds containing transition metal
Transition metal
The term transition metal has two possible meanings:*The IUPAC definition states that a transition metal is "an element whose atom has an incomplete d sub-shell, or which can give rise to cations with an incomplete d sub-shell." Group 12 elements are not transition metals in this definition.*Some...

s. Other examples include organomagnesium compounds like iodo(methyl)magnesium MeMgI, diethylmagnesium (Et2Mg), and all Grignard reagents; organolithium compounds such as n-butyllithium
N-Butyllithium
n-Butyllithium is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene...

 (n-BuLi), organozinc compounds such as diethylzinc
Diethylzinc
Diethylzinc 2Zn, or DEZn, is a highly pyrophoric organozinc compound consisting of a zinc center bound to two ethyl groups. This colourless liquid is an important reagent in organic chemistry and available commercially as a solution in hexanes, heptane, or toluene.-Synthesis:Edward Frankland first...

 (Et2Zn) and chloro(ethoxycarbonylmethyl)zinc (ClZnCH2C(=O)OEt); and organocopper compounds such as lithium dimethylcuprate (Li+[CuMe2]).

The term "metalorganics
Metalorganics
Metalorganic compounds are a class of chemical compounds that contain metals and organic ligands. Metalorganic compounds are used extensively in materials science in applications such as metalorganic vapour phase epitaxy or sol-gel processing using alkoxides...

" usually refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal beta-diketonates, alkoxides, and dialkylamides are representative members of this class.

In addition to the traditional metals, lanthanides, actinides, and semimetals, elements such as boron
Boron
Boron is the chemical element with atomic number 5 and the chemical symbol B. Boron is a metalloid. Because boron is not produced by stellar nucleosynthesis, it is a low-abundance element in both the solar system and the Earth's crust. However, boron is concentrated on Earth by the...

, silicon
Silicon
Silicon is a chemical element with the symbol Si and atomic number 14. A tetravalent metalloid, it is less reactive than its chemical analog carbon, the nonmetal directly above it in the periodic table, but more reactive than germanium, the metalloid directly below it in the table...

, arsenic
Arsenic
Arsenic is a chemical element with the symbol As, atomic number 33 and relative atomic mass 74.92. Arsenic occurs in many minerals, usually in conjunction with sulfur and metals, and also as a pure elemental crystal. It was first documented by Albertus Magnus in 1250.Arsenic is a metalloid...

, and selenium
Selenium
Selenium is a chemical element with atomic number 34, chemical symbol Se, and an atomic mass of 78.96. It is a nonmetal, whose properties are intermediate between those of adjacent chalcogen elements sulfur and tellurium...

 are considered to form organometallic compounds, e.g. organoborane
Organoborane
Organoborane or organoboron compounds are chemical compounds that are organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compounds...

 compounds such as triethylborane
Triethylborane
Triethylborane , also called triethylborine and triethylboron, is an organoborane , a near-colorless to yellowish transparent liquid with pungent ether-like odor. Its chemical formula can be written as C6H15B, or 3B, or 3B, or Et3B.Triethylborane is strongly pyrophoric, igniting spontaneously in...

 (Et3B).

Coordination compounds with organic ligands

Many complex
Complex (chemistry)
In chemistry, a coordination complex or metal complex, is an atom or ion , bonded to a surrounding array of molecules or anions, that are in turn known as ligands or complexing agents...

es feature coordination bonds between a metal and organic ligands. The organic ligands often bind the metal through a heteroatom
Heteroatom
In organic chemistry, a heteroatom is any atom that is not carbon or hydrogen. Usually, the term is used to indicate that non-carbon atoms have replaced carbon in the backbone of the molecular structure...

 such as oxygen or nitrogen, in which case such compounds are considered coordination compounds. However, if any of the ligands form a direct M-C bond, then complex is usually considered to be organometallic, e.g., [(C6H6)Ru(H2O)3]2+. Furthermore, many lipophilic compounds such as metal acetylacetonates and metal alkoxide
Alkoxide
An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO−, where R is the organic substituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands...

s are called "metalorganics."

Many organic coordination compounds occur naturally. For example, hemoglobin
Hemoglobin
Hemoglobin is the iron-containing oxygen-transport metalloprotein in the red blood cells of all vertebrates, with the exception of the fish family Channichthyidae, as well as the tissues of some invertebrates...

 and myoglobin
Myoglobin
Myoglobin is an iron- and oxygen-binding protein found in the muscle tissue of vertebrates in general and in almost all mammals. It is related to hemoglobin, which is the iron- and oxygen-binding protein in blood, specifically in the red blood cells. The only time myoglobin is found in the...

 contain an iron
Iron
Iron is a chemical element with the symbol Fe and atomic number 26. It is a metal in the first transition series. It is the most common element forming the planet Earth as a whole, forming much of Earth's outer and inner core. It is the fourth most common element in the Earth's crust...

 center coordinated to the nitrogen atoms of a porphyrin
Porphyrin
Porphyrins are a group of organic compounds, many naturally occurring. One of the best-known porphyrins is heme, the pigment in red blood cells; heme is a cofactor of the protein hemoglobin. Porphyrins are heterocyclic macrocycles composed of four modified pyrrole subunits interconnected at...

 ring; magnesium
Magnesium
Magnesium is a chemical element with the symbol Mg, atomic number 12, and common oxidation number +2. It is an alkaline earth metal and the eighth most abundant element in the Earth's crust and ninth in the known universe as a whole...

 is the center of a chlorin
Chlorin
In organic chemistry, a chlorin is a large heterocyclic aromatic ring consisting, at the core, of three pyrroles and one pyrroline coupled through four methine linkages...

 ring in chlorophyll
Chlorophyll
Chlorophyll is a green pigment found in almost all plants, algae, and cyanobacteria. Its name is derived from the Greek words χλωρος, chloros and φύλλον, phyllon . Chlorophyll is an extremely important biomolecule, critical in photosynthesis, which allows plants to obtain energy from light...

. The field of such inorganic compound
Inorganic compound
Inorganic compounds have traditionally been considered to be of inanimate, non-biological origin. In contrast, organic compounds have an explicit biological origin. However, over the past century, the classification of inorganic vs organic compounds has become less important to scientists,...

s is known as bioinorganic chemistry
Bioinorganic chemistry
Bioinorganic chemistry is a field that examines the role of metals in biology. Bioinorganic chemistry includes the study of both natural phenomena such as the behavior of metalloproteins as well artificially introduced metals, including those that are non-essential, in medicine and toxicology...

. In contrast to these coordination compounds, methylcobalamin (a form of Vitamin B12
Vitamin B12
Vitamin B12, vitamin B12 or vitamin B-12, also called cobalamin, is a water-soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood. It is one of the eight B vitamins...

), with a cobalt
Cobalt
Cobalt is a chemical element with symbol Co and atomic number 27. It is found naturally only in chemically combined form. The free element, produced by reductive smelting, is a hard, lustrous, silver-gray metal....

-methyl bond, is a true organometallic complex, one of the few known in biology. This subset of complexes are often discussed within the subfield of bioorganometallic chemistry
Bioorganometallic chemistry
Bioorganometallic chemistry is the study of biologically active molecules that contain carbon directly bonded to metals or metalloids. This area straddles the fields of organometallic chemistry, biochemistry, and medicine. It is subset of bioinorganic chemistry. Naturally occurring...

. Illustrative of the many functions of the B12-dependent enzymes, the MTR
5-methyltetrahydrofolate-homocysteine methyltransferase
Methionine synthase also known as MS, MeSe, MetH is an enzyme that in humans is encoded by the MTR gene . This enzyme is responsible for the regeneration of methionine from homocysteine...

 enzyme catalyzes the transfer of a methyl group from a nitrogen on N5-methyl-tetrahydrofolate to the sulfur of homocysteine
Homocysteine
Homocysteine is a non-protein amino acid with the formula HSCH2CH2CHCO2H. It is a homologue of the amino acid cysteine, differing by an additional methylene group. It is biosynthesized from methionine by the removal of its terminal Cε methyl group...

 to produce methionine
Methionine
Methionine is an α-amino acid with the chemical formula HO2CCHCH2CH2SCH3. This essential amino acid is classified as nonpolar. This amino-acid is coded by the codon AUG, also known as the initiation codon, since it indicates mRNA's coding region where translation into protein...

.

The status of compounds in which the canonical anion has a delocalized structure in which the negative charge is shared with an atom more electronegative than carbon, as in enolates, may vary with the nature of the anionic moiety, the metal ion, and possibly the medium; in the absence of direct structural evidence for a carbon–metal bond, such compounds are not considered to be organometallic.

Structure and properties

The metal-carbon bond in organometallic compounds is generally of character intermediate between ionic
Ionic bond
An ionic bond is a type of chemical bond formed through an electrostatic attraction between two oppositely charged ions. Ionic bonds are formed between a cation, which is usually a metal, and an anion, which is usually a nonmetal. Pure ionic bonding cannot exist: all ionic compounds have some...

 and covalent. Primarily ionic metal-carbon bonds are encountered either when the metal is very electropositive
Electronegativity
Electronegativity, symbol χ , is a chemical property that describes the tendency of an atom or a functional group to attract electrons towards itself. An atom's electronegativity is affected by both its atomic number and the distance that its valence electrons reside from the charged nucleus...

 (as in the case of Group 1 or Group 2 metals) or when the carbon-containing ligand exists as a stable carbanion. Carbanions can be stabilized by resonance (as in the case of the aromatic cyclopentadienyl
Cyclopentadienyl
In organic chemistry, cyclopentadienyl is a cyclic group of atoms with the formula C5H5. Cyclopentadienyl are closely related to cyclopentadiene. Cyclopentadienyl have five carbon atoms bonded together in a pentagonal planar ring, all five of which are bonded to individual hydrogen atoms...

 anion) or by the presence of electron-withdrawing substituents (as in the case of the triphenylmethyl anion). Hence, the bonding in compounds like sodium acetylide and triphenylmethylpotassium is primarily ionic. On the other hand, the ionic character of metal-carbon bonds in the organometallic compounds of transition metals, poor metals, and metalloids tends to be intermediate, owing to the middle-of-the-road electronegativity of such metals.

Organometallic compounds with bonds that have characters in between ionic and covalent are very important in industry, as they are both relatively stable in solutions and relatively ionic to undergo reactions. Two important classes are organolithium and Grignard reagents. In certain organometallic compounds such as ferrocene
Ferrocene
Ferrocene is an organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds...

 or dibenzenechromium, the pi orbitals of the organic moiety ligate the metal.

Applications

Organometallics find practical uses in stoichiometric and catalytic processes, especially processes involving carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...

 and alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

-derived polymers. All the world's polyethylene and polypropylene are produced via organometallic catalysts, usually heterogeneously
Heterogeneous catalysis
In chemistry, heterogeneous catalysis refers to the form of catalysis where the phase of the catalyst differs from that of the reactants. Phase here refers not only to solid, liquid, vs gas, but also immiscible liquids, e.g. oil and water. The great majority of practical heterogeneous catalysts...

 via Ziegler-Natta catalysis. Acetic acid is produced via metal carbonyl catalysts in the Monsanto process
Monsanto process
The Monsanto process is an important method for the manufacture of acetic acid by catalytic carbonylation of methanol. This process operates at a pressure of 30–60 atm and a temperature of 150–200 °C and gives a selectivity greater than 99%. It was developed 1960 by German BASF and...

 and Cativa process
Cativa process
The Cativa process is a method for the production of acetic acid by the carbonylation of methanol. The technology, which is similar to the Monsanto process, was developed by BP Chemicals and is under license by BP Plc...

. Most synthetic aldehydes are produced via hydroformylation
Hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond...

. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by hydrogenation
Hydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...

 of hydroformylation derived aldehydes. Similarly, the Wacker process
Wacker process
The Wacker process or the Hoechst-Wacker process originally referred to the oxidation of ethylene to acetaldehyde by oxygen in water in the presence of a tetrachloropalladate catalyst...

 is used in the oxidation of ethylene
Ethylene
Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...

 to acetaldehyde
Acetaldehyde
Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part...

.

Organolithium, organomagnesium, and organoaluminium compounds are highly basic and highly reducing. They catalyze many polymerization reactions, but are also useful stoichiometrically.

III-V semiconductors are produced from trimethylgallium
Trimethylgallium
Trimethylgallium, Ga3, often abbreviated to TMG or TMGa, is the preferred metalorganic source of gallium for metalorganic vapour phase epitaxy of gallium-containing compound semiconductors, such as GaAs, GaN, GaP, GaSb, InGaAs, InGaN, AlGaInP, InGaP and AlInGaNP.-Properties:TMG is a clear,...

, trimethylindium
Trimethylindium
Trimethylindium , In3, is the preferred metalorganic source of Indium for metalorganic vapour phase epitaxy of indium-containing compound semiconductors, such as InP, InAs, InN, InSb, GaInAs, InGaN, AlGaInP, AlInP, AlInGaNP etc. TMI is a white, crystalline and sublimable solid, with melting point...

, trimethylaluminum and related nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...

 / phosphorus
Phosphorus
Phosphorus is the chemical element that has the symbol P and atomic number 15. A multivalent nonmetal of the nitrogen group, phosphorus as a mineral is almost always present in its maximally oxidized state, as inorganic phosphate rocks...

 / arsenic
Arsenic
Arsenic is a chemical element with the symbol As, atomic number 33 and relative atomic mass 74.92. Arsenic occurs in many minerals, usually in conjunction with sulfur and metals, and also as a pure elemental crystal. It was first documented by Albertus Magnus in 1250.Arsenic is a metalloid...

 / antimony
Antimony
Antimony is a toxic chemical element with the symbol Sb and an atomic number of 51. A lustrous grey metalloid, it is found in nature mainly as the sulfide mineral stibnite...

 compounds. These volatile compounds are decomposed along with ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...

, arsine
Arsine
Arsine is the chemical compound with the formula AsH3. This flammable, pyrophoric, and highly toxic gas is one of the simplest compounds of arsenic...

, phosphine
Phosphine
Phosphine is the compound with the chemical formula PH3. It is a colorless, flammable, toxic gas. Pure phosphine is odourless, but technical grade samples have a highly unpleasant odor like garlic or rotting fish, due to the presence of substituted phosphine and diphosphine...

 and related hydrides on a heated substrate via metalorganic vapor phase epitaxy (MOVPE) process for applications such as light emitting diodes (LED
LEd
LEd is a TeX/LaTeX editing software working under Microsoft Windows. It is a freeware product....

s) fabrication.

Organometallic compounds may be found in the environment and some, such as organo-lead and organo mercury compounds are a toxic hazard.

Concepts and techniques

As in other areas of chemistry, electron counting
Electron counting
Electron counting is a formalism used for classifying compounds and for explaining or predicting electronic structure and bonding. Many rules in chemistry rely on electron-counting:...

 is useful for organizing organometallic chemistry. The 18-electron rule
18-Electron rule
The 18-electron rule is a rule of thumb used primarily for predicting formulas for stable metal complexes. The rule rests on the fact that valence shells of a transition metal consists of nine valence orbitals, which collectively can accommodate 18 electrons either as nonbinding electron pairs or...

 is helpful in predicting the stabilities of metal carbonyl
Metal carbonyl
Metal carbonyls are coordination complexes of transition metals with carbon monoxide ligands. These complexes may be homoleptic, that is containing only CO ligands, such as nickel carbonyl , but more commonly metal carbonyls contain a mix of ligands, such as Re3Cl...

s and related compounds. Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the isolobal principle
Isolobal principle
The isolobal principle 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...

.

NMR
NMR spectroscopy
Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is a research technique that exploits the magnetic properties of certain atomic nuclei to determine physical and chemical properties of atoms or the molecules in which they are contained...

 and infrared spectroscopy
Infrared spectroscopy
Infrared spectroscopy is the spectroscopy that deals with the infrared region of the electromagnetic spectrum, that is light with a longer wavelength and lower frequency than visible light. It covers a range of techniques, mostly based on absorption spectroscopy. As with all spectroscopic...

 are common techniques used to determine structure. The dynamic properties of organometallic compounds is often probed with variable-temperature NMR and chemical kinetics.

Organometallic compounds undergo several important reactions:
  • oxidative addition
    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...

     and reductive elimination
  • transmetalation
    Transmetalation
    Transmetalation is a general chemical reaction type in organometallic chemistry describing the exchange of ligands between two metal centers....

  • carbometalation
    Carbometalation
    Carbometalation is an organometallic reaction involving the nucleophilic addition to alkenes and alkynes of a diverse range of organometallic reagents such as organolithium compounds, organocopper compounds and Grignard reagents according to the following general alkyne scheme:The addition can...

  • Hydrometalation
    Hydrometalation
    Hydrometalation is a type of chemical reaction in organometallic chemistry in which a chemical compound with a hydrogen to metal bond adds to a compounds with an unsaturated bond like an alkene forming a new compound with a carbon to metal bond ]]...

  • electron transfer
    Electron transfer
    Electron transfer is the process by which an electron moves from an atom or a chemical species to another atom or chemical species...

  • beta-hydride elimination
    Beta-hydride elimination
    Beta-hydride elimination is a reaction in which an alkyl group bonded to a metal centre is converted into the corresponding metal-bonded hydride and an alkene. The alkyl must have hydrogens on the beta carbon. For instance butyl groups can undergo this reaction but methyl groups cannot...

  • organometallic substitution reaction
  • carbon-hydrogen bond activation
  • cyclometalation
  • Migratory insertion
    Migratory insertion
    A migratory insertion is a type of reaction in organometallic chemistry wherein two ligands on a metal complex combine. It is a subset of reactions that very closely resembles the insertion reactions, and both are differentiated by the mechanism that leads to the resulting stereochemistry of the...


History

Early developments in organometallic chemistry include Louis Claude Cadet
Louis Claude Cadet de Gassicourt
Louis Claude Cadet de Gassicourt was a French chemist who synthesised the first organometalic compound.He obtained a red liquid by the reaction of potassium acetate with arsenic trioxide...

’s synthesis of methyl arsenic compounds related to cacodyl
Cacodyl
Cacodyl, dicacodyl, tetramethyldiarsine, alkarsine or minor part of the "Cadet's fuming liquid" 2As—As2 is a poisonous oily liquid with a garlicky odor...

, William Christopher Zeise
William Christopher Zeise
William Christopher Zeise was a Danish organic chemist. He is best known for the first organometallic compound to be synthesized, named Zeise's salt in his honor. He also discovered the xanthates in 1823....

's platinum-ethylene complex
Zeise's salt
Zeise's salt, potassium trichloroplatinate, is the chemical compound with the formula KPtCl3]·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.-Preparation:This compound is commercially...

, Edward Frankland
Edward Frankland
Sir Edward Frankland, KCB, FRS was a chemist, one of the foremost of his day. He was an expert in water quality and analysis, and originated the concept of combining power, or valence, in chemistry. He was also one of the originators of organometallic chemistry.-Biography:Edward Frankland was born...

’s discovery of dimethyl zinc, Ludwig Mond
Ludwig Mond
Dr Ludwig Mond , was a German-born chemist and industrialist who took British nationality.-Education and career:...

’s discovery of Ni(CO)4, and Victor Grignard
Victor Grignard
François Auguste Victor Grignard was a Nobel Prize-winning French chemist.Grignard was the son of a sail maker. After studying mathematics at Lyon he transferred to chemistry and discovered the synthetic reaction bearing his name in 1900...

’s organomagnesium compounds. The abundant and diverse products from coal and petroleum led to Ziegler-Natta, Fischer-Tropsch, hydroformylation
Hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond...

 catalysis which employ CO, H2, and alkenes as feedstocks and ligands.

Tetraethyllead previously was combined with gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...

 as an antiknock agent
Antiknock agent
An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuel's octane rating.The mixture known as gasoline, when used in high compression internal combustion engines, has a tendency to ignite early causing a damaging "engine knocking" noise...

. Due to lead's toxicity it is no longer used, its replacements being other organometallic compounds such as ferrocene
Ferrocene
Ferrocene is an organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds...

 and methylcyclopentadienyl manganese tricarbonyl
Methylcyclopentadienyl manganese tricarbonyl
Methylcyclopentadienyl manganese tricarbonyl is an organomanganese compound with the formula Mn3. Marketed initially in 1958 as a supplement to the gasoline additive tetraethyl lead to increase the fuel's octane rating, MMT was later used in unleaded gasoline...

 (MMT).

Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to Ernst Fischer
Ernst Otto Fischer
Ernst Otto Fischer was a German chemist who won the Nobel Prize for pioneering work in the area of organometallic chemistry.-Early life:...

 and Geoffrey Wilkinson
Geoffrey Wilkinson
Sir Geoffrey Wilkinson FRS was a Nobel laureate English chemist who pioneered inorganic chemistry and homogeneous transition metal catalysis.-Biography:...

 for work on metallocene
Metallocene
A metallocene is a compound typically consisting of two cyclopentadienyl anions bound to a metal center in the oxidation state II, with the resulting general formula 2M. Closely related to the metallocenes are the metallocene derivatives, e.g. titanocene dichloride, vanadocene dichloride...

s. In 2005, Yves Chauvin
Yves Chauvin
Yves Chauvin is a French chemist and Nobel Prize laureate. He is honorary research director at the Institut français du pétrole and a member of the French Academy of Science. Chauvin received his degree from the Lyon School of Chemistry, Physics and Electronics in 1954.He was awarded the 2005...

, Robert H. Grubbs
Robert H. Grubbs
Robert Howard Grubbs is an American chemist and Nobel laureate.As he noted in his official Nobel Prize autobiography, "In some places, my birthplace is listed as Calvert City and in others Possum Trot [NB: both in Marshall County]...

 and Richard R. Schrock
Richard R. Schrock
Richard Royce Schrock is an American chemist and Nobel laureate recognized for his contributions to the metathesis reaction used in organic chemistry.-Biography:...

 shared the Nobel Prize for metal-catalyzed olefin metathesis
Olefin metathesis
Olefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R...

.

Organometallic chemistry timeline

  • 1760 Louis Claude Cadet de Gassicourt
    Louis Claude Cadet de Gassicourt
    Louis Claude Cadet de Gassicourt was a French chemist who synthesised the first organometalic compound.He obtained a red liquid by the reaction of potassium acetate with arsenic trioxide...

     investigates inks based on Cobalt
    Cobalt
    Cobalt is a chemical element with symbol Co and atomic number 27. It is found naturally only in chemically combined form. The free element, produced by reductive smelting, is a hard, lustrous, silver-gray metal....

     salts and isolates Cacodyl
    Cacodyl
    Cacodyl, dicacodyl, tetramethyldiarsine, alkarsine or minor part of the "Cadet's fuming liquid" 2As—As2 is a poisonous oily liquid with a garlicky odor...

     from cobalt mineral containing arsenic
    Arsenic
    Arsenic is a chemical element with the symbol As, atomic number 33 and relative atomic mass 74.92. Arsenic occurs in many minerals, usually in conjunction with sulfur and metals, and also as a pure elemental crystal. It was first documented by Albertus Magnus in 1250.Arsenic is a metalloid...

  • 1827 Zeise's salt
    Zeise's salt
    Zeise's salt, potassium trichloroplatinate, is the chemical compound with the formula KPtCl3]·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.-Preparation:This compound is commercially...

     is the first platinum
    Platinum
    Platinum is a chemical element with the chemical symbol Pt and an atomic number of 78. Its name is derived from the Spanish term platina del Pinto, which is literally translated into "little silver of the Pinto River." It is a dense, malleable, ductile, precious, gray-white transition metal...

     / olefin complex
  • 1848 Edward Frankland
    Edward Frankland
    Sir Edward Frankland, KCB, FRS was a chemist, one of the foremost of his day. He was an expert in water quality and analysis, and originated the concept of combining power, or valence, in chemistry. He was also one of the originators of organometallic chemistry.-Biography:Edward Frankland was born...

     discovers diethylzinc
    Diethylzinc
    Diethylzinc 2Zn, or DEZn, is a highly pyrophoric organozinc compound consisting of a zinc center bound to two ethyl groups. This colourless liquid is an important reagent in organic chemistry and available commercially as a solution in hexanes, heptane, or toluene.-Synthesis:Edward Frankland first...

  • 1863 Charles Friedel
    Charles Friedel
    Charles Friedel was a French chemist and mineralogist. A native of Strasbourg, France, he was a student of Louis Pasteur at the Sorbonne...

     and James Crafts
    James Crafts
    James Mason Crafts was an American chemist, best known for developing the Friedel-Crafts alkylation and acylation reactions with Charles Friedel in 1876.-Biography:...

     prepare organochlorosilanes
  • 1890 Ludwig Mond
    Ludwig Mond
    Dr Ludwig Mond , was a German-born chemist and industrialist who took British nationality.-Education and career:...

     discovers Nickel carbonyl
    Nickel carbonyl
    Nickel carbonyl is the organonickel compound with the formula Ni4. This pale-yellow liquid is the principal carbonyl of nickel. It is an intermediate in the Mond process for the purification of nickel and a reagent in organometallic chemistry...

  • 1899 Introduction of Grignard reaction
    Grignard reaction
    The Grignard reaction is an organometallic chemical reaction in which alkyl- or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is an important tool for the formation of carbon–carbon bonds...

  • 1900 Paul Sabatier
    Paul Sabatier (chemist)
    Paul Sabatier FRS was a French chemist, born at Carcassonne. He taught science classes most of his life before he became Dean of the Faculty of Science at the University of Toulouse in 1905....

     works on hydrogenation
    Hydrogenation
    Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...

     organic compounds with metal catalysts. Hydrogenation of fat
    Fat
    Fats consist of a wide group of compounds that are generally soluble in organic solvents and generally insoluble in water. Chemically, fats are triglycerides, triesters of glycerol and any of several fatty acids. Fats may be either solid or liquid at room temperature, depending on their structure...

    s kicks off advances in food industry
    Food industry
    The food production is a complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population...

    , see margarine
    Margarine
    Margarine , as a generic term, can indicate any of a wide range of butter substitutes, typically composed of vegetable oils. In many parts of the world, the market share of margarine and spreads has overtaken that of butter...

  • 1909 Paul Ehrlich
    Paul Ehrlich
    Paul Ehrlich was a German scientist in the fields of hematology, immunology, and chemotherapy, and Nobel laureate. He is noted for curing syphilis and for his research in autoimmunity, calling it "horror autotoxicus"...

     introduces Salvarsan for the treatment of syphilis, an early arsenic based organometallic compound
  • 1912 Nobel Prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     Victor Grignard
    Victor Grignard
    François Auguste Victor Grignard was a Nobel Prize-winning French chemist.Grignard was the son of a sail maker. After studying mathematics at Lyon he transferred to chemistry and discovered the synthetic reaction bearing his name in 1900...

     and Paul Sabatier
    Paul Sabatier (chemist)
    Paul Sabatier FRS was a French chemist, born at Carcassonne. He taught science classes most of his life before he became Dean of the Faculty of Science at the University of Toulouse in 1905....

  • 1930 Henry Gilman
    Henry Gilman
    Henry Gilman was an American organic chemist known as the father of organometallic chemistry, the field within which his most notable work was done. He discovered the Gilman reagent, which bears his name....

     works on lithium cuprates, see Gilman reagent
    Gilman reagent
    A Gilman reagent is a lithium and copper reagent compound, R2CuLi, where R is an organic radical. These are useful because they react with organic chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller...

  • 1951 Ferrocene
    Ferrocene
    Ferrocene is an organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemical compound consisting of two cyclopentadienyl rings bound on opposite sides of a central metal atom. Such organometallic compounds are also known as sandwich compounds...

     is discovered
  • 1963 Nobel prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     for Karl Ziegler
    Karl Ziegler
    Karl Waldemar Ziegler was a German chemist who won the Nobel Prize in Chemistry in 1963, with Giulio Natta, for work on polymers. The Nobel Committee recognized his "excellent work on organometallic compounds [which]...led to new polymerization reactions and ... paved the way for new and highly...

     and Giulio Natta
    Giulio Natta
    Giulio Natta was an Italian chemist and Nobel laureate. He won a Nobel Prize in Chemistry in 1963 with Karl Ziegler for work on high polymers.-Early years:...

     on Ziegler-Natta catalyst
    Ziegler-Natta catalyst
    A Ziegler–Natta catalyst is a catalyst used in the synthesis of polymers of 1-alkenes . Three types of Ziegler–Natta catalysts are currently employed:* Solid and supported catalysts based on titanium compounds...

  • 1965 Discovery of cyclobutadieneiron tricarbonyl
    Cyclobutadieneiron tricarbonyl
    Cyclobutadieneiron tricarbonyl or Fe3 is an organometallic complex of cyclobutadiene and an iron metal carbonyl. The chemical compound is used in organic chemistry as a precursor for cyclobutadiene...

  • 1968 Heck reaction
    Heck reaction
    The Heck reaction is the chemical reaction of an unsaturated halide with an alkene and a base and palladium catalyst to form a substituted alkene. Together with the other palladium-catalyzed cross-coupling reactions, this reaction is of great importance, as it allows one to do substitution...

  • 1973 Nobel prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     Geoffrey Wilkinson
    Geoffrey Wilkinson
    Sir Geoffrey Wilkinson FRS was a Nobel laureate English chemist who pioneered inorganic chemistry and homogeneous transition metal catalysis.-Biography:...

     and Ernst Otto Fischer
    Ernst Otto Fischer
    Ernst Otto Fischer was a German chemist who won the Nobel Prize for pioneering work in the area of organometallic chemistry.-Early life:...

     on sandwich compound
    Sandwich compound
    In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands. The arenes have the formula CnHn, substituted derivatives and heterocyclic derivatives...

    s
  • 1981 Nobel prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     Roald Hoffman and Kenichi Fukui
    Kenichi Fukui
    Kenichi Fukui was a Japanese chemist.Kenichi Fukui was co-recipient of the Nobel Prize in Chemistry in 1981 with Roald Hoffmann, for their independent investigations into the mechanisms of chemical reactions...

     on Isolobal Principle
    Isolobal principle
    The isolobal principle 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...

  • 2005 Nobel prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     Yves Chauvin
    Yves Chauvin
    Yves Chauvin is a French chemist and Nobel Prize laureate. He is honorary research director at the Institut français du pétrole and a member of the French Academy of Science. Chauvin received his degree from the Lyon School of Chemistry, Physics and Electronics in 1954.He was awarded the 2005...

    , Robert Grubbs, and Richard Schrock on metal-catalyzed alkene metathesis
    Olefin metathesis
    Olefin metathesis or transalkylidenation is an organic reaction that entails redistribution of alkylene fragments by the scission of carbon - carbon double bonds in olefins . Its advantages include the creation of fewer sideproducts and hazardous wastes. Yves Chauvin, Robert H. Grubbs, and Richard R...

  • 2010 Nobel prize
    Nobel Prize in Chemistry
    The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, physics, literature,...

     Richard F. Heck
    Richard F. Heck
    Richard Fred Heck is an American chemist noted for the discovery and development of the Heck reaction, which uses palladium to catalyze organic chemical reactions that couple aryl halides with alkenes....

    , Ei-ichi Negishi
    Ei-ichi Negishi
    is a Japanese chemist who has spent most of his career at Purdue University, United States. He is best known for his discovery of the Negishi coupling. He was awarded the 2010 Nobel Prize in Chemistry "for palladium catalyzed cross couplings in organic synthesis" jointly with Richard F. Heck and...

    , Akira Suzuki
    Akira Suzuki (chemist)
    is a Japanese chemist and Nobel Prize Laureate , who first published the Suzuki reaction, the organic reaction of an aryl- or vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by a palladium complex, in 1979.-Life:...


Organometallics

  • Period 2 element
    Period 2 element
    A period 2 element is one of the chemical elements in the second row of the periodic table. The periodic table is laid out in rows to illustrate recurring trends in the chemical behavior of the elements as their atomic number increases; a new row is started when chemical behavior begins to...

    s: organolithium chemistry, organoberyllium chemistry, organoborane chemistry,
  • Period 3 element
    Period 3 element
    A period 3 element is one of the chemical elements in the third row of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring trends in the chemical behaviour of the elements as their atomic number increases: a new row is begun when chemical...

    s: organomagnesium chemistry, organoaluminum chemistry, organosilicon chemistry
    Organosilicon
    Organosilicon compounds are organic compounds containing carbon silicon bonds. Organosilicon chemistry is the corresponding science exploring their properties and reactivity.Like carbon, the organically bound silicon is tetravalent and tetrahedral...

  • Period 4 element
    Period 4 element
    A period 4 element is one of the chemical elements in the fourth row of the periodic table of the elements. The periodic table is laid out in rows to illustrate recurring trends in the chemical behaviour of the elements as their atomic number increases: a new row is begun when chemical behaviour...

    s: organotitanium chemistry, organochromium chemistry
    Organochromium chemistry
    Organochromium chemistry is a branch of organometallic chemistry that deals with organic compounds containing a chromium to carbon bond and their reactions. The field is of some relevance to organic synthesis. The relevant oxidation states for chromium range from -2 to +6.-History:The first...

    , organomanganese chemistry
    Organomanganese chemistry
    Organomanganese chemistry is the chemistry of organometallic compounds containing a carbon to manganese chemical bond. In a recent review Cahiez et al...

     organoiron chemistry
    Organoiron chemistry
    Organoiron chemistry is the chemistry of organometallic compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. Iron adopts oxidation states from Fe...

    , organocobalt chemistry
    Organocobalt chemistry
    Organocobalt chemistry is the chemistry of organometallic compounds containing a carbon to cobalt chemical bond. Organocobalt compounds are involved in several organic reactions and the important biomolecule vitamin B12 has a cobalt-carbon bond. Many organocobalt compounds are investigated for...

     organonickel chemistry, organocopper chemistry, organozinc chemistry, organogallium chemistry
    Organogallium chemistry
    Organogallium chemistry is the chemistry of organometallic compounds containing a carbon to gallium chemical bond. Despite their high toxicity organogallium compounds have some use in organic synthesis. The compound trimethylgallium is of some relevance to MOCVD as a precursor to gallium...

    , organogermanium chemistry
  • Period 5 element
    Period 5 element
    A period 5 element is one of the chemical elements in the fifth row of the periodic table of the elements. The periodic table is laid out in rows to illustrate recurring trends in the chemical behaviour of the elements as their atomic number increases: a new row is begun when chemical behaviour...

    s: organoruthenium chemistry
    Organoruthenium chemistry
    Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. The interest is mostly academic although several organoruthenium catalysts are of commercial interest. The chemistry has many similarities with organoiron chemistry, as iron is...

    . organopalladium chemistry, organosilver chemistry
    Organosilver chemistry
    Organosilver chemistry in chemistry is the study of organometallic compounds containing a carbon to silver chemical bond and the study of silver as catalyst in organic reactions. In the group 11 elements silver is the element below copper...

    , organocadmium chemistry, organoindium chemistry, organotin chemistry
  • Period 6 element
    Period 6 element
    A period 6 element is one of the chemical elements in the sixth row of the periodic table of the elements, including the lanthanides...

    s: organolanthanide chemistry
    Organolanthanide chemistry
    Organolanthanide chemistry is the field of chemistry that studies compounds with a lanthanide-to-carbon bond.-Background:With the exception of lutetium, all lanthanides belong to the f block...

    , organoosmium chemistry, organoiridium chemistry, organoplatinum chemistry, organogold chemistry
    Organogold chemistry
    Organogold chemistry is the study of compounds containing carbon-gold bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN...

    , organomercury chemistry
    Organomercury
    Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg-C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury cation, CH3Hg+; ethylmercury cation, C2H5Hg+; dimethylmercury, 2Hg,...

    , organothallium chemistry, organolead chemistry

See also

  • Chelation
    Chelation
    Chelation is the formation or presence of two or more separate coordinate bonds between apolydentate ligand and a single central atom....

  • Bioorganometallic chemistry
    Bioorganometallic chemistry
    Bioorganometallic chemistry is the study of biologically active molecules that contain carbon directly bonded to metals or metalloids. This area straddles the fields of organometallic chemistry, biochemistry, and medicine. It is subset of bioinorganic chemistry. Naturally occurring...

  • Green-Davies-Mingos rules
    Green-Davies-Mingos rules
    In organometallic chemistry, the Green–Davies–Mingos rules predict the regiochemistry for nucleophilic addition to 18-electron metal complexes containing multiple unsaturated ligands. In general, complexation enhances the susceptibility of unsaturated hydrocarbon toward nucleophilic attack.*Rule 1...


  • Compounds of carbon with other elements in the periodic table:


External links

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