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Oxatriquinane
Oxatriquinane (oxoniaperhydrotriquinacene) is an alkyl oxonium ion with formula (CH2CH2CH)3O+. It has a cyclononane backbone, with a trivalent oxygen connected to carbon 1, 4, and 7, forming three fused pentagonal rings. In contrast to most trialkyloxonium ions, oxatriquinane hydrolyzes slowly. History Oxatriquinane was first described in 2008. It five-step synthesis starts from 1,4,7-cyclononatriene. Ita C–O bond lengths are 1.54 Å. The C−O−C angles are also acute. Reactions Oxonium ions normally are strong alkylating agents and are hydrolytically sensitive. Oxatriquinane does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger nucleophiles such as hydroxide, cyanide, and azide. The ability of the oxygen to enter into a fourth covalent bond has been of some theoretical interest and was achieved using carborane acid. As illustrated by the structures of most metal oxides, oxygen compounds rout ...
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Oxatriquinacene
Oxatriquinacene is an organic cation with formula . It is an oxonium ion, with a trivalent oxygen atom with +1 charge connected to carbons 1,4, and 7 of a cyclononatriene ring, forming three fused pentagonal cycles. The compound may possess weak tris-homoaromatic character. Oxatriquinacene has remarkable stability compared to other oxonium cations, although not as extreme as that of the similar oxatriquinane. It reacts with water, but can be dissolved in acetonitrile. It is of interest as a possible precursor to oxaacepentalene, a hypothetical neutral aromatic species. Oxatriquinacene was obtained in 2008 by Mascal and coworkers, through a variant of the synthesis that led them to oxatriquinane. See also * Triethyloxonium tetrafluoroborate * Brookhart's acid * Pyrylium salt Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in ...
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Oxonium Ion
In chemistry, an oxonium ion is any cation containing an oxygen atom that has three bonds and 1+ formal charge. The simplest oxonium ion is the hydronium ion (). Alkyloxonium Hydronium is one of a series of oxonium ions with the formula R''n''H3−''n''O+. Oxygen is usually pyramidal with an sp3 hybridization. Those with ''n'' = 1 are called primary oxonium ions, an example being protonated alcohol (e.g. methanol). In acidic media, the oxonium functional group produced by protonating an alcohol can be a leaving group in the E2 elimination reaction. The product is an alkene. Extreme acidity, heat, and dehydrating conditions are usually required. Other hydrocarbon oxonium ions are formed by protonation or alkylation of alcohols or ethers (R−C−−R1R2). Secondary oxonium ions have the formula R2OH+, an example being protonated ethers. Tertiary oxonium ions have the formula R3O+, an example being trimethyloxonium. Tertiary alkyloxonium salts are useful alkylatin ...
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Cyclononane
Cyclononane is an alicyclic In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. The ... hydrocarbon consisting of a ring of nine carbon atoms. Its molecular formula is C9H18. References Cycloalkanes Nine-membered rings {{hydrocarbon-stub ...
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Oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is Earth's most abundant element, and after hydrogen and helium, it is the third-most abundant element in the universe. At standard temperature and pressure, two atoms of the element bind to form dioxygen, a colorless and odorless diatomic gas with the formula . Diatomic oxygen gas currently constitutes 20.95% of the Earth's atmosphere, though this has changed considerably over long periods of time. Oxygen makes up almost half of the Earth's crust in the form of oxides.Atkins, P.; Jones, L.; Laverman, L. (2016).''Chemical Principles'', 7th edition. Freeman. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates, ...
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Carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three isotopes occur naturally, C and C being stable, while C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity. Carbon is the 15th most abundant element in the Earth's crust, and the fourth most abundant element in the universe by mass after hydrogen, helium, and oxygen. Carbon's abundance, its unique diversity of organic compounds, and its unusual ability to form polymers at the temperatures commonly encountered on Earth, enables this element to serve as a common element of all known life. It is the second most abundant element in the human body by mass (about 18.5%) after oxygen. The atoms of carbon ...
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Alkylating Agent
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion ( carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent b ...
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Nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. ''Nucleophilic'' describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. History The terms ''nucleophile'' and '' electrophile'' were introduced by Christopher Kelk Ingold in 1933, replacing the terms ''anionoid'' and ''catio ...
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Carborane Acid
Carborane acids (X, Y, Z = H, Alk, F, Cl, Br, CF3) are a class of superacids, some of which are estimated to be at least one million times stronger than 100% pure sulfuric acid in terms of their Hammett acidity function values (''H''0 ≤ –18) and possess computed p''K''a values well below –20, establishing them as some of the strongest known Brønsted acids. The best-studied example is the highly chlorinated derivative . The acidity of was found to vastly exceed that of triflic acid, , and bistriflimide, , compounds previously regarded as the strongest isolable acids. Their high acidities stem from the extensive delocalization of their conjugate bases, carboranate anions (CXB11Y5Z6−), which are usually further stabilized by electronegative groups like Cl, F, and CF3. Due to the lack of oxidizing properties and the exceptionally low nucleophilicity and high stability of their conjugate bases, they are the only superacids known to protonate C60 fullerene without decompo ...
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Metal Oxide
An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the Earth's crust consists of oxides. Even materials considered pure elements often develop an oxide coating. For example, aluminium foil develops a thin skin of Al2O3 (called a passivation layer) that protects the foil from further corrosion.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. . Stoichiometry (the measurable relationship between reactants and chemical equations of a equation or reaction) Oxides are extraordinarily diverse in terms of stoichiometries and in terms of the structures of each stoichiometry. Most elements form oxides of more than one stoichiometry. A well known example is carbon monoxide and carbon dioxide.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry ...
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Oxonium Compounds
Oxonium may refer to: *Oxonium ion, any ion which contains a trivalent oxygen atom, *Oxonium, an IUPAC name for the simplest oxonium ion, hydronium, *''Oxonium'' (often abbreviated to ''Oxon.''), sometimes used in university circles as a Latin name for Oxford University Oxford () is a city in England. It is the county town and only city of Oxfordshire. In 2020, its population was estimated at 151,584. It is north-west of London, south-east of Birmingham and north-east of Bristol. The city is home to the Un ...
in England {{Disambiguation ...
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