Cyanocyclopropane
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Cyanocyclopropane
Cyclopropyl cyanide is an organic compound consisting of a nitrile group as a substituent on a cyclopropane ring. It is the smallest cyclic compound containing a nitrile. Structure The structure of cyclopropyl cyanide has been determined by a variety of experiments, including microwave spectroscopy, rotational spectroscopy and photodissociation. In 1958, cyclopropyl cyanide was first studied for its rotational spectra, by Friend and Dailey. An additional experiment involving cyclopropyl cyanide was the determination of the molecular dipole moment through spectroscopy experiments, by Carvalho in 1967. Production Cyclopropyl cyanide is prepared by the reaction of 4- chlorobutyronitrile with a strong base, such as sodium amide in liquid ammonia. Reactions Hydrolysis gives cyclopropane carboxylic acid]. Cyclopropyl cyanide, when heated to 660-760K and under pressure of 2-89torr, becomes cis and trans crotonitrile and allyl cyanide molecules, with some presence of methacrylonitril ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). 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, and even ...
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Sodium Amide
Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. has been widely employed as a strong base in organic synthesis. Preparation and structure Sodium amide can be prepared by the reaction of sodium with ammonia gas, but it is usually prepared by the reaction in liquid ammonia using iron(III) nitrate as a catalyst. The reaction is fastest at the boiling point of the ammonia, c. −33 °C. An electride, , is formed as a reaction intermediate. : is a salt-like material and as su ...
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Spectroscopy
Spectroscopy is the field of study that measures and interprets electromagnetic spectra. In narrower contexts, spectroscopy is the precise study of color as generalized from visible light to all bands of the electromagnetic spectrum. Spectroscopy, primarily in the electromagnetic spectrum, is a fundamental exploratory tool in the fields of astronomy, chemistry, materials science, and physics, allowing the composition, physical structure and electronic structure of matter to be investigated at the atomic, molecular and macro scale, and over astronomical distances. Historically, spectroscopy originated as the study of the wavelength dependence of the absorption by gas phase matter of visible light dispersed by a prism. Current applications of spectroscopy include biomedical spectroscopy in the areas of tissue analysis and medical imaging. Matter waves and acoustic waves can also be considered forms of radiative energy, and recently gravitational waves have been associa ...
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Methacrylonitrile
Methacrylonitrile (or 2-Methylprop-2-enenitrile), MeAN in short, is a chemical compound that is an unsaturated aliphatic nitrile, widely used in the preparation of homopolymers, copolymers, elastomers, and plastics and as a chemical intermediate in the preparation of acids, amides, amines, esters, and other nitriles. MeAN is also used as a replacement for acrylonitrile in the manufacture of an acrylonitrile/butadiene/styrene-like polymer. It is a clear and colorless (to slightly yellow) liquid, that has a bitter almond smell. It is toxic by ingestion, inhalation, and skin absorption. Exposure and regulation Since MeAN is present in polymeric coating materials as found in many everyday use items, humans are exposed to it by skin absorption. Aside from this there is an occupational exposure, and low levels of MeAN are also present in the smoke of unfiltered cigarettes made from air-cured or flue-cured tobaccos. Due to the toxicity of MeAN, the U.S. Department of Health & Human Se ...
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Allyl Cyanide
Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is colorless and soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent in some polymers. Synthesis Allyl cyanide is obtained by the reaction of allyl acetate with hydrogen cyanide. A laboratory route to allyl cyanide involves treating allyl bromide with copper(I) cyanide. :CH2=CHCH2Br + CuCN → CH2=CHCH2CN + CuBr Other allyl halides may be used for this reaction including allyl iodide as done by A. Rinne and B. Tollens in 1871 where iodide is a better leaving group than its bromide equivalent and therefore increases the yield. Natural occurrences Allyl cyanide was discovered in 1863 by H. Will and W. Koerner in 1863, they found the compound to be present in mustard oil. The first synthesis of allyl cyanide was reported by A. Claus in 1864. Allyl cyanide is produced in cruciferous vegetables by myrosi ...
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Cyclopropane Carboxylic Acid
Cyclopropane carboxylic acid is the organic compound with the formula . It is the carboxylic acid derivative of cyclopropane. It can be prepared by hydrolysis of cyanocyclopropane, which is obtained by base-induced cyclization of 4-chlorobutyronitrile. Reactions Cyclopropane carboxylic acid has al pKa of 4.65, fairly typical for similar compounds. Esterification is conveniently done with Lewis acid catalysts. The compound has been used to probe the biosynthesis of ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub .... References {{Reflist Carboxylic acids Cyclopropanes ...
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Ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pungent smell. It is widely used in fertilizers, refrigerants, explosives, cleaning agents, and is a precursor for numeous chemicals. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many chemicals. In many countries, it is classified as an List of extremely hazardous substances, extremely hazardous substance. Ammonia is toxic, cau ...
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Strong Base
In chemistry, there are three definitions in common use of the word "base": '' Arrhenius bases'', '' Brønsted bases'', and '' Lewis bases''. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century. In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH−. These ions can react with hydrogen ions (H+ according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction. A base was therefore a metal hydroxide such as NaOH or Ca(OH)2. Such aqueous hydroxide solutions were also described by certain characteristic properties. They are slippery to the touch, can taste bitter and change the color of pH indicators (e.g., turn red litmus paper blue). In water, by altering the autoionization equilibrium, bases yield solutions in which the hydrogen ion activity is lower than it is in pure water, i.e., t ...
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Nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or propanenitrile). The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons. Inorganic compounds containing the group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic. Structure and basic properties The N−C−C geom ...
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4-Chlorobutyronitrile
4-Chlorobutyronitrile is the organic compound with the formula ClCH2CH2CH2CN. With both chloro and cyano functional groups, it is a bifunctional molecule. It is a colorless liquid. Synthesis It is prepared by the reaction of potassium cyanide with 1-Bromo-3-chloropropane, 1-bromo-3-chloropropane. Cyclopropyl cyanide is prepared by reaction of 4-chlorobutyronitrile with sodium amide in liquid ammonia. However an increased yield was reported when the base/solvent mixture was changed to NaOH/DMSO. Drug use 4-Chlorobutyronitrile is a precursor to the drugs buflomedil and buspirone. Precursor 4-Chlorobutyronitrile has been used as a starting material to prepare 2-phenylpyrrolidine [registry number 1006-64-0]. This in turn is a chief precursor to a family of compounds called pyrroloisoquinolines. These are valuable agents in medicinal chemistry that are endowed with BAT substrate reuptake inhibitor properties, elevating the synaptic concentration of serotonin and/or catecholamines. ...
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