Organoruthenium Compounds
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Organoruthenium Compounds
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. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl. In its organometallic compounds, ruthenium is known to adopt oxidation states from -2 ( u(CO)4sup>2−) to +6 ( uN(Me)4sup>−). Most common are those in the 2+ oxidation state, as illustrated below. File:Grubbs Catalyst 1st Generation.svg, 1st generation Grubbs catalyst File:ShvoCat.png, Shvo catalyst File:RuCymCl2.png, (cymene)ruthenium dichloride dimer File:Trirutheniumdodecacarbonyl.svg, triruthenium dodecacarbonyl. File:Chloro(cyclopentadienyl)bis(triphenylph ...
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Chemistry
Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo during a Chemical reaction, reaction with other Chemical substance, substances. Chemistry also addresses the nature of chemical bonds in chemical compounds. In the scope of its subject, chemistry occupies an intermediate position between physics and biology. It is sometimes called the central science because it provides a foundation for understanding both Basic research, basic and Applied science, applied scientific disciplines at a fundamental level. For example, chemistry explains aspects of plant growth (botany), the formation of igneous rocks (geology), how atmospheric ozone is formed and how environmental pollutants are degraded (ecology), the properties ...
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Chlorine
Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Electronegativity#Pauling electronegativity, Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval Alchemy, alchemists, which commonly involved the heating of chloride Salt (chemistry), salts like ammonium chloride (sal ammoniac) and sodium chloride (common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and hydrochloric acid (in the form of ). However ...
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Organic Syntheses
''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and experiments reported in an article must be successfully repeated in the laboratory of a member of the editorial board as a check for reproducibility prior to publication. The journal is published by Organic Syntheses, Inc., a non-profit corporation. An annual print version is published by John Wiley & Sons on behalf of Organic Syntheses, Inc. History Prior to World War I, work on synthetic organic chemistry in the United States had been quite limited, and most of the reagents used in laboratories had to be imported from Europe. When export stoppages and trade embargoes cut off this source, Clarence Derick, a professor of chemistry at University of Illinois at Urbana-Champaign, began an effort to synthesize these needed chemicals in industr ...
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Asymmetric Ligand
In homogeneous catalysis, ''C''2-symmetric ligands refer to ligands that lack mirror symmetry but have ''C''2 symmetry (two-fold rotational symmetry). Such ligands are usually bidentate and are valuable in catalysis. The ''C''2 symmetry of ligands limits the number of possible reaction pathways and thereby increases enantioselectivity, relative to asymmetrical analogues. ''C''2-symmetric ligands are a subset of chiral ligands. Chiral ligands, including ''C''2-symmetric ligands, combine with metals or other groups to form chiral catalysts. These catalysts engage in enantioselective chemical synthesis, in which chirality in the catalyst yields chirality in the reaction product. Examples An early ''C''2-symmetric ligand, diphosphine catalytic ligand DIPAMP, was developed in 1968 by William S. Knowles and coworkers of Monsanto Company, who shared the 2001 Nobel Prize in Chemistry. This ligand was used in the industrial production of -DOPA. : Some classes of ''C''2-symmetric li ...
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BINAP
BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions. This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation ( atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle between the naphthyl groups is approximately 90°. The natural bite angle is 93°. Use as ligand in asymmetric catalysis BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium. As pioneered by Ryōji Noyori and his co-workers, rhodium complexes of BINAP are useful for the synthesis of (–)-menthol. Silver complexes are also important; BINAP- AgF can be used to enantioselect ...
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Tricyclohexylphosphine
Tricyclohexylphosphine is the tertiary phosphine with the formula P( C6H11)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy3, where Cy stands for cyclohexyl. It is characterized by both high basicity (p''K''a = 9.7) and a large ligand cone angle (170°).{{cite journal , last1 = Immirzi , first1 = A. , last2 = Musco , first2 = A. , title = A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes , doi = 10.1016/S0020-1693(00)95635-4 , year = 1977 , journal = Inorg. Chim. Acta , volume = 25 , pages = L41–42 Important complexes containing P(Cy)3 ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst Crabtree's catalyst is an organoiridium compound with the formula ,5-Cyclooctadiene, C8H12IrTricyclohexylphosphine, P(C6H11)3pyridine, C5H5NF6. It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Rober ...
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Metal Carbene
A transition metal carbene complex is an organometallic compound featuring a divalent organic ligand. The divalent organic ligand coordinated to the metal center is called a carbene. Carbene complexes for almost all transition metals have been reported. Many methods for synthesizing them and reactions utilizing them have been reported. The term carbene ligand is a formalism since many are not derived from carbenes and almost none exhibit the reactivity characteristic of carbenes. Described often as , they represent a class of organic ligands intermediate between alkyls and carbynes . They feature in some catalytic reactions, especially alkene metathesis, and are of value in the preparation of some fine chemicals. Classification Metal carbene complexes are often classified into two types. The Fischer carbenes named after Ernst Otto Fischer feature strong π-acceptors at the metal and being electrophilic at the carbene carbon atom. Schrock carbenes, named after Richard R. Schrock ...
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Transition Metal Hydride
Transition metal hydrides are chemical compounds containing a transition metal bonded to hydrogen. Most transition metals form hydride complexes and some are significant in various catalytic and synthetic reactions. The term "hydride" is used loosely: some of them are acidic (e.g., H2Fe(CO)4), whereas some others are hydridic, having H−-like character (e.g., ZnH2). Classes of metal hydrides Binary metal hydrides Many transition metals form compounds with hydrogen, called binary hydrides: binary, because these compounds contain only two elements, and hydride, because the hydrogenic ligand is assumed to have hydridic (H−-like) character. These compounds are invariably insoluble in all solvents, reflecting their polymeric structures. They often exhibit metal-like electrical conductivity. Many are nonstoichiometric compounds. Electropositive metals ( Ti, Zr, Hf, Zn) and some other metals form hydrides with the stoichiometry MH or sometimes MH2 (M = Ti, Zr, Hf, V, Zn). The b ...
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Metal Carbonyl
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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Diene
In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition. Classes Dienes can be divided into three classes, depending on the relative location of the double bonds: #Cumulated dienes have the double bonds sharing a common atom. The result is more specifically called an allene. #Conjugated dienes have conjugated double bonds separated by one single bond. Conjugated dienes are more stable than other dienes because of resonance. #Unconjugated dienes have the double bonds separated by two or more single bonds. They are usually less stable tha ...
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Arene Compound
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties are understood. The current definition of aromatic compounds does not have any relation with their smell. Heteroarenes are closely related, since at least one carbon atom of CH group is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Benzene ring model Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one named as such ...
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Cyclopentadienyl
Cyclopentadienyl can refer to *Cyclopentadienyl anion, or cyclopentadienide, **Cyclopentadienyl ligand *Cyclopentadienyl radical, • *Cyclopentadienyl cation, See also *Pentadienyl In organic chemistry, pentadienyl refers to the organic radical, anion, or cation with the formula , where ''z'' = 0, −1, +1, respectively. Organometallic chemistry In organometallic chemistry, the pentadienyl anion is a ligand, the acyclic ana ...
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