Piloty's Acid
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Piloty's Acid
Piloty's acid is an organic compound with the formula C6H5SO2N(H)OH. A white solid, it is the benzenesulfonyl derivative of hydroxylamine. It is one of the main reagents used to generate nitroxyl (HNO), a highly reactive species that is implicated in a some chemical and biochemical reactions.{{cite journal, title=Synthesis, chemistry, and Applications of Nitroxyl Ion Releasers Sodium Trioxodinitrate or Angeli's Salt and Piloty's Acid, author1=Hughes, Martin N., author2=Cammack, Richard, journal=Methods in Enzymology (Nitric Oxide, Part C: Biological and Antioxidant Activities), year=1999, volume=301, pages=279–287, doi=10.1016/S0076-6879(99)01092-7 , pmid=9919577 See also * Angeli's salt Angeli's salt, sodium trioxodinitrate, is the inorganic compound with the formula Na2 2O3 It contains nitrogen in an unusual reduced state. It is a colorless, water-soluble solid, a salt. In research, this salt is used as a source of the metas ... References Hydroxylamines Sulfonamides ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Benzenesulfonic Acid
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C6 H6 O3 S. It is the simplest aromatic sulfonic acid. It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. It is often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic. Preparation Benzenesulfonic acid is prepared from the sulfonation of benzene using concentrated sulfuric acid: : This conversion illustrates aromatic sulfonation, which has been called "one of the most important reactions in industrial organic chemistry". Reactions Benzenesulfonic acid exhibits the reactions typical of other aromatic sulfonic acids, forming sulfonamides, sulfonyl chloride, and esters. The sulfonation is reversed above 220 °C. Dehydration with phosphorus pentoxide gives benzenesulfonic acid anhydride ((C6H5SO2)2O). Conver ...
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Hydroxylamine
Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–432. 1997. Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. It is also an intermediate in biological nitrification. The oxidation of to hydroxylamine is a step in biological nitrification. History Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate. It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944). The coordination complex , known as Crismer's salt, releases hydroxylamine upon heating. Production Hydroxylamine or its salts can be ...
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Reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, ''catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reagent ...
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Nitroxyl
Nitroxyl (common name) or azanone (IUPAC name) is the chemical compound HNO. It is well known in the gas phase. Nitroxyl can be formed as a short-lived intermediate in the solution phase. The conjugate base, NO−, nitroxide anion, is the redox reaction, reduced form of nitric oxide (NO) and is isoelectronic with dioxygen. The bond dissociation energy of H−NO is , which is unusually weak for a bond to the hydrogen atom. Generation Nitroxyl is produced from the reagents Angeli's salt (Na2N2O3) and Piloty's acid (PhSO2NHOH). Other notable studies on the production of HNO exploit cycloadducts of acyl nitroso species, which are known to decompose via hydrolysis to HNO and acyl acid. Upon photodissociation, photolysis these compounds release the acyl nitroso species which then further decompose. HNO is generated via organic oxidation of oxime, cyclohexanone oxime with lead tetraacetate to form 1-nitrosocyclohexyl acetate: : This compound can be hydrolyzed under base (chemistry), bas ...
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Angeli's Salt
Angeli's salt, sodium trioxodinitrate, is the inorganic compound with the formula Na2[N2O3]. It contains nitrogen in an unusual reduced state. It is a colorless, water-soluble solid, a salt. In research, this salt is used as a source of the metastable nitroxyl (HNO), which is a signalling molecule in nature. It is also known by the name sodium trioxodinitrate(II) monohydrate. Preparation and properties As first reported by Angelo Angeli in 1896, the salt is prepared by combining hydroxylamine and an organic nitrate, as a source of nitronium (): :NH2OH + RONO2 + 2 NaOR′ → ROH + 2 R′OH + Na2N2O3 The structure of the hydrate has been confirmed by X-ray crystallography. The anion is planar. Starting from the ONN end, the bond distances are 1.35 Å (N−O), 1.26 Å (N−N), 1.31 Å (N−O), and 1.32 Å (N−-O). The negative charge is on the oxygen atoms at opposite ends of the molecule. The angles are 112.9° (Osingle−N−N), 118.4° ...
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Hydroxylamines
Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–432. 1997. Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. It is also an intermediate in biological nitrification. The oxidation of to hydroxylamine is a step in biological nitrification. History Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate. It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944). The coordination complex , known as Crismer's salt, releases hydroxylamine upon heating. Production Hydroxylamine or its salts can be ...
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Sulfonamides
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this group is unreactive. Because of the rigidity of the functional group, sulfonamides are typically crystalline; for this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group. A sulfonamide (compound) is a chemical compound that contains this group. The general formula is or , where each R is some organic group; for example, "methanesulfonamide" (where R = methane, R' = R" = hydrogen) is . Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group () with an amine group. In medicine, the term "sulfonamide" is sometimes used as a synonym for sulfa drug, a derivative or var ...
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