Baudisch Reaction
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Baudisch Reaction
In organic chemistry, the Baudisch reaction is a process for the synthesis of nitrosophenols using metal ions. Although the products are of limited value, the reaction is of historical interest as an example of metal-promoted functionalization of aromatic substrates. History and Mechanism As described originally by Oskar Baudisch in 1939 and further developed by his colleague Cronheim in 1947, benzene, hydroxylamine, and hydrogen peroxide are combined. Baudisch proposed that the reaction proceeds first via the formation of nitroxyl (HN=O), by the oxidation of hydroxylamine hydrochloride with hydrogen peroxide, possibly catalysed by the cupric ions. : This can also be achieved by the reduction of nitrous acid with cuprous ions or by the action of cuprous ions and hydrogen peroxide on Piloty's acid. The nitroxyl (HN=O) then attacks the aromatic ring, giving a nitroso-cyclohexadiene which is rapidly hydroxylated before being oxidised by the peroxide to give the o-nitrosophenol as ...
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Oskar Baudisch
Oskar Baudisch (3 June 1881 – 29 March 1950) was an Austrian American biochemist and radiographer. He is mainly known for a chemical reaction that bears his name, the Baudisch reaction. Early life and education Baudisch was born to Joseph and Julie Baudisch in Maffersdorf, Austria, which is today Vratislavice nad Nisou, now part of the Czech Republic. He received his first education in chemistry at the Staatsgewerbeschule in Reichenberg. Since this kind of school was not sufficient to be allowed to start a Ph. D. thesis in Austria, he went abroad. Baudisch studied chemistry in Zurich, where he obtained his Ph.D. in 1904. Career In Europe After a year of military service in the Austro-Hungarian Army, he worked for his former chemistry teacher, Ferdinand Breinl, in Reichenberg. There he published a paper on the oxidation of proteins by hydrogen peroxide. He then joined the group of Eugen Bamberger at the University of Zurich as a private assistant. In 1907 he joined t ...
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Nitrophenol
Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself. Mono-nitrophenols with the formula HOC6H4NO2. Three isomeric nitrophenols exist: * ''o''-Nitrophenol (2-nitrophenol; OH and NO2 groups are neighboring; CAS number: 88-75-5), a yellow crystalline solid (m.p. 46 °C). * ''m''-Nitrophenol (3-nitrophenol, CAS number: 554-84-7), a yellow solid (m.p. 97 °C) and precursor to the drug mesalazine (5-aminosalicylic acid). * ''p''-Nitrophenol (4-nitrophenol, CAS number: 100-02-7), yellow crystals (m.p. 114 °C). It is a precursor to the rice herbicide fluorodifen, the pesticide parathion, and the human analgesic paracetamol (also known as acetaminophen). The mononitrated phenols are often hydrogenated to the corresponding aminophenols that are also useful industrially. Di- and trinitrophenols * 2,4-Dinitrophenol (m.p. 83 °C) is a moderately strong acid (pKa = 4.89). ...
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Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ...
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Oximes
In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides () with general structure . Oximes are usually generated by the reaction of hydroxylamine with aldehydes () or ketones (). The term ''oxime'' dates back to the 19th century, a combination of the words ''oxygen'' and ''imine''. Structure and properties If the two side-chains on the central carbon are different from each other—either an aldoxime, or a ketoxime with two different "R" groups—the oxime can often have two different geometric stereoisomeric forms according to the ''E''/''Z'' configuration. An older terminology of ''syn'' and ''anti'' was used to identify especially aldoximes according to whether the R group was closer or further from the hy ...
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Hydroxamic Acid
A hydroxamic acid is a class of organic compounds bearing the functional group RC(O)N(OH)R', with R and R' as organic residues and CO as a carbonyl group. They are amides (RC(O)NHR') wherein the NH center has an OH substitution. They are often used as metal chelators. Synthesis and reactions Hydroxamic acids are usually prepared from either esters or acid chlorides by a reaction with hydroxylamine salts. For the synthesis of benzohydroxamic acid, the overall equation is: :C6H5CO2Me + NH2OH → C6H5C(O)NHOH + MeOH Hydroxamic acids can also be synthesized from aldehydes and ''N''-sulfonylhydroxylamine via the Angeli-Rimini reaction. A well-known reaction of hydroxamic acid esters is the Lossen rearrangement. Coordination chemistry and biochemistry File:Ferrichrome.svg, Ferrichrome File:Deferoxamine-2D-skeletal.png , Deferoxamine File:Rhodotorulic acid.svg, Rhodotorulic acid File:Fe(hydroxamate)3.svg, Fe(III) complex of triacetylfusarinine Many hydroxamates have been ...
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Aldehyde
In organic chemistry, an aldehyde () 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 common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and 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 C=O 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 are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors. Al ...
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Substituted Benzene Reaction
A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to predict the product outcome in a reaction. It also is helpful for optimizing a reaction with regard to variables such as temperature and choice of solvent. A good example of a substitution reaction is halogenation. When chlorine gas (Cl2) is irradiated, some of the molecules are split into two chlorine radicals (Cl•), whose free electrons are strongly nu ...
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Baudisch Reaction With Substituents
Baudisch is a surname. Notable people with the surname include: * Gudrun Baudisch-Wittke (1907–1982), Austrian woman ceramist, sculptor, and painter * Oskar Baudisch Oskar Baudisch (3 June 1881 – 29 March 1950) was an Austrian American biochemist and radiographer. He is mainly known for a chemical reaction that bears his name, the Baudisch reaction. Early life and education Baudisch was born to Joseph ... (1881–1950), Austrian American biochemist and radiographer * Patrick Baudisch, German computer scientist {{surname German-language surnames ...
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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. They are the elements that can use d orbitals as valence orbitals to form chemical bonds. The lanthanide and actinide elements (the f-block) are called inner transition metals and are sometimes considered to be transition metals as well. Since they are metals, they are lustrous and have good electrical and thermal conductivity. Most (with the exception of group 11 and group 12) are hard and strong, and have high melting and boiling temperatures. They form compounds in any of two or more different oxidation states and bind to a variety of ligands to form coordination complexes that are often coloured. They form many useful alloys and are often employed as catalysts in elemental form or in compounds such as coordination complexes and oxides. Most are strongly param ...
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, and alkylation and acylation Friedel–Crafts reaction. Illustrative reactions The most widely practised example of this reaction is the ethylation of benzene. :: Approximately 24,700,000 tons were produced in 1999. (After dehydrogenation and polymerization, the commodity plastic polystyrene is produced.) In this process, acids are used as catalyst to generate the incipient carbocation. Many other electrophilic reactions of benzene are conducted, although on a much smaller scale; they are valuable routes to key intermediates. The nitration of benzene is achieved via the action of the nitronium ion as the electrophile. The sulfonation with fuming sulfuric acid gives benzenesulfonic ac ...
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Phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Properties Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water at phenol ...
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