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Extremely strong acid
In chemistry, a superacid (according to the original definition) is an acid with an acidity greater than that of 100% pure sulfuric acid (H2SO4), which
Superacid
Chemical compound
(H2F+) and fluoroantimonate (SbF−6). The mixture is the strongest known superacid, stronger than pure sulfuric acid by many orders of magnitude, according
Fluoroantimonic_acid
Superacid system prepared from a Brønsted and a Lewis superacid
Magic acid (FSO3H·SbF5) is a superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid (HSO3F) and antimony pentafluoride
Magic_acid
Class of chemical compounds
acids H(CXB 11Y 5Z 6) (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
Carborane_acid
Measure of the tendency of an acid to dissociate
protonating medium than 100% sulfuric acid and thus, by definition, a superacid. (To prevent ambiguity, in the rest of this article, "strong acid" will
Acid_strength
Chemical compound
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
Antimony_pentafluoride
Hungarian-American chemist (1927–2017)
His research involved the generation and reactivity of carbocations via superacids. For this research, Olah was awarded a Nobel Prize in Chemistry in 1994
George_Andrew_Olah
Measure of acidity for very strong acids
that is used for very concentrated solutions of strong acids, including superacids. It was proposed by the physical organic chemist Louis Plack Hammett and
Hammett_acidity_function
Monocationic atomic hydrogen, H+
stronger with nearby electrons than any partly ionized atom. Although superacids are sometimes said to owe their extraordinary hydron-donating power to
Hydron
Brand name for a chemical product
challenges in all applications due to the loss of water above 100 °C. It is a superacid catalyst. The combination of fluorinated backbone, sulfonic acid groups
Nafion
Chemical group (–OSO2CF3) or anion (charge –1)
polyatomic ion; this comes from the fact that triflic acid (CF3SO3H) is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest
Triflate
Chemical compound
CF3SO2. Abbreviated Tf2O, triflic anhydride is the acid anhydride of the superacid triflic acid, CF3SO2OH. Triflic anhydride is prepared by dehydration of
Trifluoromethanesulfonic anhydride
Trifluoromethanesulfonic_anhydride
Chemical compound giving a proton or accepting an electron pair
acidic plastic that is filterable. Superacids are acids stronger than 100% sulfuric acid. Examples of superacids are fluoroantimonic acid, magic acid
Acid
Ion of carbon with five hydrogens
atoms and one dihydrogen molecule), bearing a +1 electric charge. It is a superacid and one of the onium ions, indeed the simplest carbonium ion. It is highly
Methanium
American chemist
substituted aromatic compounds. He is also known for his research into superacids and his development of a scheme for comparing their acidities based on
Louis_Plack_Hammett
Chemical element with atomic number 51 (Sb)
monomeric. Antimony pentafluoride is a powerful Lewis acid used to make the superacid fluoroantimonic acid (H2F+·SbF−6). Oxohalides are more common for antimony
Antimony
Chemical compound (H2SO4)
esterification and dehydration of alcohols. When allowed to react with superacids, sulfuric acid can act as a base and can be protonated, forming the [H3SO4]+
Sulfuric_acid
Extremely strong base
probably the strongest base according to quantum-chemical calculations. Superacid Phosphazene Puleo, Thomas R.; Sujansky, Stephen J.; Wright, Shawn E.;
Superbase
Chemical compound
of methanol. Methyloxonium is formed when methanol is treated with a superacid which add a proton. When methanol undergoes autoprotolysis, if forms methyloxonium
Methyloxonium
Chemical compound
oxidants. Pure H[BF4] has not been described. The same holds true for the superacids that are known by the simplified formulas H[PF6] and H[SbF6]. However
Fluoroboric_acid
Chemical compound
HF is also widely used in the petrochemical industry as a component of superacids. Due to strong and extensive hydrogen bonding, it boils near room temperature
Hydrogen_fluoride
Chemical compound
highly reactive cations. Hexafluoroantimonate is the conjugate base of the superacid fluoroantimonic acid HF·SbF5. As fluoroantimonic acid is one of the strongest
Fluoroantimonate
Synthetic polymer
containers. It is used in containers for storing fluoroantimonic acid, a superacid. PTFE tubes are used in gas-gas heat exchangers in gas cleaning of waste
Polytetrafluoroethylene
Acid derived from inorganic compounds
(HNO3); these are also known as bench acids. Mineral acids range from superacids (such as perchloric acid) to very weak ones (such as boric acid). Mineral
Mineral_acid
Hydrocarbon compound (CH4) in natural gas
Methanium can also be produced as diluted solutions from methane with superacids. Cations with higher charge, such as CH62+ and CH73+, have been studied
Methane
Chemical compound
Additionally it is a useful component in etching of chrome. Perchloric acid, a superacid, is one of the strongest Brønsted–Lowry acids. That its pKa is lower than
Perchloric_acid
Chemical compound
is a far stronger protonating agent. These acids are categorized as "superacids", acids stronger than 100% sulfuric acid. Reflecting its strong acidity
Fluorosulfuric_acid
Chemical compound
Hexafluoroarsenate is relatively inert, being the conjugate base of the notional superacid hexafluoroarsenic acid (HAsF6). The first undisputed synthesis is due
Hexafluoroarsenate
Forms during electrophilic substitution on benzene ring
benzenium ion can be isolated when benzene is protonated by the carborane superacid H(CB11H(CH3)5Br6). The benzenium salt is crystalline with thermal stability
Arenium_ion
Measure of the level of acidity or basicity of an aqueous solution
the Hammett acidity function, H0, has been developed in connection with Superacids. In 2010, a new approach to measuring pH was proposed, called the unified
PH
Class of chemical compounds
boron for boron neutron capture therapy. The compound H(CHB11Cl11) is a superacid, forming an isolable salt with protonated benzene cation, [C6H7]+ (benzenium
Carborane
Chemical compound
astrophysical interest. It also exists in the condensed state when formed by superacids. In the ground state, HC+NH is a simple linear molecule, whereas its excited
Protonated_hydrogen_cyanide
Chemical compound
strong. With a Ka = 5×1014, pKa = −14.7±2.0, triflic acid qualifies as a superacid. It owes many of its useful properties to its great thermal and chemical
Triflic_acid
Aqueous cation H3O+
monomer in liquid phase was achieved in a nonaqueous, low nucleophilicity superacid solution (fluoroantimonic acid dissolved in SO2). The ion was characterized
Hydronium
George Olah, where he worked on characterizing stable carbocations in superacids. He also sits on several editorial boards of major scientific journals
G._K._Surya_Prakash
Ion with a positively charged carbon atom
methanium ion, CH5+, which is formed by protonation of methane using a superacid. By necessity of having five bonds on carbon but only four valence electron
Carbocation
Type of chemical substance
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Base_(chemistry)
Chemical compound of sulfur and oxygen
Lewis basicity, it is often used as a low-temperature solvent/diluent for superacids like magic acid (FSO3H/SbF5), allowing for highly reactive species like
Sulfur_dioxide
Chemical property
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Dissociation_constant
Chemical compound
PMID 15186185. Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers
Allyl_phenyl_ether
Chemical element with atomic number 52 (Te)
Arpad; Olah, George Andrew; Surya Prakash, G. K.; Sommer, Jean (2009). Superacid Chemistry (2nd ed.). Wiley-Interscience. pp. 444–445. ISBN 978-0-471-59668-4
Tellurium
Chemical compound
Dominik (2025). "Hexaphenyl-1,2-Diphosphonium Dication [Ph3P–PPh3]2+: Superacid, Superoxidant, or Super Reagent?". Journal of the American Chemical Society
Triphenylphosphine
Hirsutene Is also named after an animal, a goat (Hircus). Magic acid A superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric
List of chemical compounds with unusual names
List_of_chemical_compounds_with_unusual_names
Chemical reaction including condensation
conditions with strong acids like hydrochloric acid, trifluoroacetic acid or superacids. Instead of catalyzing the Pictet–Spengler cyclization with strong acid
Pictet–Spengler_reaction
Chemical compound
tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf3CH) is an organic superacid. It is one of the strongest known carbon acids and is among the strongest
Triflidic_acid
Measure of acidity
different environments, most notably the Hammett acidity function, H0, for superacid media and its modified version H− for superbasic media. The term acidity
Acidity_function
Parent chemical compound of certain fluorescent dyes
Ide, Yuki; Gao, Min; Yoneda, Tomoki; Inokuma, Yasuhide (2026-03-19). "Superacid-resistant macrocyclic BODIPYs". Nature Communications. 17 (1): 2332. doi:10
BODIPY
Process by which the human body regulates pH
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Acid–base_homeostasis
Chemical bond theory
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Lewis_acids_and_bases
Chemical group (R–C=O)
A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid". Angewandte Chemie International Edition. 60 (24): 13656–13660. doi:10
Acyl_group
Solute that (almost) completely ionizes or dissociates in solution
acid, HIO4 Fluoroantimonic acid, HSbF6 Magic acid, FSO3HSbF5 Carborane superacid, H(CHB11Cl11) Fluorosulfuric acid, FSO3H Triflic acid, CF3SO3H Strong
Strong_electrolyte
Aqueous solution of a weak acid and its conjugate base
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Buffer_solution
Measure of an acid's strength in solution
non-aqueous media, the most notable being the Hammett acidity function, H0, for superacid media and its modified version H− for superbasic media. In aprotic solvents
Acid_dissociation_constant
Organic compound (CH3–C≡N); simplest organic nitrile
forms Lewis adducts with group 13 Lewis acids like boron trifluoride. In superacids, it is possible to protonate acetonitrile. Acetonitrile is a byproduct
Acetonitrile
Chemical compound
shortened to triflimidic acid; CAS: 82113-65-3), is a commercially available superacid. It is a crystalline compound, but is hygroscopic to the point of being
Bistriflimide
Chemical compound
Coudurier, Gisele; Joly, Jean Francois; Vedrine, Jacques C. (1993). "Superacid and catalytic properties of sulfated zirconia". Journal of Catalysis.
Zirconium(IV)_hydroxide
Ion
and in plasmas that contain oxygen and hydrogen. Oxidation by O2 in superacids could be by way of the production of protonated molecular oxygen. It is
Dioxidanylium
Chemical compound
Jean (2009). "3.1.2. Observation of Stable, Long-Lived Carbocations". Superacid Chemistry (2nd ed.). Wiley. pp. 84–85. ISBN 978-0-471-59668-4. Schneider
Isopropyl_fluoride
Chemical reaction between an acid and a base
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Acid–base_reaction
Chemical bond
A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid". Angew. Chem. Int. Ed. 60 (24): 13656–13660. doi:10.1002/anie.202103414
Carbon–oxygen_bond
acid (H2SO4) is a strong acid in water but behaves more like a base in superacids. amyl A common non-systematic name for a pentyl group. analyte The specific
Glossary_of_chemistry_terms
Chemical compound
Peter Forgo, Árpad Molnár (2007), Fused polycyclic hydrocarbons through superacid-induced cyclialkylation of aromatics. Catalysis Letters, volume 119, pages
2,2,5,5-Tetramethyltetrahydrofuran
2,2,5,5-Tetramethyltetrahydrofuran
Chemical compound
and alkenes and for the protonation of aromatic compounds. The TaF5–HF superacid system is stable in reducing environments, unlike SbF5–HF. In the presence
Tantalum(V)_fluoride
Any chemical compound having at least one fluorine atom
(R-12 refrigerant), a CFC Trifluoromethanesulfonic acid (triflic acid), a superacid Perfluorooctanesulfonic acid, a fluorosurfactant (the anion is depicted)
Fluorine_compounds
Chemical compound
and aromatic stabilization of its anion, pentacyanocyclopentadiene is a superacid, with an estimated aqueous pKa of −11. The free acid was prepared by Reed
Pentacyanocyclopentadiene
Milligrams of a base needed to neutralize 1 gram of a given acid
"Biodiesel production from high acid value waste frying oil catalyzed by superacid heteropolyacid". Biotechnology and Bioengineering. 101 (1): 93–100. doi:10
Acid_value
Chemical group derived from alkanes (one hydrogen removed)
years" have been prepared. Typically alkyl cations are generated using superacids and alkyl anions are observed in the presence of strong bases. Alkyl radicals
Alkyl_group
Chemical compound
Mitzel, Norbert W. (2017-06-09). "Tris(perfluorotolyl)borane-A Boron Lewis Superacid". Angewandte Chemie International Edition. 56 (29): 8578–8582. doi:10
Tris(pentafluorophenyl)borane
Type of oxide
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Acidic_oxide
Description of a molecule's true bond structure as a combination of structures
position in some of the product. This and other evidence (such as NMR in superacid solutions) shows that the intermediate carbocation must have a highly
Resonance_(chemistry)
Autoprotolysis or exchange of a proton between two water molecules
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Self-ionization_of_water
Form of carbon with an extremely high surface area
reported about synthesis of activated carbon with chemically grafted superacid sites –CF2SO3H. Some of the chemical properties of activated carbon have
Activated_carbon
Acid that is insoluble in the reaction medium
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Solid_acid
thermodynamically quite stable. However, their stability in solution depends on the superacid solvent. For example, [I2]+ is stable in fluoroantimonic acid (HF with
Polyhalogen_ions
Ion
Ramírez-Solís, Alejandro; Mota, Claudio J. A. (March 2002). "The Nature of Superacid Electrophilic Species in HF/SbF5: A Density Functional Theory Study".
Fluoronium
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Organic_base
Chemical theory about acids and bases
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Brønsted–Lowry acid–base theory
Brønsted–Lowry_acid–base_theory
Chemical compound
The helium hydride ion, hydridohelium(1+) ion, or helonium is a cation (positively charged ion) with chemical formula HeH+. It consists of a helium atom
Helium_hydride_ion
Chemical compound
Retrieved 2021-04-08. Arpad Molnar; G. K. Surya Prakash; Jean Sommer (2009). Superacid Chemistry (2nd ed.). Wiley-Interscience. p. 44. ISBN 978-0-471-59668-4
Hexafluorophosphoric_acid
Pharmaceutical drug
S. (1 September 1999). "Synthesis of Aryl-Substituted Piperidines by Superacid Activation of Piperidones". The Journal of Organic Chemistry. 64 (18):
Budipine
Anion with the chemical formula PF6–
incompatibility (help) Molnar, A.; Surya Prakash, G. K.; Sommer, J. (2009). Superacid Chemistry (2nd ed.). Wiley-Interscience. p. 44. ISBN 978-0-471-59668-4
Hexafluorophosphate
Asymmetric catalyst derived from proline
reaction with Grignard reagent 3c and proline ester 3b. A Lewis acid superacid salt (6) can be obtained with the aid of triflic acid (5). Many other
CBS_catalyst
Chemical property of reacting with either an acid or base
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Amphoterism
through partial sigma bonds. While best observable in the presence of superacids at room temperature, spectroscopic evidence has suggested that hydrogen-bridged
Hydrogen-bridged_cations
Topics referred to by the same term
Wu-Tang Clan A short term for triflic or trifluoromethanesulfonic acid, a superacid This disambiguation page lists articles associated with the title Trife
Trife
Chemical species that accepts an electron pair from a nucleophile
electrophilic reagents with greatly enhanced reactivities in the presence of superacids. These compounds were first described by George A. Olah. Superelectrophiles
Electrophile
Class of compounds of boron
Carboranes Azaboranes Metallaboranes Metallacarboranes Dicarbollide Carborane superacid Koeritz, Mason T.; Banovetz, Haley K.; Prell, Sean A.; Stanley, Levi M
Heteroborane
Molecule with three connected cyclohexane rings arranged in the "armchair" configuration
synthesis yield was later increased to 60% and 98% by ultrasound and superacid catalysis. Today, adamantane is an affordable chemical compound with a
Adamantane
Type of nonaqueous solvents
relies on amine solvents. The combination of HF and SbF5 is the basis of a superacid solution. Using this mixture, the conjugate acid of hydrogen sulfide can
Inorganic_nonaqueous_solvent
Chemical compound
argon is 369 kJ/mol, less than that of dihydrogen. This makes ArH+ a superacid capable of exothermic protonation of H2 and various neutral free radical
Argonium
chemist who worked on the generation and reactivity of carbocations via superacids; 1994 Nobel Prize in Chemistry Marilyn Olmstead (1943–2020), American
List_of_chemists
Chemical added to show pH of a solution
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
PH_indicator
Group of isomeric chemical compounds which are strong bases
All three isomers function as superbases better than helonium does as a superacid. Lithium monoxide anion Poad, Berwyck L. J.; Reed, Nicholas D.; Hansen
Diethynylbenzene_dianion
Measure of Lewis basicity
ECW model Acid types Brønsted–Lowry Lewis Mineral Organic Oxide Strong Superacids Weak Solid Base types Brønsted–Lowry Lewis Organic Oxide Strong Superbases
Donor_number
Chemical compound
Chlorosulfuric acid (IUPAC name: sulfurochloridic acid) is the inorganic compound with the formula HSO3Cl. It is also known as chlorosulfonic acid, being
Chlorosulfuric_acid
Type of saturated hydrocarbon compound
no observable protonation in pure sulfuric acid (H0 ~ −12), although superacids that are at least millions of times stronger have been known to protonate
Alkane
Anion which interacts weakly with cations
as ligands. Non-coordinating anions are important components of many superacids, which result from the combination of Brønsted acids and Lewis acids.
Non-coordinating_anion
Class of Chemical Compounds
Rettig, Steven J.; Trotter, James; Aubke, Friedhelm (January 1996). "Superacid Anions: Crystal and Molecular Structures of Oxonium Undecafluorodiantimonate(V)
Fluorosulfates
Any chemical compound having at least one boron atom
be halogenated to form reactive structures including carborane acid, a superacid. As one example, carboranes form useful molecular moieties that add considerable
Boron_compounds
Coordination complexes of transition metals and metal ions with carbon monoxide ligands
carbonyl complex [Pt(CO)4]2+ can be prepared by working in so-called superacids such as antimony pentafluoride. Although CO is considered generally as
Metal_carbonyl
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