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Imidazole-1-sulfonyl Azide
Imidazole-1-sulfonyl azide is an organic azide compound that can be used as an alternative to trifluoromethanesulfonyl azide. It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid. Preparation The hydrochloride salt of this compound is also available commercially, but can degrade to release explosive byproducts. : Reactions Like trifluoromethanesulfonyl azide, this compound generally converts primary amines or ammonium salts to azides when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts. This reaction is effectively the reverse of the Staudinger reaction. Similarly, it is able to transfer the diazo group (=N2) under basic conditions. Safety As with all organic azides, this compound is potentially explosive both in use and in preparation. The hydrochloride salt was initially reported to be insensitive to impact, vigorous grinding, and prolonged heating at 80 °C, although heating above 1 ...
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Azide
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant application of azides is as a propellant in air bags. Preparation Sodium azide is made industrially by the reaction of nitrous oxide, with sodium amide in liquid ammonia as solvent: : Many inorganic azides can be prepared directly or indirectly from sodium azide. For example, lead azide, used in detonators, may be prepared from the metathesis reaction between lead nitrate and sodium azide. An alternative route is direct reaction of the metal with silver azide dissolved in liquid ammonia. Some azides are produced by treating the carbonate salts with hydrazoic acid. Bonding Azide is isoelectronic with carbon dioxide , cyanate , nitrous oxide , nitronium ion and cyanogen fluoride NCF. Per valence bond theory, azide can be des ...
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Trifluoromethanesulfonyl Azide
Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis. Preparation Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. However, use of dichloromethane should be avoided because sodium azide is known to generate highly explosive azido-chloromethane and diazidomethane in situ by nucleophilic substitution on dichloromethane.Cavender, C. J.; Shiner, V. J., Jr. J. Org. Chem. (1972), 37, 3567. Moreover, the volatility of dichloromethane is a liability, as unsolvated triflyl azide is a detonation hazard. The reaction may also be carried out in toluene, acetonitrile, or pyridine. : (Tf = ) The trifluoromethanesulfonic anhydride starting material is rather expensive, and the product is explosive, and does not store well. As a result, imidazole-1-sulfonyl azide has been developed as an alternative ...
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Preparation Of Imidazole-1-sulfonyl Azide
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Organic Letters
''Organic Letters'' is a biweekly peer-reviewed scientific journal covering research in organic chemistry. It was established in 1999 and is published by the American Chemical Society. In 2014, the journal moved to a hybrid open access publishing model. The founding editor-in-chief was Amos Smith. Since 2019, Erick M. Carreira serves as the editor-in-chief. The journal is abstracted and indexed in: the Science Citation Index Expanded, Scopus, Academic Search Premier, BIOSIS Previews, Chemical Abstracts Service, EMBASE, and MEDLINE MEDLINE (Medical Literature Analysis and Retrieval System Online, or MEDLARS Online) is a bibliographic database of life sciences and biomedical information. It includes bibliographic information for articles from academic journals covering medic .... References External links * American Chemical Society academic journals Biweekly journals Organic chemistry journals Publications established in 1999 English-language journals {{chem-j ...
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Staudinger Reaction
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry: :R3P + R'N3 → R3P=NR' + N2 Staudinger reduction The Staudinger reduction is conducted in two steps. First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. The intermediate, e.g. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: :R3P=NR' + H2O → R3P=O + R'NH2 The overall conversion is a mild method of reducing an azide to an amine. Triphenylphosphine or tributylphosphine are most commonly used, yielding tributylphosphine oxide or triphenylphosphine oxide as a side product in addition to the desired amine. An example of a Staudinger reduction is the organic synthesis of the pinwheel compound 1,3,5-tris(aminomethyl)-2,4,6-triethylbenz ...
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Diazo
The diazo group is an organic moiety consisting of two linked nitrogen atoms ( azo) at the terminal position. Overall charge neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes and are described by the general structural formula R2C=N+=N–. The simplest example of a diazo compound is diazomethane, CH2N2. Diazo compounds (R2C=N2) should not be confused with azo compounds of the type R-N=N-R or with diazonium compounds of the type R-N2+. Structure The electronic structure of diazo compounds is characterized by π electron density delocalized over the α-carbon and two nitrogen atoms, along with an orthogonal π system with electron density delocalized over only the terminal nitrogen atoms. Because all octet rule-satisfying resonance forms of diazo compounds have formal charges, they are members of a class of compounds known as 1,3-dipoles. Some of the most stable diazo compounds are α-diazo-β-diketones ...
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Hygroscopy
Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance's molecules, adsorbing substances can become physically changed, e.g., changing in volume, boiling point, viscosity or some other physical characteristic or property of the substance. For example, a finely dispersed hygroscopic powder, such as a salt, may become clumpy over time due to collection of moisture from the surrounding environment. ''Deliquescent'' materials are sufficiently hygroscopic that they absorb so much water that they become liquid and form an aqueous solution. Etymology and pronunciation The word ''hygroscopy'' () uses combining forms of '' hygro-'' and '' -scopy''. Unlike any other ''-scopy'' word, it no longer refers to a viewing or imaging mode. It did begin that way, with the word ''hygroscope'' referring in the ...
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Hydrazoic Acid
Hydrazoic acid, also known as hydrogen azide or azoimide, This also contains a detailed description of the contemporaneous production process. is a compound with the chemical formula . It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes. Hydrazoic acid, like its fellow mineral acids, is soluble in water. Undiluted hydrazoic acid is dangerously explosive with a standard enthalpy of formation ΔfHo (l, 298K) = +264 kJ/mol. When dilute, the gas and aqueous solutions (<10%) can be safely prepared but should be used immediately; because of its low boiling point, hydrazoic acid is enriched upon evaporation and condensation such that dilute solutions incapable of explosion can form droplets in the headspace of the containe ...
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Sulfonyl Diazide
Sulfuryl diazide or sulfuryl azide is a chemical compound with the molecular formula . It was first described in the 1920s when its reactions with benzene and ''p''-xylene were studied by Theodor Curtius and Karl Friedrich Schmidt. The compound is reported as having "exceedingly explosive, unpredictable properties" and "in many cases very violent explosions occurred without any apparent reason". It was not until 2011 that sulfuryl diazide was isolated in a pure enough state to be fully characterized. It was characterized by infrared and Raman spectroscopy; its structure in the solid state was determined by x-ray crystallography. Its melting point is -15 °C. It was prepared by the reaction of sulfuryl chloride () with sodium azide () using acetonitrile as solvent: : Sulfuryl diazide has been used as a reagent to perform reactions that remove nitrogen from heterocyclic compounds: : See also * Trifluoromethanesulfonyl azide Trifluoromethanesulfonyl azide or triflyl azide ...
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Azido Compounds
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant application of azides is as a propellant in air bags. Preparation Sodium azide is made industrially by the reaction of nitrous oxide, with sodium amide in liquid ammonia as solvent: : Many inorganic azides can be prepared directly or indirectly from sodium azide. For example, lead azide, used in detonators, may be prepared from the metathesis reaction between lead nitrate and sodium azide. An alternative route is direct reaction of the metal with silver azide dissolved in liquid ammonia. Some azides are produced by treating the carbonate salts with hydrazoic acid. Bonding Azide is isoelectronic with carbon dioxide , cyanate , nitrous oxide , nitronium ion and cyanogen fluoride NCF. Per valence bond theory, azide can be desc ...
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Imidazoles
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam. When fused to a pyrimidine ring, it forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature. The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935). Structure and properties Imidazole is a planar 5-membered r ...
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