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Encyclopedia > Organometallic chemistry
n-butyllithium, an organometallic compound.
n-butyllithium, an organometallic compound.

Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal.[1] Often this definition is too strict however, since many compounds without such bonds are chemically similar. An appropriate alternative may be "compounds containing metal-element bonds of a largely covalent character". Organometallic chemistry combines aspects of inorganic chemistry and organic chemistry. Image File history File links Download high-resolution version (946x1073, 170 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Inorganic chemistry Organometallic chemistry N-Butyllithium User:Benjah-bmm27/Gallery User:Ben Mills/Gallery ... Image File history File links Download high-resolution version (946x1073, 170 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Inorganic chemistry Organometallic chemistry N-Butyllithium User:Benjah-bmm27/Gallery User:Ben Mills/Gallery ... An organolithium reagent is a carbon nucleophile similar to a Grignard reagent. ... A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... In chemistry, a chemical bond is the force which holds together atoms in molecules or crystals. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Hot metal work from a blacksmith In chemistry, a metal (Greek: Metallon) is an element that readily forms positive ions (cations) and has metallic bonds. ... Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well...

Contents

Organometallic compounds

Organometallic compounds are also known as organo-inorganics, metallo-organics and metalorganics. Organometallic compounds are distinguished by the prefix "organo-" e.g. organopalladium compounds. Examples of such organometallic compounds include all Gilman and Grignard reagents which contain lithium and copper, and magnesium respectively. Tetracarbonyl nickel, and ferrocene are examples of organometallic compounds containing transition metals. Metalorganics are also known as Organometallics or Metallo-Organics or Organo-Inorganics, and are used extensively in Metalorganic Vapor Phase Epitaxy (MOVPE) of compound semiconductors and Atomic Layer Deposition (ALD) in silicon-based semiconductors. ... A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, , where R is an organic radical. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... General Name, Symbol, Number lithium, Li, 3 Chemical series alkali metals Group, Period, Block 1, 2, s Appearance silvery white/grey Atomic mass 6. ... General Name, Symbol, Number copper, Cu, 29 Chemical series transition metals Group, Period, Block 11, 4, d Appearance metallic pinkish red Atomic mass 63. ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white Atomic mass 24. ... Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a colorless organometallic complex that is a versatile reagent, first described in 1890 by Ludwig Mond. ... Ferrocene is the chemical compound with the formula Fe(C5H5)2. ... In chemistry, the term transition metal (sometimes also called a transition element) has two possible meanings: It commonly refers to any element in the d-block of the periodic table, including zinc, cadmium and mercury. ...


In addition to the traditional metals and semimetals, elements such as boron, silicon, arsenic, and selenium are considered to form organometallic compounds. Examples include organomagnesium compounds such as iodo(methyl)magnesium MeMgI, diethylmagnesium (Et2Mg); organolithium compounds such as butyllithium (BuLi), organozinc compounds such as chloro(ethoxycarbonylmethyl)zinc (ClZnCH2C(=O)OEt); organocopper compounds such as lithium dimethylcuprate (Li+[CuMe2]); and organoborane compounds such as triethylborane (Et3B). General Name, Symbol, Number boron, B, 5 Chemical series metalloids Group, Period, Block 13, 2, p Appearance black/brown Atomic mass 10. ... General Name, Symbol, Number silicon, Si, 14 Chemical series metalloids Group, Period, Block 14, 3, p Appearance as coarse powder, dark gray with bluish tinge Atomic mass 28. ... General Name, Symbol, Number arsenic, As, 33 Chemical series metalloids Group, Period, Block 15, 4, p Appearance metallic gray Atomic mass 74. ... Se redirects here. ...


Many organometallic compounds exist in biological systems. For example, hemoglobin and myoglobin contain an iron center bonded to a porphyrin ring; magnesium is the center of a chlorin ring in chlorophyll. The specialized field of such inorganic compounds is known as bioinorganic chemistry. 3-dimensional structure of hemoglobin. ... An X-ray diffraction image for the protein myoglobin. ... General Name, Symbol, Number iron, Fe, 26 Chemical series transition metals Group, Period, Block 8, 4, d Appearance lustrous metallic with a grayish tinge Atomic mass 55. ... Core porphyrin structure 3D representation A porphyrin is a heterocyclic macrocycle made from 4 pyrrole subunits linked on opposite sides (α position) through 4 methine bridges (=CH-). The macrocycle, therefore, is more aromatic than the related corrins, chlorins (2,3-dihydroporphyrin) and bacteriochlorins (2,3,12,13-tetrahydroporphyrin). ... General Name, Symbol, Number magnesium, Mg, 12 Chemical series alkaline earth metals Group, Period, Block 2, 3, s Appearance silvery white Atomic mass 24. ... In organic chemistry, a chlorin is a large heterocyclic aromatic ring consisting, at the core, of 3 pyrroles and one reduced pyrrole coupled through 4 methine linkages. ... Chlorophyll gives leaves their green color Space-filling model of the chlorophyll molecule Chlorophyll is a green photosynthetic pigment found in most plants, algae, and cyanobacteria. ... An inorganic compound is a chemical compound that is not an organic compound. ... Bioinorganic Chemistry is a specialized field that spans the chemistry of metal-containing molecules. ...


Structure and properties

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.


Depending mostly on the nature of metallic ion and somewhat on the nature of the organic compound, the character of the bond may either be ionic or covalent. Organic compounds bonded to sodium or potassium are primarily ionic. Those bonded to lead, tin, mercury, etc. are considered to have covalent bonds, and those bonded to magnesium or lithium have bonds with intermediate properties. Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Covalent bonding is a description of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. ...


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 or dibenzenechromium, the pi orbitals of the organic moiety ligate the metal. An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... Ferrocene is the chemical compound with the formula Fe(C5H5)2. ... Electron atomic and molecular orbitals, showing a Pi-bond at the bottom right of the picture In chemistry, pi bonds (Ï€ bonds) are chemical bonds of the covalent type, where two lobes of one involved electron orbital overlap two lobes of the other involved electron orbital. ...


Applications

Organometallic compounds find practical use in stoichiometric and catalytically active compounds. Formerly, tetraethyl lead was added to gasoline as an antiknock agent. It is no longer used due to lead's toxicity, being replaced with other organometallic compounds such as ferrocene and methylcyclopentadienyl manganese tricarbonyl (MMT) are used. In chemistry, stoichiometry is the study of the combination of elements in chemical reactions. ... It has been suggested that this article or section be merged into Catalysis. ... Tetra-ethyl lead (also known as TEL, lead tetraethyl and tetraethyllead) is a toxic organometallic chemical compound, with formula (CH2CH3)4Pb, which was once used as a gasoline (petrol) additive. ... Gasoline or petrol is a petroleum-derived liquid mixture consisting mostly of hydrocarbons and enhanced with benzene or iso-octane to increase octane ratings, used as fuel in internal combustion engines. ... An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuels octane rating. ... Ferrocene is the chemical compound with the formula Fe(C5H5)2. ... Methyl Cyclopentadienyl Manganese Tricarbonyl (MMT) is a fuel additive that can increase fuel octane levels. ...


The Monsanto process utilizes a rhodium-carbonyl complex to manufacture acetic acid from methanol and carbon monoxide industrially. The Ziegler-Natta catalyst is a titanium-based organometallic compound used in the production of polyethylene and other polymers. A major route to Acetic acid is the rhodium-catalysed Monsanto process. ... Rh redirects here. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Methanol, also known as methyl alcohol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Carbon monoxide, with the chemical formula CO, is a colourless, odourless and tasteless gas. ... A Ziegler-Natta catalyst is a reagent used in the production of unbranched, stereoregular vinyl polymers. ... This article or section does not cite its references or sources. ...


In the production of fine chemicals and pharmaceuticals, Ryoji Noyori's chiral ruthenium-BINAP complex catalytically reduces beta-ketoesters to secondary alcohols. In drug manufacture, fine chemicals are pure, single chemical substances that are produced by chemical reactions. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... Ryoji Noyori (野依良治) (born September 3, 1938) won the Nobel Prize in Chemistry in 2001. ... General Name, Symbol, Number Ruthenium, Ru, 44 Chemical series transition metals Group, Period, Block 8, 5, d Appearance silvery white metallic Atomic mass 101. ... Figure 1 (S)- and (R)-BINAP In organic chemistry, BINAP, an acronym used for 2,2-bis(diphenylphosphino)-1,1-binaphthyl, is an important chiral ligand widely used in asymmetric synthesis. ...


Concepts

Electron counting is the cornerstone of organometallic chemistry. The 18-electron rule is helpful in predicting the stabilities of organometallic compounds. Organometallic compounds which have 18 electrons (filled s, p, and penultimate d orbitals) are relatively stable. While this suggests the compound is isolable, it may also result in the compound being inert. Electron counting is a formalism used for classifying compounds and for explaining or predicting electronic structure and bonding. ... The valence shells of a transition metal can accommodate 18 electrons: 2 in each of the five d orbitals, to give 10 in total; 2 in each of the 3 p orbitals, to give 6 in total; and 2 in the s orbital (see Electron counting). ...


The isolobal principle helps to understand chemical bonding and reactivity in organometallic compounds. NMR and infrared spectroscopy are common techniques used to determine structure and bonding in this field. In particular, variable-temperature NMR allows scientists to probe fluxional behaviors of compounds. The isolobal principle in organometallic chemistry devised by Roald Hoffman aims to improve the understanding of chemical bonding in molecules by identifying molecules that share a common frontier orbital type, approximate energy and occupancy just as isoelectronic molecules share the same number of valence electrons and structure . ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... IR spectrum of a thin film of liquid ethanol. ...


Organometallic compounds undergo several important reactions:

Oxidative addition and reductive elimination are two important classes of reactions in organometallic chemistry. ... Oxidative addition and reductive elimination are two important classes of reactions in organometallic chemistry. ... Transmetalation is a general chemical reaction type in organometallic chemistry describing the exchange of ligands between two metal centers. ... 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 yield the cis or trans isomer and with unsymmetrical alkynes the... Electron transfer (ET) is the process by which an electron moves from one atom or molecule to another atom or molecule. ... This is a organometallic reaction in which an alkyl group bonded to a metal centre is converted into a metal bonded hydride and an alkene. ...

History

Early developments in organometallic chemistty include Louis Claude Cadet’s synthesis of methyl arsenic compounds related to the cacodylic acid, William Christopher Zeise's platinum-ethylene complex, Edward Frankland’s discovery of dimethyl zinc, Ludwig Mond’s discovery of Ni(CO)4, and Victor Grignard’s organomagnesium compounds. The abundant and diverse products from coal and petroleum led to Ziegler-Natta, Fischer-Tropsch, hydroformylation catalysis which employ CO, H2, and alkenes as feedstocks and ligands. Cacodylic acid (also called dimethylarsinic acid) has the chemical formula (CH3)2AsO2H. Derivates of cacodylic acid, cacodylates, were frequently used as herbicides. ... William Christopher Zeise (October 15, 1789 – November 12, 1847) was a Danish organic chemist. ... ... Sir Edward Frankland (January 18, 1825 – August 9, 1899) was an English chemist. ... Dr Ludwig Mond (born March 7, 1839, Kassel; died December 11, 1909, London) was an important German-born British chemist and industrialist. ... Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a colorless organometallic complex that is a versatile reagent, first described in 1890 by Ludwig Mond. ... François Auguste Victor Grignard (born in Cherbourg, 6 May 1871, died in Lyon, 13 December 1935) was a Nobel Prize-winning French chemist. ... A Ziegler-Natta catalyst is a reagent used in the production of unbranched, stereoregular vinyl polymers. ... Fischer-Tropsch Process for Synthetic Diesel Fuel The Fischer-Tropsch process is a catalyzed chemical reaction in which carbon dioxide, carbon monoxide and methane are converted into liquid hydrocarbons of various forms. ... Hydroformylation is the transformation of an alkene to an aldehyde via the addition of both H2 and CO. The aldehyde has one more carbon atom than the precursor alkene. ...


Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to Ernst Fischer and Geoffrey Wilkinson for work on metallocenes. In 2005, Yves Chauvin, Robert H. Grubbs and Richard R. Schrock shared the Nobel Prize for metal-catalyzed olefin metathesis. Ernst Otto Fischer is a German chemist who won the Nobel Prize for pioneering work in the area of organometallic chemistry. ... Sir Geoffrey Wilkinson was an English chemist He was born 14 July 1921 in the village of Springside, near Todmorden in Yorkshire. ... In chemistry, and in particular, in organometallic chemistry, a metallocene is a compound consisting of an aromatic organic ligand bound to a metal. ... Yves Chauvin (born October 10, 1930) is a French chemist and Nobel Prize winner. ... Robert H. Grubbs (b. ... Richard Royce Schrock (born January 4, 1945) was one of the recipients of the 2005 Nobel Prize in Chemistry for his contribution to the metathesis method in organic chemistry. ... Olefin metathesis or transalkylidenation (in some literature, a disproportionation) is an organic reaction which involves redistribution of olefinic (alkene) bonds. ...


Organometallic chemistry timeline

This article or section does not cite its references or sources. ... Space-filling model of cacodyl Cacodyl, dicacodyl, tetramethyldiarsine, alkarsine or Cadets liquid (after the French chemist Louis Claude Cadet de Gassicourt) (CH3)2As—As(CH3)2 is a poisonous oily liquid with a garlicky odor. ... General Name, Symbol, Number arsenic, As, 33 Chemical series metalloids Group, Period, Block 15, 4, p Appearance metallic gray Atomic mass 74. ... ... General Name, Symbol, Number platinum, Pt, 78 Chemical series transition metals Group, Period, Block 10, 6, d Appearance grayish white Atomic mass 195. ... A synonym for the more widely accepted term, alkene. ... Charles Friedel (March 12, 1832 – April 20, 1899) was a French chemist and mineralogist. ... James Mason Crafts (March 8, 1839 – 20 June 1917) was an American chemist, most known for developing the Friedel-Crafts alkylation and acylation reactions with Charles Friedel in 1876. ... Dr Ludwig Mond (born March 7, 1839, Kassel; died December 11, 1909, London) was an important German-born British chemist and industrialist. ... Nickel carbonyl, or tetracarbonylnickel is the compound Ni(CO)4. ... The Grignard reaction is an organometallic chemical reaction involving alkyl- or aryl-magnesium halides, also called Grignard reagents, with electrophiles. ... Paul Sabatier (November 5, 1854 – August 14, 1941) was a French chemist, born at Carcassonne. ... Hydrogenation is a class of chemical reactions in which the net result is an addition of hydrogen. ... Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... The food industry is the complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population. ... Margarine in a tub Margarine (pronunciation: ), as a generic term, can indicate any of a wide range of butter-substitutes. ... Nobel Prize medal. ... François Auguste Victor Grignard (born in Cherbourg, 6 May 1871, died in Lyon, 13 December 1935) was a Nobel Prize-winning French chemist. ... Paul Sabatier (November 5, 1854 – August 14, 1941) was a French chemist, born at Carcassonne. ... Henry Gilman was born in Boston, Massachusetts, on May 19, 1893. ... A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, , where R is an organic radical. ... Nobel Prize medal. ... Karl Waldemar Ziegler (November 26, 1898 – August 12, 1973) was a German chemist who won the Nobel Prize in Chemistry in 1963, with Giulio Natta, for work on high polymers. ... Giulio Natta (February 26, 1903 – May 2, 1979) was an Italian chemist. ... A Ziegler-Natta catalyst is a reagent used in the production of unbranched, stereoregular vinyl polymers. ... Cyclobutadieneiron tricarbonyl or (C4H4)Fe(CO)3 is an organometallic complex of cyclobutadiene and an iron metal carbonyl. ... In organic chemistry, the Heck reaction or the Mizoroki-Heck reaction couples an unsaturated halide or triflate with an alkene in a basic solution. ... Nobel Prize medal. ... Sir Geoffrey Wilkinson was an English chemist He was born 14 July 1921 in the village of Springside, near Todmorden in Yorkshire. ... Ernst Otto Fischer is a German chemist who won the Nobel Prize for pioneering work in the area of organometallic chemistry. ... Space-filling model of ferrocene, the archetypal sandwich compound A sandwich compound in organometallic chemistry is any chemical compound containing a metal atom sandwiched between two arene units. ... Nobel Prize medal. ... Yves Chauvin (born October 10, 1930) is a French chemist and Nobel Prize winner. ... Robert Howard Grubbs (b. ... Richard Royce Schrock (born January 4, 1945) was the recipient of the 2005 Nobel Prize in Chemistry for his contribution to the metathesis method in organic chemistry. ... Olefin metathesis or transalkylidenation (in some literature, a disproportionation) is an organic reaction which involves redistribution of olefinic (alkene) bonds. ...

Organometallics

A period 2 element is one of the chemical elements in the second row (or period) of the periodic table of the elements. ... An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom. ... Organoborane or organoboron compounds are chemical compounds comprised of boron and carbon. ... A period 3 element is one of the chemical elements in the third row (or period) of the periodic table of the elements. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... Organosilicon compounds are chemical compounds containing carbon silicon bonds. ... A period 4 element is one of the chemical elements in the fourth row (or period) of the periodic table of the elements. ... Organocopper compounds in organometallic chemistry contain carbon to copper chemical bonds. ... Organozinc compounds in organic chemistry contain carbon to zinc chemical bonds. ... Organogermanium compounds are organometallic compounds containing a carbon to germanium or hydrogen to germanium chemical bond. ... A period 5 element is one of the chemical elements in the fifth row (or period) of the periodic table of the elements. ... Organopalladium chemistry is a branch of organometallic chemistry and deals with organic palladium compounds and their reactions. ... An organocadmium compound is a organometallic compound containing a carbon to cadmium chemical bond. ... Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. ... A period 6 element is one of the chemical elements in the sixth row (or period) of the periodic table of the elements, including the Lanthanides. ... Organomercury refers to the group of organometallic compounds containing mercury. ...

See also

Chelation (from Greek χηλή, chelè, meaning claw) is the process of reversible binding (complexation) of a ligand - the chelant, chelator, chelating agent, sequestering agent, or complexing agent - to a metal ion, forming a metal complex, the chelate. ... Bioorganometallic chemistry is the study of biologically active molecules that contain carbon directly bonded to metals or metalloids. ...

References

  1. ^ Robert H. Crabtree (2005). The Organometallic Chemistry of the Transition Metals. Wiley, 560. ISBN 978-0-471-66256-3. 

Robert H. Crabtree (born 1948 in London) is a British chemist. ...

External links

  • MIT OpenCourseWare: Organometallic Chemistry
  • Rob Toreki's Organometallic HyperTextbook

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organometallic chemistry - HighBeam Encyclopedia (519 words)
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