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Nitronium
The nitronium ion, , is a cation. It is an onium ion because its nitrogen atom has +1 charge, similar to ammonium ion . It is created by the removal of an electron from the paramagnetic nitrogen dioxide molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ... , or the protonation of nitric acid (with removal of ). It is stable enough to exist in normal conditions, but it is generally reactive and used extensively as an electrophile in the nitration of other substances. The ion is generated '' in situ'' for this purpose by mixing concentrated sulfuric acid and concentrated nitric acid according to the equilibrium: : Structure The nitronium ion is isoelectronic with carbon dioxide and has the same linear structure and bond angle of 180°. For this reason it has ...
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Nitronium Perchlorate
Nitronium perchlorate, NO2ClO4, also known as nitryl perchlorate and nitroxyl perchlorate, is an inorganic chemical, the Salt (chemistry), salt of the perchlorate anion and the nitronium ion, nitronium cation. It forms colorless monoclinic crystals. It is hygroscopic, and is a strong oxidizing and nitrating agent. It may become hypergolic in contact with organic materials. Nitronium perchlorate was investigated as an oxidizer in solid rocket propellants. Thomas N. Scortia filed for patent on such propellant in 1963, however, its reactivity and incompatibility with many materials hindered such use. Coating of nitronium perchlorate particles with ammonium nitrate, prepared in situ by passing of dry ammonia gas over the particles, was investigated, and a patent was awarded. The decomposition rate of nitronium perchlorate can be altered by doping with Polyvalency (chemistry), multivalent cations. Nitronium perchlorate and ammonium perchlorate do not produce smoke when stoichiometri ...
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Dinitrogen Pentoxide
Dinitrogen pentoxide (also known as nitrogen pentoxide or nitric anhydride) is the chemical compound with the formula . It is one of the binary nitrogen oxides, a family of compounds that contain only nitrogen and oxygen. It exists as colourless crystals that sublime slightly above room temperature, yielding a colorless gas.Connell, Peter Steele. (1979) The Photochemistry of Dinitrogen Pentoxide'. Ph. D. thesis, Lawrence Berkeley National Laboratory. Dinitrogen pentoxide is an unstable and potentially dangerous oxidizer that once was used as a reagent when dissolved in chloroform for nitrations but has largely been superseded by nitronium tetrafluoroborate (). is a rare example of a compound that adopts two structures depending on the conditions. The solid is a salt, nitronium nitrate, consisting of separate nitronium cations and nitrate anions ; but in the gas phase and under some other conditions it is a covalently-bound molecule. History was first reported by the Fre ...
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Electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively Electric charge, charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through Addition reaction, addition and Substitution reaction, substitution reactions. Frequently seen electrophiles in Organic synthesis, organic syntheses include cations such as Hydrogen ion, H+ and nitrosonium, NO+, polarized neutral molecules such as hydrogen chloride, HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as chlorine, Cl2 and bromine, Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and Radical (chemistry), radicals, and some Lewis acids such as Borane, BH3 and Di ...
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Nitronium Tetrafluoroborate
Nitronium tetrafluoroborate is an inorganic compound with formula NO2BF4. It is a salt of nitronium cation and tetrafluoroborate anion. It is a colorless crystalline solid, which reacts with water to form the corrosive acids HF and HNO3. As such, it must be handled under water-free conditions. It is sparsely soluble in many organic solvents. Preparation Nitronium tetrafluoroborate can be prepared by adding a mixture of anhydrous hydrogen fluoride and boron trifluoride to a nitromethane solution of nitric acid or dinitrogen pentoxide. Applications Nitronium tetrafluoroborate is used in organic synthesis as an electrophilic nitrating agent and a mild oxidant An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or "Electron acceptor, accepts"/"receives" an electron from a (called the , , or ''electr .... References Tetrafluoroborates Nitronium compounds {{ino ...
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Nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol (chemistry), alcohols and nitric acid (as occurs in the Organic synthesis, synthesis of nitroglycerin). The difference between the resulting molecular structures of nitro compounds and nitrates () is that the nitrogen atom in nitro compounds is directly Chemical bond, bonded to a non-oxygen atom (typically carbon or another nitrogen atom), whereas in nitrate esters (also called organic nitrates), the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group). There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of nitroaromatic compounds such as nitrobenzene. The technology is long-standing and mature. : Nitration rea ...
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Onium Ion
In chemistry, an onium ion is a cation formally obtained by the protonation of mononuclear parent hydride of a pnictogen (group 15 of the periodic table), chalcogen (group 16), or halogen (group 17). The oldest-known onium ion, and the namesake for the class, is ammonium, , the protonated derivative of ammonia, . The name onium is also used for cations that would result from the substitution of hydrogen atoms in those ions by other groups, such as organic groups, or halogens; such as tetraphenylphosphonium, . The substituent groups may be divalent or trivalent, yielding ions such as iminium and nitrilium. A simple onium ion has a charge of +1. A larger ion that has two onium ion subgroups is called a double onium ion, and has a charge of +2. A triple onium ion has a charge of +3, and so on. Compounds of an onium cation and some other anion are known as onium compounds or onium salts. Onium ions and onium compounds are inversely analogous to ions and ate complexe ...
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Nitrogen Dioxide
Nitrogen dioxide is a chemical compound with the formula . One of several nitrogen oxides, nitrogen dioxide is a reddish-brown gas. It is a paramagnetic, bent molecule with C2v point group symmetry. Industrially, is an intermediate in the synthesis of nitric acid, millions of tons of which are produced each year, primarily for the production of fertilizers. Nitrogen dioxide is poisonous and can be fatal if inhaled in large quantities. Cooking with a gas stove produces nitrogen dioxide which causes poorer indoor air quality. Combustion of gas can lead to increased concentrations of nitrogen dioxide throughout the home environment which is linked to respiratory issues and diseases. The LC50 ( median lethal dose) for humans has been estimated to be 174 ppm for a 1-hour exposure. It is also included in the NOx family of atmospheric pollutants. Properties Nitrogen dioxide is a reddish-brown gas with a pungent, acrid odor above and becomes a yellowish-brown liquid below . ...
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Nitric Acid
Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% , it is referred to as ''fuming nitric acid''. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%. Nitric acid is the primary reagent used for nitration – the addition of a nitro group, typically to an organic molecule. While some resulting nitro compounds are shock- and thermally-sensitive explosives, a few are stable enough to be used in munitions and demolition, while others are still more stable and used as synthetic dyes and medicines (e.g. metronidazole). Nitric acid is ...
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Sulfuric Acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, and hydrogen, with the molecular formula . It is a colorless, odorless, and Viscosity, viscous liquid that is Miscibility, miscible with water. Pure sulfuric acid does not occur naturally due to its Dehydration reaction, strong affinity to water vapor; it is Hygroscopy, hygroscopic and readily absorbs water vapor from the Atmosphere of Earth, air. Concentrated sulfuric acid is a strong oxidant with powerful dehydrating properties, making it highly corrosive towards other materials, from rocks to metals. Phosphorus pentoxide is a notable exception in that it is not dehydrated by sulfuric acid but, to the contrary, dehydrates sulfuric acid to sulfur trioxide. Upon addition of sulfuric acid to water, a considerable amount of heat is releas ...
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Nitrate
Nitrate is a polyatomic ion with the chemical formula . salt (chemistry), Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are solubility, soluble in water. An example of an insoluble nitrate is bismuth oxynitrate. Chemical structure The nitrate anion is the conjugate acid, conjugate base of nitric acid, consisting of one central nitrogen atom surrounded by three identically bonded oxygen atoms in a trigonal planar arrangement. The nitrate ion carries a formal charge of −1. This charge results from a combination formal charge in which each of the three oxygens carries a − charge, whereas the nitrogen carries a +1 charge, all these adding up to formal charge of the polyatomic nitrate ion. This arrangement is commonly used as an example of Resonance (chemistry), resonance. Like the isoelectronic carbonate ion, the nitrate ion can be represented by three resonance structures: Che ...
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Nitrosonium
The nitrosonium ion is , in which the nitrogen atom is bonded to an oxygen atom with a bond order of 3, and the overall diatomic species bears a positive charge. It can be viewed as nitric oxide with one electron removed. This ion is usually obtained as the following salts: , ( nitrosylsulfuric acid, more descriptively written ) and . The and salts are slightly soluble in acetonitrile . NOBF4 can be purified by sublimation at 200–250 °C and . Synthesis and spectroscopy is isoelectronic with CO, and . It arises via protonation of nitrous acid: :HONO + H+ NO+ + H2O In its infrared spectrum of its salts, νNO is a strong peak in the range 2150-2400 cm−1. Chemical properties Hydrolysis reacts readily with water to form nitrous acid: : For this reason, nitrosonium compounds must be protected from water or even moist air. With base, the reaction generates nitrite: : As a diazotizing agent reacts with aryl amines, , to give diazonium salts, . The resu ...
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Nitryl Chloride
Nitryl chloride is a volatile inorganic compound with formula ClNO2. At standard conditions it is a gas. Formation Nitryl chloride can be formed in the reaction of dinitrogen pentoxide with chlorides or hydrogen chloride: :N2O5 + 2HCl → 2ClNO2 + H2O :N2O5 + NaCl → ClNO2 + NaNO3 Reactions Nitryl chloride adds to olefins in a radical reaction A free-radical reaction is any chemical reaction involving free radicals. This reaction type is abundant in organic reactions. Two pioneering studies into free radical reactions have been the discovery of the triphenylmethyl radical by Moses Gomb .... References {{Cite book , last=Stacey , first=F. W. , title=Organic Reactions , title-link=Organic Reactions , last2=Harris , first2=((J. F., Jr.)) , date=2004-04-30 , publisher=Wiley , isbn=978-0-471-26418-7 , editor-last=Denmark , editor-first=Scott E. , edition=1 , language=en , chapter=Formation of carbon-hetero atom bonds by free-radical chain additions to carbon-carbo ...
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