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Transition Metal Carbyne Complex
Transition metal carbyne complexes are organometallic compounds with a triple bond between carbon and the transition metal. This triple bond consists of a σ-bond and two π-bonds. The HOMO of the carbyne ligand interacts with the LUMO of the metal to create the σ-bond. The two π-bonds are formed when the two HOMO orbitals of the metal back-donate to the LUMO of the carbyne. They are also called metal alkylidynes—the carbon is a carbyne ligand. Such compounds are useful in organic synthesis of alkynes and nitriles. They have been the focus on much fundamental research. Synthesis Transition metal carbyne complexes are most common for the early transition metals, especially niobium, tantalum, molybdenum, tungsten, and rhenium. They can also have low-valence metals as well as high-valence metals. The first Fischer carbyne complex was reported in 1973. Two years later in 1975, the first "Schrock carbyne" was reported. Many high-valent carbyne complexes have since been prepared, ...
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Organometallic Compound
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, 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 "metalorganics, metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complex ...
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Haloform
In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane () are replaced by halogen atoms. Many trihalomethanes find uses in industry as solvents or refrigerants. THMs are also environmental pollutants, and many are considered carcinogenic. Trihalomethanes with all the same halogen atoms are called haloforms. Table of common trihalomethanes Industrial uses Only chloroform has significant applications of the haloforms. In the predominant application, chloroform is required for the production of tetrafluoroethylene, precursor to teflon. Chloroform is fluorinated by reaction with hydrogen fluoride to produce chlorodifluoromethane (R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with difluorocarbene as an intermediate. :CHCl3 + 2 HF -> CHClF2 + 2 HCl :2 CHClF2 -> C2F4 + 2 HCl Refrigerants and solvents Trifluoromethane and chlorodifluoromethane are both used as refrigerants. Trihalomethanes relea ...
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Cobalt Carbonyl
Dicobalt octacarbonyl is an organocobalt compound with composition . This metal carbonyl is used as a reagent and catalyst in organometallic chemistry and organic synthesis, and is central to much known organocobalt chemistry. It is the parent member of a family of hydroformylation catalysts. Each molecule consists of two cobalt atoms bound to eight carbon monoxide ligands, although multiple structural isomers are known. Some of the carbonyl ligands are labile. Synthesis, structure, properties Dicobalt octacarbonyl an orange-colored, pyrophoric solid. It is synthesised by the high pressure carbonylation of cobalt(II) salts: : The preparation is often carried out in the presence of cyanide, converting the cobalt(II) salt into a hexacyanocobaltate(II) complex that reacts with carbon monoxide to yield . Acidification produces cobalt tetracarbonyl hydride, , which degrades near room temperature to dicobalt octacarbonyl and hydrogen. It can also be prepared by heating cobalt metal to ...
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Carbonyl Ligand
Metal carbonyls are coordination complexes of transition metals with carbon monoxide ligands. Metal carbonyls are useful in organic synthesis and as catalysts or catalyst precursors in homogeneous catalysis, such as hydroformylation and Reppe chemistry. In the Mond process, nickel tetracarbonyl is used to produce pure nickel. In organometallic chemistry, metal carbonyls serve as precursors for the preparation of other organometallic complexes. Metal carbonyls are toxic by skin contact, inhalation or ingestion, in part because of their ability to carbonylate hemoglobin to give carboxyhemoglobin, which prevents the binding of oxygen. Nomenclature and terminology The nomenclature of the metal carbonyls depends on the charge of the complex, the number and type of central atoms, and the number and type of ligands and their binding modes. They occur as neutral complexes, as positively-charged metal carbonyl cations or as negatively charged metal carbonylates. The carbon monoxide liga ...
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Bridging Ligand
In coordination chemistry, a bridging ligand is a ligand that connects two or more atoms, usually metal ions. The ligand may be atomic or polyatomic. Virtually all complex organic compounds can serve as bridging ligands, so the term is usually restricted to small ligands such as pseudohalides or to ligands that are specifically designed to link two metals. In naming a complex wherein a single atom bridges two metals, the bridging ligand is preceded by the Greek letter mu, μ, with a subscript number denoting the number of metals bound to the bridging ligand. μ2 is often denoted simply as μ. When describing coordination complexes care should be taken not to confuse μ with η ('eta'), which relates to hapticity. Ligands that are not bridging are called terminal ligands. List of bridging ligands Virtually all ligands are known to bridge, with the exception of amines and ammonia. Common bridging ligands include most of the common anions. Many simple organic ligands form str ...
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Dimer (chemistry)
A dimer () ('' di-'', "two" + ''-mer'', "parts") is an oligomer consisting of two monomers joined by bonds that can be either strong or weak, covalent or intermolecular. Dimers also have significant implications in polymer chemistry, inorganic chemistry, and biochemistry. The term ''homodimer'' is used when the two molecules are identical (e.g. A–A) and ''heterodimer'' when they are not (e.g. A–B). The reverse of dimerization is often called dissociation. When two oppositely charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after Niels Bjerrum. Noncovalent dimers Anhydrous carboxylic acids form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example, acetic acid forms a dimer in the gas phase, where the monomer units are held together by hydrogen bonds. Under special conditions, most OH-containing molecules form dimers, e.g. the water dimer. Excimers and exciplexes are excited structures with a short lifetime. ...
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Vinylidene
Methylidenecarbene (systematically named λ2-ethene and dihydrido-1κ2''H''-dicarbon(''C''—''C'')) is an organic compound with the chemical formula (also written [] or ). It is a metastability, metastable proton tautomer of acetylene, which only persists as an adduct. It is a colourless gas that phosphoresces in the far-infrared range. It is the simplest unsaturated carbene. Nomenclature The systematic names ''λ2-ethene'', and ''dihydrido-1κ2H-dicarbon(C—C)'', valid IUPAC names, are constructed according to the substitutive and additive nomenclatures, respectively. In appropriate contexts, methylidenecarbene can be viewed as ethene with two hydrogen atoms removed, or as ethane with four hydrogens removed; and as such, ''ethen-1-ylidene'' (or ''vinylidene'') or ''ethane-1-diylidene'', respectively, may be used as a context-specific systematic names, according to substitutive nomenclature. By default, these names pay no regard to the radicality of the methylidenecarbene m ...
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Electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL. Organic chemistry Addition of halogens These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reactions i ...
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Vinyl Group
In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound containing that group, namely where R is any other group of atoms. An industrially important example is vinyl chloride, precursor to PVC, a plastic commonly known as ''vinyl''. Vinyl is one of the alkenyl functional groups. On a carbon skeleton, sp2-hybridized carbons or positions are often called vinylic. Allyls, acrylates and styrenics contain vinyl groups. (A styrenic crosslinker with two vinyl groups is called '' divinyl benzene''.) Vinyl polymers Vinyl groups can polymerize with the aid of a radical initiator or a catalyst, forming vinyl polymers. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers. Reactivity Vinyl derivatives are alkenes. If activated ...
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Isonitrile
An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds. Properties Structure and bonding The C-N distance in isocyanides is 115.8 pm in methyl isocyanide. The C-N-C angles are near 180°. Akin to carbon monoxide, isocyanides are described by two resonance structures, one with a triple bond between the nitrogen and the carbon and one with a double bond between. The π lone pair of the nitrogen stabilizes the structure and is responsible of the linearity of isocyanides, although the reactivity of isocyanides reflects some carbene character, at least in a formal sense. Thus, both resonance structures are useful representations. They are sus ...
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