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Organometallic chemistry is the study of organometallic compounds,
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
s containing at least one
chemical bond A chemical bond is the association of atoms or ions to form molecules, crystals, and other structures. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds or through the sharing of electrons a ...
between a
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
atom of an
organic molecule Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-cont ...
and 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 ...
, including
alkali In chemistry, an alkali (; from the Arabic word , ) is a basic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a soluble base has a pH greater than 7.0. The a ...
, alkaline earth, and
transition metals In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. The lanthanide and actinid ...
, and sometimes broadened to include
metalloids A metalloid is a chemical element which has a preponderance of properties in between, or that are a mixture of, those of metals and nonmetals. The word metalloid comes from the Latin ''metallum'' ("metal") and the Greek ''oeides'' ("resembling ...
like boron, silicon, and selenium, as well. Aside from bonds to
organyl In organic and organometallic chemistry, an organyl group (commonly denoted by the letter " R") is an organic substituent with one (sometimes more) free valence electron(s) at a carbon atom.. The term is often used in chemical patent literatur ...
fragments or molecules, bonds to 'inorganic' carbon, like
carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...
( metal carbonyls),
cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...
, or
carbide In chemistry, a carbide usually describes a compound composed of carbon and a metal. In metallurgy, carbiding or carburizing is the process for producing carbide coatings on a metal piece. Interstitial / Metallic carbides The carbides of th ...
, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term " metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates,
alkoxide In chemistry, an alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as , where R is the organyl substituent. Alkoxides are strong bases and, whe ...
s, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional
inorganic An inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds⁠that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as '' inorganic chemistry''. Inor ...
and
organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
. 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 In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst in a solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in d ...
), where target molecules include polymers, pharmaceuticals, and many other types of practical products.


Organometallic compounds

Organometallic compounds are distinguished by the prefix "organo-" (e.g., organopalladium compounds), and include all compounds which contain a bond between a metal atom and a carbon atom of an
organyl group In organic and organometallic chemistry, an organyl group (commonly denoted by the letter " R") is an organic substituent with one (sometimes more) free valence electron(s) at a carbon atom.. The term is often used in chemical patent literatur ...
. In addition to the traditional metals (
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...
s, alkali earth metals,
transition metals In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. The lanthanide and actinid ...
, and post transition metals),
lanthanide The lanthanide () or lanthanoid () series of chemical elements comprises at least the 14 metallic chemical elements with atomic numbers 57–70, from lanthanum through ytterbium. In the periodic table, they fill the 4f orbitals. Lutetium (el ...
s,
actinide The actinide () or actinoid () series encompasses at least the 14 metallic chemical elements in the 5f series, with atomic numbers from 89 to 102, actinium through nobelium. Number 103, lawrencium, is also generally included despite being part ...
s, semimetals, and the elements
boron Boron is a chemical element; it has symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the boron group it has three ...
,
silicon Silicon is a chemical element; it has symbol Si and atomic number 14. It is a hard, brittle crystalline solid with a blue-grey metallic lustre, and is a tetravalent metalloid (sometimes considered a non-metal) and semiconductor. It is a membe ...
,
arsenic Arsenic is a chemical element; it has Symbol (chemistry), symbol As and atomic number 33. It is a metalloid and one of the pnictogens, and therefore shares many properties with its group 15 neighbors phosphorus and antimony. Arsenic is not ...
, and
selenium Selenium is a chemical element; it has symbol (chemistry), symbol Se and atomic number 34. It has various physical appearances, including a brick-red powder, a vitreous black solid, and a grey metallic-looking form. It seldom occurs in this elem ...
are considered to form organometallic compounds. Examples of organometallic compounds include
Gilman reagent A Gilman reagent is a diorganocopper compound with the formula Li uR2 where R is an alkyl or aryl. They are colorless solids. Use in organic chemistry These reagents are useful because, unlike related Grignard reagents and organolithium reage ...
s, which contain
lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...
and
copper Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...
, and
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, which contain
magnesium Magnesium is a chemical element; it has Symbol (chemistry), symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 ...
. Boron-containing organometallic compounds are often the result of hydroboration and carboboration reactions. Tetracarbonyl nickel and
ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
are examples of organometallic compounds containing
transition metal In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. The lanthanide and actinid ...
s. Other examples of organometallic compounds include organolithium compounds such as ''n''-butyllithium (n-BuLi), organozinc compounds such as diethylzinc (Et2Zn),
organotin Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
compounds such as
tributyltin hydride Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis. Synthesis and characterization The c ...
(Bu3SnH), organoborane compounds such as triethylborane (Et3B), and
organoaluminium Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monom ...
compounds such as
trimethylaluminium Trimethylaluminium or TMA is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula (abbreviated as , where Me stands for methyl), as it exists as a dimer. This colorless liquid is pyrophoric. It is an ...
(Me3Al). A naturally occurring organometallic complex is
methylcobalamin Methylcobalamin (mecobalamin, MeCbl, or MeB) is a cobalamin, a form of vitamin B12, vitamin B. It differs from cyanocobalamin in that the cyanide, cyano group at the cobalt is replaced with a methyl group. Methylcobalamin features an octahedral ...
(a form of Vitamin B12), which contains a
cobalt Cobalt is a chemical element; it has Symbol (chemistry), symbol Co and atomic number 27. As with nickel, cobalt is found in the Earth's crust only in a chemically combined form, save for small deposits found in alloys of natural meteoric iron. ...
-
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
bond. This complex, along with other biologically relevant complexes are often discussed within the subfield of bioorganometallic chemistry. File:Ferrocene.svg,
Ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
is an archetypal organoiron complex. It is an air-stable, sublimable compound. File:Cobaltocene.svg,
Cobaltocene Cobaltocene, known also as bis(cyclopentadienyl)cobalt(II) or even "bis Cp cobalt", is an organocobalt compound with the formula Co(C5H5)2. It is a dark purple solid that sublimes readily slightly above room temperature. Cobaltocene was discover ...
is a structural analogue of ferrocene, but is highly reactive toward air. File:HRh(CO)P3again.png, Tris(triphenylphosphine)rhodium carbonyl hydride is used in the commercial production of many aldehyde-based
fragrance An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...
s. File:Zeise'sSalt.png, Zeise's salt is an example of a transition metal alkene complex. File:Trimethylaluminium-from-xtal-3D-bs-17.png,
Trimethylaluminium Trimethylaluminium or TMA is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula (abbreviated as , where Me stands for methyl), as it exists as a dimer. This colorless liquid is pyrophoric. It is an ...
is an organometallic compound with a bridging
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...
. It is used in the industrial production of some alcohols. File:Dimethylzinc-3D-balls.png, Dimethylzinc has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films. File:Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png, Lithium diphenylcuprate bis(diethyl etherate) is an example of a
Gilman reagent A Gilman reagent is a diorganocopper compound with the formula Li uR2 where R is an alkyl or aryl. They are colorless solids. Use in organic chemistry These reagents are useful because, unlike related Grignard reagents and organolithium reage ...
, a type of organocopper complex frequently employed in organic synthesis. File:AdoCbl-ColorCoded.png,
Adenosylcobalamin Adenosylcobalamin (AdoCbl), also known as coenzyme B12, cobamamide, and dibencozide, is one of the biologically active forms of vitamin B12. Adenosylcobalamin participates as a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. T ...
is a cofactor required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology. File:IronPentacarbonylStructure.png, Iron(0) pentacarbonyl is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure. File:Tc99 sestamibi 2D structure.svg, Technetium sup>99mTcsestamibi is used to image the heart muscle in nuclear medicine.


Distinction from coordination compounds with organic ligands

Many
complex Complex commonly refers to: * Complexity, the behaviour of a system whose components interact in multiple ways so possible interactions are difficult to describe ** Complex system, a system composed of many components which may interact with each ...
es feature coordination bonds between a metal and organic
ligands 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 ...
. Complexes where the organic ligands bind the metal through a
heteroatom In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen. Organic chemistry In practice, the term is mainly used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecular ...
such as oxygen or nitrogen are considered coordination compounds (e.g., heme A and Fe(acac)3). However, if any of the ligands form a direct metal-carbon (M-C) bond, then the complex is considered to be organometallic. Although the IUPAC has not formally defined the term, some chemists use the term "metalorganic" to describe any coordination compound containing an organic ligand regardless of the presence of a direct M-C bond. The status of compounds in which the canonical anion has a negative charge that is shared between (
delocalized In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.IUPAC Gold Boo''delocalization''/ref> The term delocalization is general and can have slightly dif ...
) a carbon atom and an atom more
electronegative Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the d ...
than carbon (e.g.
enolate In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl () compounds. Rarely isolated, they are widely used as reagents in the Organic synthesis, synthesis of organic compounds. Bonding and structure Enolate ...
s) 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. For instance, lithium enolates often contain only Li-O bonds and are not organometallic, while zinc enolates ( Reformatsky reagents) contain both Zn-O and Zn-C bonds, and are organometallic in nature.


Structure and properties

The metal-carbon bond in organometallic compounds is generally highly
covalent A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atom ...
. For highly electropositive elements, such as lithium and sodium, the carbon ligand exhibits
carbanion In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge. Formally, a carbanion is the conjugate base of a carbon acid: : where B stands for the base (chemist ...
ic character, but free carbon-based anions are extremely rare, an example being
cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...
. Most organometallic compounds are solids at room temperature, however some are liquids such as methylcyclopentadienyl manganese tricarbonyl, or even volatile liquids such as nickel tetracarbonyl. Many organometallic compounds are
air sensitive Air sensitivity is a term used, particularly in chemistry, to denote the reactivity of chemical compounds with some constituent of air. Most often, reactions occur with atmospheric oxygen (O2) or water vapor (H2O), although reactions with the other ...
(reactive towards oxygen and moisture), and thus they must be handled under an inert atmosphere. Some organometallic compounds such as
triethylaluminium Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name the compound has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA). This colorless liquid is pyrophoric. It is an industrially important comp ...
are
pyrophoric A substance is pyrophoric (from , , 'fire-bearing') if it ignites spontaneously in air at or below (for gases) or within 5 minutes after coming into contact with air (for liquids and solids). Examples are organolithium compounds and triethylb ...
and will ignite on contact with air.


Concepts and techniques

As in other areas of chemistry,
electron counting In chemistry, electron counting is a formalism for assigning a number of valence electrons to individual atoms in a molecule. It is used for classifying compounds and for explaining or predicting their electronic structure and chemical bond, bondi ...
is useful for organizing organometallic chemistry. The 18-electron rule is helpful in predicting the stabilities of organometallic complexes, for example
metal carbonyl A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. These properties are all associated with having electrons available at the Fermi level, as against n ...
s and
metal hydrides In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and has been more frequently in the past) applied to all co ...
. The 18e rule has two representative electron counting models, ionic and neutral (also known as covalent) ligand models, respectively. The hapticity of a metal-ligand complex, can influence the electron count.
Hapticity In coordination chemistry, hapticity is the coordination complex, coordination of a ligand to a metal center via an uninterrupted and contiguous series of atoms. The hapticity of a ligand is described with the Greek letter eta (letter), η ('eta ...
(η, lowercase Greek eta), describes the number of contiguous ligands coordinated to a metal. For example,
ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
, η5-C5H5)2Fe has two cyclopentadienyl ligands giving a hapticity of 5, where all five carbon atoms of the C5H5 ligand bond equally and contribute one electron to the iron center. Ligands that bind non-contiguous atoms are denoted the Greek letter kappa, κ.
Chelating Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...
κ2-acetate is an example. The covalent bond classification method identifies three classes of ligands, X,L, and Z; which are based on the electron donating interactions of the ligand. Many organometallic compounds do not follow the 18e rule. The metal atoms in organometallic compounds are frequently described by their
d electron count The d electron count or number of d electrons is a chemistry formalism used to describe the electron configuration of the valence electrons of a transition metal center in a coordination complex. The d electron count is an effective way to unders ...
and
oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical Electrical charge, charge of an atom if all of its Chemical bond, bonds to other atoms are fully Ionic bond, ionic. It describes the degree of oxidation (loss of electrons ...
. These concepts can be used to help predict their reactivity and preferred
geometry Geometry (; ) is a branch of mathematics concerned with properties of space such as the distance, shape, size, and relative position of figures. Geometry is, along with arithmetic, one of the oldest branches of mathematics. A mathematician w ...
. Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the
isolobal principle In organometallic chemistry, the isolobal principle (more formally known as the isolobal analogy) is a strategy used to relate the structure of organic and inorganic molecular fragments in order to predict bonding properties of organometallic co ...
. A wide variety of physical techniques are used to determine the structure, composition, and properties of organometallic compounds.
X-ray diffraction X-ray diffraction is a generic term for phenomena associated with changes in the direction of X-ray beams due to interactions with the electrons around atoms. It occurs due to elastic scattering, when there is no change in the energy of the waves. ...
is a particularly important technique that can locate the positions of atoms within a solid compound, providing a detailed description of its structure. Other techniques like
infrared spectroscopy Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) is the measurement of the interaction of infrared radiation with matter by absorption, emission, or reflection. It is used to study and identify chemical substances or functio ...
and
nuclear magnetic resonance spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a Spectroscopy, spectroscopic technique based on re-orientation of Atomic nucleus, atomic nuclei with non-zero nuclear sp ...
are also frequently used to obtain information on the structure and bonding of organometallic compounds. Ultraviolet-visible spectroscopy is a common technique used to obtain information on the electronic structure of organometallic compounds. It is also used monitor the progress of organometallic reactions, as well as determine their kinetics. The dynamics of organometallic compounds can be studied using dynamic NMR spectroscopy. Other notable techniques include X-ray absorption spectroscopy, electron paramagnetic resonance spectroscopy, and
elemental analysis Elemental analysis is a process where a sample of some material (e.g., soil, waste or drinking water, bodily fluids, minerals, chemical compounds) is analyzed for its elemental and sometimes isotopic composition. Elemental analysis can be qualita ...
. Due to their high reactivity towards oxygen and moisture, organometallic compounds often must be handled using
air-free techniques Air-free techniques refer to a range of manipulations in the chemistry laboratory for the handling of Compound (chemistry), compounds that are air-sensitive. These techniques prevent the compounds from reacting with components of air, usually water ...
. Air-free handling of organometallic compounds typically requires the use of laboratory apparatuses such as a
glovebox A glovebox (or glove box) is a sealed container that is designed to allow one to manipulate objects where a separate atmosphere is desired. Built into the sides of the glovebox are gloves arranged in such a way that the user can place their hand ...
or Schlenk line.


History

Early developments in organometallic chemistry include Louis Claude Cadet's synthesis of methyl arsenic compounds related to
cacodyl Cacodyl, also known as dicacodyl or tetramethyldiarsine, (CH3)2As–As(CH3)2, is an organoarsenic compound that constitutes a major part of " Cadet's fuming liquid" (named after the French chemist Louis Claude Cadet de Gassicourt). It is a poisono ...
,
William Christopher Zeise William Christopher Zeise (15 October 1789 – 12 November 1847) was a Danish organic chemist. He is best known for synthesising one of the first organometallic compounds, named Zeise's salt in his honour. He also performed pioneering studie ...
'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. (Although not always acknowledged as an organometallic compound,
Prussian blue Prussian blue (also known as Berlin blue, Brandenburg blue, Parisian and Paris blue) is a dark blue pigment produced by oxidation of ferrous ferrocyanide salts. It has the chemical formula . It consists of cations, where iron is in the oxidat ...
, a mixed-valence iron-cyanide complex, was first prepared in 1706 by paint maker Johann Jacob Diesbach as the first
coordination polymer Coordination may refer to: * Coordination (linguistics), a compound grammatical construction * Coordination complex, consisting of a central atom or ion and a surrounding array of bound molecules or ions ** A chemical reaction to form a coordinat ...
and synthetic material containing a metal-carbon bond.) The abundant and diverse products from coal and petroleum led to Ziegler–Natta, Fischer–Tropsch,
hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
catalysis which employ CO, H2, and alkenes as feedstocks and ligands. Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to Ernst Fischer and
Geoffrey Wilkinson Sir Geoffrey Wilkinson FRS (14 July 1921 – 26 September 1996) was a Nobel laureate English chemist who pioneered inorganic chemistry and homogeneous transition metal catalysis. Education and early life Wilkinson was born at Springside, Todm ...
for work on
metallocene A metallocene is a compound typically consisting of two cyclopentadienyl anions (, abbreviated Cp) bound to a metallic element, metal center (M) in the oxidation state II, with the resulting general formula Closely related to the metallocenes are ...
s. In 2005, Yves Chauvin, Robert H. Grubbs and Richard R. Schrock shared the Nobel Prize for metal-catalyzed olefin metathesis.


Organometallic chemistry timeline

* 1760 Louis Claude Cadet de Gassicourt isolates the
organoarsenic compound Organoarsenic chemistry is the chemistry of Chemical compound, compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herb ...
cacodyl Cacodyl, also known as dicacodyl or tetramethyldiarsine, (CH3)2As–As(CH3)2, is an organoarsenic compound that constitutes a major part of " Cadet's fuming liquid" (named after the French chemist Louis Claude Cadet de Gassicourt). It is a poisono ...
* 1827
William Christopher Zeise William Christopher Zeise (15 October 1789 – 12 November 1847) was a Danish organic chemist. He is best known for synthesising one of the first organometallic compounds, named Zeise's salt in his honour. He also performed pioneering studie ...
produces Zeise's salt; the first
platinum Platinum is a chemical element; it has Symbol (chemistry), symbol Pt and atomic number 78. It is a density, dense, malleable, ductility, ductile, highly unreactive, precious metal, precious, silverish-white transition metal. Its name origina ...
/
olefin 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 ...
complex * 1848 Edward Frankland discovers diethylzinc * 1890 Ludwig Mond discovers
nickel carbonyl Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a Organonickel chemistry, nickel(0) organometallic compound with the chemical formula, formula Ni(CO)4. This colorless liquid is the principal metal carbonyl, carbonyl of nickel. It is an React ...
* 1899 John Ulric Nef discovers alkynylation using sodium
acetylide In chemistry, an acetylide is a compound that can be viewed as the result of replacing one or both hydrogen atoms of acetylene (ethyne) by metallic or other cations. Calcium carbide is an important industrial compound, which has long been used ...
s. * 1909
Paul Ehrlich Paul Ehrlich (; 14 March 1854 – 20 August 1915) was a Nobel Prize-winning German physician and scientist who worked in the fields of hematology, immunology and antimicrobial chemotherapy. Among his foremost achievements were finding a cure fo ...
introduces
Salvarsan Arsphenamine, also known as Salvarsan or compound 606, is an antibiotic drug that was introduced at the beginning of the 1910s as the first effective treatment for the deadly infectious diseases syphilis, relapsing fever, and African trypanosomias ...
for the treatment of syphilis, an early arsenic based organometallic compound * 1912
Nobel Prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
Victor Grignard and Paul Sabatier * 1930 Henry Gilman invents lithium cuprates, see
Gilman reagent A Gilman reagent is a diorganocopper compound with the formula Li uR2 where R is an alkyl or aryl. They are colorless solids. Use in organic chemistry These reagents are useful because, unlike related Grignard reagents and organolithium reage ...
* 1940 Eugene G. Rochow and Richard Müller discover the direct process for preparing
organosilicon Organosilicon chemistry is the study of organometallic compounds containing carbon–silicon bonds, to which they are called organosilicon compounds. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, f ...
compounds * 1930's and 1940's
Otto Roelen Otto Roelen (22 March 1897 – 30 January 1993) was a German chemist who pioneered using carbon monoxide to synthesize of organic compounds. Roelen was born in Mülheim, Germany and studied chemistry and graduated in 1922 from Technische Hochschu ...
and Walter Reppe develop metal-catalyzed
hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
and acetylene chemistry * 1951 Walter Hieber was awarded the
Alfred Stock Alfred Stock (July 16, 1876 – August 12, 1946) was a German inorganic chemist. He did pioneering research on the hydrides of boron and silicon, coordination chemistry, mercury, and mercury poisoning. The German Chemical Society's Alfred-Stoc ...
prize for his work with
metal carbonyl A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. These properties are all associated with having electrons available at the Fermi level, as against n ...
chemistry. * 1951
Ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
is discovered * 1956 Dorothy Crawfoot Hodgkin determines the structure of vitamin B12, the first biomolecule found to contain a metal-carbon bond, see bioorganometallic chemistry * 1963
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
for Karl Ziegler and Giulio Natta on
Ziegler–Natta catalyst A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes ( alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility ...
* 1973
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
Geoffrey Wilkinson Sir Geoffrey Wilkinson FRS (14 July 1921 – 26 September 1996) was a Nobel laureate English chemist who pioneered inorganic chemistry and homogeneous transition metal catalysis. Education and early life Wilkinson was born at Springside, Todm ...
and Ernst Otto Fischer on
sandwich compound In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by hapticity, haptic, covalent bonds to two arene compound, arene (ring) ligands. The arenes have the formula , substituted derivatives (for example ...
s * 1981
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
Roald Hoffmann Roald Hoffmann (born Roald Safran; July 18, 1937) is a Polish-American theoretical chemist who won the 1981 Nobel Prize in Chemistry. He has also published plays and poetry. He is the Frank H. T. Rhodes Professor of Humane Letters Emeritus at C ...
and Kenichi Fukui for creation of the Woodward-Hoffman Rules * 2001
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
W. S. Knowles William Standish Knowles (June 1, 1917 – June 13, 2012) was an American chemist. He was born in Taunton, Massachusetts. Knowles was one of the recipients of the 2001 Nobel Prize in Chemistry. He split half the prize with Ryōji Noyori for the ...
, R. Noyori and Karl Barry Sharpless for asymmetric hydrogenation * 2005
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
Yves Chauvin, Robert Grubbs, and
Richard Schrock Richard Royce Schrock (born January 4, 1945) is an American chemist and Nobel laureate recognized for his contributions to the olefin metathesis reaction used in organic chemistry. Education Born in Berne, Indiana, Schrock went to Mission Ba ...
on metal-catalyzed alkene metathesis * 2010
Nobel prize The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
Richard F. Heck,
Ei-ichi Negishi was a Japanese chemist who was best known for his discovery of the Negishi coupling. He spent most of his career at Purdue University in the United States, where he was the Herbert C. Brown Distinguished Professor and the director of the Negi ...
,
Akira Suzuki is a Japanese chemist and Nobel Prize Laureate (2010), 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(0) complex, in 1979. Early life a ...
for palladium catalyzed cross coupling reactions


Scope

Subspecialty areas of organometallic chemistry include: *
Period 2 element A period 2 element is one of the chemical elements in the second row (or Periodic table period, period) of the periodic table, periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) ...
s: organolithium chemistry, organoberyllium chemistry, organoborane chemistry *
Period 3 element A period 3 element is one of the chemical elements in the third row (or period) of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of the el ...
s: organosodium chemistry, organomagnesium chemistry,
organoaluminium chemistry Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monome ...
, organosilicon chemistry *
Period 4 element A period 4 element is one of the chemical elements in the fourth row (or Period (periodic table), period) of the periodic table, periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) tr ...
s: organocalcium chemistry, organoscandium chemistry, organotitanium chemistry, organovanadium chemistry, organochromium chemistry, organomanganese chemistry, organoiron chemistry, organocobalt chemistry, organonickel chemistry, organocopper chemistry, organozinc chemistry, organogallium chemistry, organogermanium chemistry,
organoarsenic chemistry Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungic ...
, organoselenium chemistry *
Period 5 element A period 5 element is one of the chemical elements in the fifth row (or period) of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behaviour of the el ...
s: organoyttrium chemistry, organozirconium chemistry, organoniobium chemistry, organomolybdenum chemistry, organotechnetium chemistry,
organoruthenium chemistry Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy ...
, organorhodium chemistry, organopalladium chemistry, organosilver chemistry, organocadmium chemistry, organoindium chemistry,
organotin chemistry Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
, organoantimony chemistry, organotellurium chemistry *
Period 6 element A period 6 element is one of the chemical elements in the sixth row (or period) of the periodic table of the chemical elements, including the lanthanides. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the ...
s: organolanthanide chemistry, organocerium chemistry, organotantalum chemistry, organotungsten chemistry, organorhenium chemistry, organoosmium chemistry, organoiridium chemistry, organoplatinum chemistry, organogold chemistry, organomercury chemistry, organothallium chemistry,
organolead chemistry Organolead chemistry is the scientific study of the synthesis and properties of organolead compounds, which are organometallic compounds containing a chemical bond between carbon and lead. The first organolead compound was hexaethyldilead (Pb2(C2 ...
, organobismuth chemistry, organopolonium chemistry *
Period 7 element A period 7 element is one of the chemical elements in the seventh row (or period) of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of the e ...
s: organoactinide chemistry, organothorium chemistry, organouranium chemistry, organoneptunium chemistry


Industrial applications

Organometallic compounds find wide use in commercial reactions, both as homogenous catalysts and as stoichiometric reagents. For instance, organolithium, organomagnesium, and
organoaluminium compound Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer ...
s, examples of which are highly basic and highly reducing, are useful stoichiometrically but also catalyze many polymerization reactions. Almost all processes involving carbon monoxide rely on catalysts, notable examples being described as
carbonylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...
s. The production of acetic acid from methanol and carbon monoxide is catalyzed via metal carbonyl complexes in the Monsanto process and
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. The process is based on an ...
. Most synthetic aldehydes are produced via
hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by
hydrogenation 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 hydroformylation-derived aldehydes. Similarly, the
Wacker process The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name) is an industrial chemical reaction: the aerobic oxidation of ethylene to acetaldehyde in the presence of catalysis, catalytic, aqueous palladium( ...
is used in the oxidation of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...
to
acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...
. Almost all industrial processes involving
alkene 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 Alpha-olefin, α-olefins. The Internationa ...
-derived polymers rely on organometallic catalysts. The world's polyethylene and polypropylene are produced via both heterogeneously via Ziegler–Natta catalysis and homogeneously, e.g., via constrained geometry catalysts. Most processes involving hydrogen rely on metal-based catalysts. Whereas bulk
hydrogenation 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 ...
s (e.g., margarine production) rely on heterogeneous catalysts, for the production of fine chemicals such hydrogenations rely on soluble (homogenous) organometallic complexes or involve organometallic intermediates. Organometallic complexes allow these hydrogenations to be effected asymmetrically. Many
semiconductors A semiconductor is a material with electrical conductivity between that of a conductor and an insulator. Its conductivity can be modified by adding impurities (" doping") to its crystal structure. When two regions with different doping levels ...
are produced from
trimethylgallium Trimethylgallium, often abbreviated to TMG or TMGa, is the organogallium compound with the formula Ga(CH3)3. It is a colorless, pyrophoric liquid. Unlike trimethylaluminium, TMG adopts a monomeric structure. When examined in detail, the monome ...
,
trimethylindium Trimethylindium, often abbreviated to TMI or TMIn, is the organoindium compound with the formula In(CH3)3. It is a colorless, pyrophoric solid. Unlike trimethylaluminium, but akin to trimethylgallium, TMI is monomeric. Preparation TMI is prepare ...
,
trimethylaluminium Trimethylaluminium or TMA is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula (abbreviated as , where Me stands for methyl), as it exists as a dimer. This colorless liquid is pyrophoric. It is an ...
, and trimethylantimony. These volatile compounds are decomposed along with
ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
,
arsine Arsine (IUPAC name: arsane) is an inorganic compound with the formula As H3. This flammable, pyrophoric, and highly toxic pnictogen hydride gas is one of the simplest compounds of arsenic. Despite its lethality, it finds some applications in th ...
,
phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...
and related hydrides on a heated substrate via metalorganic vapor phase epitaxy (MOVPE) process in the production of
light-emitting diode A light-emitting diode (LED) is a semiconductor device that emits light when current flows through it. Electrons in the semiconductor recombine with electron holes, releasing energy in the form of photons. The color of the light (corre ...
s (LEDs).


Organometallic reactions

Organometallic compounds undergo several important reactions: *
associative In mathematics, the associative property is a property of some binary operations that rearranging the parentheses in an expression will not change the result. In propositional logic, associativity is a valid rule of replacement for express ...
and
dissociative substitution In chemistry, dissociative substitution describes a reaction pathway by which compounds interchange ligands. The term is typically applied to coordination and organometallic complexes, but resembles the SN1 mechanism in organic chemistry. Thi ...
* oxidative addition and reductive elimination * transmetalation * migratory insertion * β-hydride elimination *
electron transfer Electron transfer (ET) occurs when an electron relocates from an atom, ion, or molecule, to another such chemical entity. ET describes the mechanism by which electrons are transferred in redox reactions. Electrochemical processes are ET reactio ...
* carbon-hydrogen bond activation * carbometalation * hydrometalation * cyclometalation * nucleophilic abstraction The synthesis of many organic molecules are facilitated by organometallic complexes. Sigma-bond metathesis is a synthetic method for forming new carbon-carbon
sigma bond In chemistry, sigma bonds (σ bonds) or sigma overlap are the strongest type of covalent chemical bond. They are formed by head-on overlapping between atomic orbitals along the internuclear axis. Sigma bonding is most simply defined for diat ...
s. Sigma-bond metathesis is typically used with early transition-metal complexes that are in their highest oxidation state. Using transition-metals that are in their highest oxidation state prevents other reactions from occurring, such as oxidative addition. In addition to sigma-bond metathesis, olefin metathesis is used to synthesize various carbon-carbon
pi bond In chemistry, pi bonds (π bonds) are covalent chemical bonds, in each of which two lobes of an orbital on one atom overlap with two lobes of an orbital on another atom, and in which this overlap occurs laterally. Each of these atomic orbital ...
s. Neither sigma-bond metathesis or olefin metathesis change the oxidation state of the metal. Many other methods are used to form new carbon-carbon bonds, including beta-hydride elimination and
insertion reaction An insertion reaction is a chemical reaction where one chemical entity (a molecule or molecular fragment) interposes itself into an existing Chemical bond, bond of typically a second chemical entity ''e.g.'': : + \longrightarrow The term only ...
s.


Catalysis

Organometallic complexes are commonly used in catalysis. Major industrial processes include
hydrogenation 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 ...
, hydrosilylation, hydrocyanation, olefin metathesis, alkene polymerization, alkene oligomerization,
hydrocarboxylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...
, methanol carbonylation, and
hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
. Organometallic intermediates are also invoked in many
heterogeneous catalysis Heterogeneous catalysis is catalysis where the Phase (matter), phase of catalysts differs from that of the reagents or product (chemistry), products. The process contrasts with homogeneous catalysis where the reagents, products and catalyst exis ...
processes, analogous to those listed above. Additionally, organometallic intermediates are assumed for
Fischer–Tropsch process The Fischer–Tropsch process (FT) is a collection of chemical reactions that converts a mixture of carbon monoxide and hydrogen, known as syngas, into liquid hydrocarbons. These reactions occur in the presence of metal catalysts, typically at te ...
. Organometallic complexes are commonly used in small-scale fine chemical synthesis as well, especially in
cross-coupling reaction In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important re ...
s that form carbon-carbon bonds, e.g. Suzuki-Miyaura coupling, Buchwald-Hartwig amination for producing aryl amines from aryl halides, and
Sonogashira coupling The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...
, etc.


Environmental concerns

Natural and contaminant organometallic compounds are found in the environment. Some that are remnants of human use, such as organolead and organomercury compounds, are toxicity hazards.
Tetraethyllead Tetraethyllead (commonly styled tetraethyl lead), abbreviated TEL, is an organolead compound with the formula lead, Pb(ethyl group, C2H5)4. It was widely used as a fuel additive for much of the 20th century, first being mixed with gasoline begi ...
was prepared for use as a
gasoline Gasoline ( North American English) or petrol ( Commonwealth English) is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When for ...
additive but has fallen into disuse because of lead's toxicity. Its replacements are other organometallic compounds, such as
ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
and methylcyclopentadienyl manganese tricarbonyl (MMT). The
organoarsenic compound Organoarsenic chemistry is the chemistry of Chemical compound, compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herb ...
roxarsone is a controversial animal feed additive. In 2006, approximately one million kilograms of it were produced in the U.S alone.
Organotin compounds Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
were once widely used in
anti-fouling paint Anti-fouling paint is a specialized category of coatings applied as the outer (outboard) layer to the hull of a ship or boat, to slow the growth of and facilitate detachment of subaquatic organisms that attach to the hull and can affect a ve ...
s but have since been banned due to environmental concerns.


See also

* Bioorganometallic chemistry * Metal carbon dioxide complex


References


Sources

* * * * * * * * *


External links


MIT OpenCourseWare: Organometallic Chemistry

Rob Toreki's Organometallic HyperTextbook

web listing of US chemists who specialize in organometallic chemistry
. {{DEFAULTSORT:Organometallic Chemistry