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Superacids
In chemistry, a superacid (according to the original definition) is an acid with an acidity greater than that of 100% pure sulfuric acid (), which has a Hammett acidity function (''H''0) of −12. According to the modern definition, a superacid is a medium in which the chemical potential of the proton is higher than in pure sulfuric acid. Commercially available superacids include trifluoromethanesulfonic acid (), also known as triflic acid, and fluorosulfuric acid (), both of which are about a thousand times stronger (i.e. have more negative ''H''0 values) than sulfuric acid. Most strong superacids are prepared by the combination of a strong Lewis acid and a strong Brønsted acid. A strong superacid of this kind is fluoroantimonic acid. Another group of superacids, the carborane acid group, contains some of the strongest known acids. Finally, when treated with anhydrous acid, zeolites (microporous aluminosilicate minerals) will contain superacidic sites within their pores. These ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fluoroantimonic Acid
Fluoroantimonic acid is a mixture of hydrogen fluoride and antimony pentafluoride, containing various cations and anions (the simplest being and ). This mixture is a superacid stronger than pure sulfuric acid, by many orders of magnitude, according to its Hammett acidity function. It even protonates some hydrocarbons to afford pentacoordinate carbocations ( carbonium ions). Like its precursor hydrogen fluoride, it attacks glass, but can be stored in containers lined with PTFE (Teflon) or PFA. Chemical composition Fluoroantimonic acid is formed by combining hydrogen fluoride and antimony pentafluoride: :SbF5 + 2 HF + H2F+ The speciation (i.e., the inventory of components) of fluoroantimonic acid is complex. Spectroscopic measurements show that fluoroantimonic acid consists of a mixture of HF-solvated protons, – (such as ). Thus, the formula "" is a convenient but oversimplified approximation of the true composition. Nevertheless, the extreme acidity of this mixt ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Magic Acid
Magic acid () is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid () and antimony pentafluoride (). This conjugate Brønsted acid, Brønsted–Lewis acid, Lewis superacid system was developed in the 1960s by Ronald Gillespie and his team at McMaster University, and has been used by George Olah to stabilise carbocations and hypercoordination, hypercoordinated carbonium ions in liquid media. Magic acid and other superacids are also used to catalyze isomerization of saturated hydrocarbons, and have been shown to protonation, protonate even weak bases, including methane, xenon, halogens, and molecular hydrogen. History The term "superacid" was first used in 1927 when James Bryant Conant found that perchloric acid could protonate ketones and aldehydes to form salts in nonaqueous solution. The term itself was coined by R. J. Gillespie, after Conant combined sulfuric acid with fluorosulfuric acid, and found the solution to be several million ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Antimony Pentafluoride
Antimony pentafluoride is the inorganic compound with the formula Sb F5. This colorless, viscous liquid is a strong Lewis acid and a component of the superacid fluoroantimonic acid, formed upon mixing liquid HF with liquid SbF5 in 1:1 ratio. It is notable for its strong Lewis acidity and the ability to react with almost all known compounds. Preparation Antimony pentafluoride is prepared by the reaction of antimony pentachloride with anhydrous hydrogen fluoride:Sabina C. Grund, Kunibert Hanusch, Hans J. Breunig, Hans Uwe Wolf "Antimony and Antimony Compounds" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim :SbCl5 + 5 HF → SbF5 + 5 HCl It can also be prepared from antimony trifluoride and fluorine. Structure and chemical reactions In the gas phase, SbF5 adopts a trigonal bipyramidal structure of D3h point group symmetry (see picture). The material adopts a more complicated structure in the liquid and solid states. The liquid contains polymers whe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fluorosulfonic Acid
Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula . It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, , substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow.Erhardt Tabel, Eberhard Zirngiebl, Joachim Maas "Fluorosulfuric Acid" in "Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. Properties Fluorosulfuric acid is a free-flowing colorless liquid. It is soluble in polar organic solvents (e.g. nitrobenzene, acetic acid, and ethyl acetate), but poorly soluble in nonpolar solvents such as alkanes. is one of the strongest known simple Brønsted acids. It has an ''H''0 value of −15.1 compared to −12 for sulfuric acid. The combination of and the Lewis acid antimony pentafluoride produces "Magic acid", which is a far stronger protonating age ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acid
An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acid–base theory, Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Acid–base reaction#Arrhenius theory, Arrhenius acids. Johannes Nicolaus Brønsted, Brønsted and Martin Lowry, Lowry generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted–Lowry or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H+. Aqueous Arrhenius acids have characteristic properties that provide a practical description of an acid. Acids form aqueous solutions with a sour taste, can turn blue litmus red, and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Magic Acid
Magic acid () is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid () and antimony pentafluoride (). This conjugate Brønsted acid, Brønsted–Lewis acid, Lewis superacid system was developed in the 1960s by Ronald Gillespie and his team at McMaster University, and has been used by George Olah to stabilise carbocations and hypercoordination, hypercoordinated carbonium ions in liquid media. Magic acid and other superacids are also used to catalyze isomerization of saturated hydrocarbons, and have been shown to protonation, protonate even weak bases, including methane, xenon, halogens, and molecular hydrogen. History The term "superacid" was first used in 1927 when James Bryant Conant found that perchloric acid could protonate ketones and aldehydes to form salts in nonaqueous solution. The term itself was coined by R. J. Gillespie, after Conant combined sulfuric acid with fluorosulfuric acid, and found the solution to be several million ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fluorosulfuric Acid
Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula . It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, , substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow.Erhardt Tabel, Eberhard Zirngiebl, Joachim Maas "Fluorosulfuric Acid" in "Ullmann's Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. Properties Fluorosulfuric acid is a free-flowing colorless liquid. It is soluble in polar organic solvents (e.g. nitrobenzene, acetic acid, and ethyl acetate), but poorly soluble in nonpolar solvents such as alkanes. is one of the strongest known simple Brønsted acids. It has an ''H''0 value of −15.1 compared to −12 for sulfuric acid. The combination of and the Lewis acid antimony pentafluoride produces "Magic acid", which is a far stronger protonating ag ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trifluoromethanesulfonic Acid
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents. Synthesis Trifluoromethanesulfonic acid is produced industrially by electrochemical fluorination (ECF) of methanesulfonic acid CH3SO3H + 4 HF ->CF3SO2F + H2O + 3 H2 The resulting CF3SO2F is hydrolyzed, and the resulting triflate salt is reprotonated. Alternatively, trifluoromethanesulfonic acid arises by oxidation of trifluoromethylsulfenyl chloride: CF3SCl + 2 Cl2 + 3 H2O -> CF3SO3H + 5 HCl Triflic acid is purified by distillation from triflic anhydride. Historical Trifluoromethanesulfonic acid was first synthesized in 1954 by Robert Haszeldine and Kidd by the following reaction: : Reactions As an acid In the laboratory, tr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hammett Acidity Function
The Hammett acidity function (''H''0) is a measure of acidity that is used for very concentrated solutions of strong acids, including superacids. It was proposed by the physical organic chemist Louis Plack Hammett and is the best-known acidity function used to extend the measure of Brønsted–Lowry acidity beyond the dilute aqueous solutions for which the pH scale is useful. In highly concentrated solutions, simple approximations such as the Henderson–Hasselbalch equation are no longer valid due to the variations of the activity coefficients. The Hammett acidity function is used in fields such as physical organic chemistry for the study of acid-catalyzed reactions, because some of these reactions use acids in very high concentrations, or even neat (pure).Gerrylynn K. Roberts, Colin Archibald Russell. ''Chemical History: Reviews of the Recent Literature''. Royal Society of Chemistry, 2005. . Definition The Hammett acidity function, ''H''0, can replace the pH in concentrat ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbocation
Carbocation is a general term for ions with a positively charged carbon atom. In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom. They are further classified in two main categories according to the coordination number of the charged carbon: three in the carbenium ions and five in the carbonium ions. Among the simplest carbocations are the methenium (a carbenium ion), methanium (a carbonium ion), acylium ions , and Vinyl cation, vinyl cations. Until the early 1970s, carbocations were called ''carbonium ions''. This nomenclature was proposed by George Andrew Olah, G. A. Olah. Carbonium ions, as originally defined by Olah, are characterized by a Three-center two-electron bond, three-center two-electron delocalized bonding scheme and are essentially synonymous with so-called 'non-classical carbocations', which are carbocations that contain bridging C–C or C–H σ-bonds. However ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Octane Rating
An octane rating, or octane number, is a standard measure of a liquid fuel, fuel's ability to withstand Compression ratio, compression in an internal combustion engine without causing engine knocking. The higher the octane number, the more compression the fuel can withstand before detonating. Octane rating does not relate directly to the power output or the energy content of the fuel per unit mass or volume, but simply indicates the resistance to detonating under pressure without a spark. Whether a higher octane fuel improves or impairs an engine's performance depends on the design of the engine. In broad terms, fuels with a higher octane rating are used in higher-compression Petrol engine, gasoline engines, which may yield higher power for these engines. The added power in such cases comes from the way the engine is designed to compress the air/fuel mixture, and not directly from the rating of the gasoline. In contrast, fuels with lower octane (but higher cetane numbers) are idea ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
