Alkoxides
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Alkoxides
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, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis.excerpt Transition metal alkoxides are widely used for coatings and as catalysts. Enolates are unsaturated alkoxides derived by deprotonation of a bond adjacent to a ketone or aldehyde. The nucleophilic center for simple alkoxides is located on the oxygen, whereas the nucleophilic site on enolates is delocalized onto both carbon and oxygen sites. Ynolates are also unsaturated alkoxides derived from acetylenic alcohols. Phenoxides are close relatives of the alkoxides, in which the alkyl group is replaced by a phenyl ...
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Sodium Methoxide
Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. Preparation and structure Sodium methoxide is prepared by treating methanol with sodium: : The reaction is so exothermic that ignition is possible. The resulting solution, which is colorless, is often used as a source of sodium methoxide, but the pure material can be isolated by evaporation followed by heating to remove residual methanol. As a solid, sodium methoxide is polymeric, with sheet-like arrays of centers, each bonded to four oxygen centers. The structure, and hence the basicity, of sodium methoxide in solution depends on the solvent. It is a significantly stronger base in DMSO where it is more fully ionized and free of hydrogen bonding. Applications Organic synthesis Sodium methoxide is a routinely used base in organic ch ...
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Catalyst
Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. The rate increase occurs because the catalyst allows the reaction to occur by an alternative mechanism which may be much faster than the noncatalyzed mechanism. However the noncatalyzed mechanism does remain possible, so that the total rate (catalyzed plus noncatalyzed) can only increase in the presence of the catalyst and never decrease. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usual ...
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Hydrogen
Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter. Under standard conditions, hydrogen is a gas of diatomic molecules with the chemical formula, formula , called dihydrogen, or sometimes hydrogen gas, molecular hydrogen, or simply hydrogen. Dihydrogen is colorless, odorless, non-toxic, and highly combustible. Stars, including the Sun, mainly consist of hydrogen in a plasma state, while on Earth, hydrogen is found as the gas (dihydrogen) and in molecular forms, such as in water and organic compounds. The most common isotope of hydrogen (H) consists of one proton, one electron, and no neutrons. Hydrogen gas was first produced artificially in the 17th century by the reaction of acids with metals. Henry Cavendish, in 1766–1781, identified hydrogen gas as a distinct substance and discovere ...
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Acid
An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acid–base theory, Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Acid–base reaction#Arrhenius theory, Arrhenius acids. Johannes Nicolaus Brønsted, Brønsted and Martin Lowry, Lowry generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted–Lowry or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H+. Aqueous Arrhenius acids have characteristic properties that provide a practical description of an acid. Acids form aqueous solutions with a sour taste, can turn blue litmus red, and ...
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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 s ...
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Phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. It is acutely toxic and is considered a health hazard. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds, and is a liquid when manufactured. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceuti ...
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Phenoxides
Phenolates (also called phenoxides) are anions, salts, and esters of phenols, containing the phenolate ion. They may be formed by reaction of phenols with strong base. Properties Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions. At pH = 10, phenol and phenolate are in approximately 1:1 proportions. The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines. Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control). Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control. Uses Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide: :C6H5ONa + CH3I → C6H5OCH3 + NaI :C6H5ONa + (CH3O)2SO2 → C6H5OCH3 + (CH3 ...
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Ynolate
In organic chemistry, alkynols (''hydroxyalkynes'') are organic compounds that contain both alkyne and alcohol functional groups. Thus, as structural features, they have a C≡C triple bond and a hydroxyl group. Some alkynols play a role as intermediates in the chemical industry. The shortened term ynol typically refers to alkynols with the hydroxyl group affixed to one of the two carbon atoms composing the triple bond (), the triple-bond analogues to enols. Ynols can tautomerize to ketenes. The deprotonated anions of ynols are known as ynolates, the triple-bond analogues to enolates. Synthesis Alkynols may be formed by the alkynylation of carbonyl compounds, usually in liquid ammonia. Ynolates Ynolates are chemical compounds with a negatively charged oxygen atom attached to an alkyne functionality. They were first synthesized in 1975 by Schöllkopf and Hoppe via the ''n''-butyllithium fragmentation of 3,4-diphenylisoxazole. Synthetically, they behave as ketene pr ...
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Aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Structure and bonding Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The bond length is about 120–122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are solubl ...
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Ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula . Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, ''e.g.'', testosterone, and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introdu ...
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