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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 In highly concentrated solutions, simple approximations such as the Henderson–Hasselbalch equation are no longer valid due to the variations of the activity coefficients.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 ...
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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 ...
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Protonating
In chemistry, protonation (or hydronation) is the adding of a proton (or hydron, or hydrogen cation), usually denoted by H+, to an atom, molecule, or ion, forming a conjugate acid. (The complementary process, when a proton is removed from a Brønsted–Lowry acid, is deprotonation.) Some examples include * The protonation of water by sulfuric acid: *: H2SO4 + H2O H3O+ + * The protonation of isobutene in the formation of a carbocation: *: (CH3)2C=CH2 + HBF4 (CH3)3C+ + * The protonation of ammonia in the formation of ammonium chloride from ammonia and hydrogen chloride: *: NH3( g) + HCl( g) → NH4Cl( s) Protonation is a fundamental chemical reaction and is a step in many stoichiometric and catalytic processes. Some ions and molecules can undergo more than one protonation and are labeled polybasic, which is true of many biological macromolecules. Protonation and deprotonation (removal of a proton) occur in most acid–base reactions; they are the core of most acid–base reac ...
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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 ...
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Oleum
Oleum (Latin ''oleum'', meaning oil), or fuming sulfuric acid, is a term referring to solutions of various compositions of sulfur trioxide in sulfuric acid, or sometimes more specifically to disulfuric acid (also known as pyrosulfuric acid). Oleums can be described by the formula ''y''SO3·H2O where ''y'' is the total molar mass of sulfur trioxide content. The value of ''y'' can be varied, to include different oleums. They can also be described by the formula H2SO4·''x''SO3 where ''x'' is now defined as the molar free sulfur trioxide content. Oleum is generally assessed according to the free SO3 content by mass. It can also be expressed as a percentage of sulfuric acid strength; for oleum concentrations, that would be over 100%. For example, 10% oleum can also be expressed as H2SO4·''0.13611''SO3, ''1.13611''SO3·H2O or 102.25% sulfuric acid. The conversion between % acid and % oleum is: :\%\,\text = 100 + \frac \times \%\,\text For ''x'' = 1 and ''y'' = 2 the empirical formul ...
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Chlorosulfuric Acid
Chlorosulfuric acid (IUPAC name: sulfurochloridic acid) is the inorganic compound with the formula HSO3Cl. It is also known as chlorosulfonic acid, being the sulfonic acid of chlorine. It is a distillable, colorless liquid which is hygroscopic and a powerful lachrymator. Commercial samples usually are pale brown or straw colored. Salts and esters of chlorosulfuric acid are known as chlorosulfates. Structure and properties Chlorosulfuric acid is a tetrahedral molecule. Its structure was debated for many decades until in 1941 Shrinivasa Dharmatti proved by magnetic susceptibility that chlorine is directly bonded to sulfur. The formula is more descriptively written SO2(OH)Cl, but HSO3Cl is traditional. It is an intermediate, chemically and conceptually, between sulfuryl chloride (SO2Cl2) and sulfuric acid (H2SO4). The compound is rarely obtained pure. Upon standing with excess sulfur trioxide, it decomposes to pyrosulfuryl chlorides: :2 ClSO3H + SO3 → H2SO4 + S2O5Cl2 Synt ...
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Triflic 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, trif ...
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Perchloric Acid
Perchloric acid is a mineral acid with the formula H Cl O4. It is an oxoacid of chlorine. Usually found as an aqueous solution, this colorless compound is a stronger acid than sulfuric acid, nitric acid and hydrochloric acid. It is a powerful oxidizer when hot, but aqueous solutions up to approximately 70% by weight at room temperature are generally safe, only showing strong acid features and no oxidizing properties. Perchloric acid is useful for preparing perchlorate salts, especially ammonium perchlorate, an important rocket fuel component. Perchloric acid is dangerously corrosive and readily forms potentially explosive mixtures. History Perchloric acid was first synthesized (together with potassium perchlorate) by Austrian chemist and called "oxygenated chloric acid" in mid-1810s. French pharmacist Georges-Simon Serullas introduced the modern designation along with discovering its solid monohydrate, which he mistook for an anhydride. Berzelius produced dilute perchloric acid ...
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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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Methanesulfonic Acid
Methanesulfonic acid (MsOH, MSA) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula and structure . It is the simplest of the alkylsulfonic acids (). Salts and esters of methanesulfonic acid are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate). It is hygroscopic in its concentrated form. Methanesulfonic acid can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric acid (HCl) or sulfuric acid (). History and synthesis Early history German chemist Hermann Kolbe discovered MSA between 1842 and 1845 and originally termed it methyl hyposulphuric acid. The discovery stemmed from earlier work by Berzelius and Marcet in 1813, who treated carbon disulfide with moist chlorine and produced a compound they named "sulphite of chloride of carbon". By reacting it with barium hydroxide Kolbe demonstrated it to actually be trichloromethylsul ...
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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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Phosphoric Acid
Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, which is a colourless, odourless, and non- volatile syrupy liquid. It is a major industrial chemical, being a component of many fertilizers. The compound is an acid. Removal of all three ions gives the phosphate ion . Removal of one or two protons gives dihydrogen phosphate ion , and the hydrogen phosphate ion , respectively. Phosphoric acid forms esters, called organophosphates. The name "orthophosphoric acid" can be used to distinguish this specific acid from other " phosphoric acids", such as pyrophosphoric acid. Nevertheless, the term "phosphoric acid" often means this specific compound; and that is the current IUPAC nomenclature. Production Phosphoric acid is produced industrially by one of two routes, wet processes and dry. ...
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Trifluoroacetic Acid
Trifluoroacetic acid (TFA) is a synthetic organofluorine compound with the chemical formula CF3CO2H. It belongs to the subclass of per- and polyfluoroalkyl substances (PFASs) known as ultrashort-chain perfluoroalkyl acids (PFAAs). TFA is not produced biologically or abiotically and is commonly used in organic chemistry for various purposes. It is the most abundant PFAS found in the environment. It is a haloacetic acid, with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms. It is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, ''K''a, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. Synthesis TFA is prepared industrially by the electrofluorination of ac ...
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