The RXNO Ontology is a formal

ontology Ontology is the philosophical study of existence, being. It is traditionally understood as the subdiscipline of metaphysics focused on the most general features of reality. As one of the most fundamental concepts, being encompasses all of realit ...

of chemical named reactions. It was originally developed at the

Royal Society of Chemistry The Royal Society of Chemistry (RSC) is a learned society and professional association in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the ...

(RSC) and is associated with the Open Biomedical Ontologies Foundry. The RXNO ontology unifies several previous attempts to systematize chemical reactions including the

Merck Index ''The Merck Index'' is an encyclopedia of chemical substance, chemicals, pharmaceutical drug, drugs and biomolecule, biologicals with over 10,000 monographs on single substances or groups of related chemical compound, compounds published online ...

and the hierarchy of Carey, Laffan, Thomson and Williams.

Major Reaction Categories

The twelve top-level reaction categories proposed by Carey, Laffan, Thompson and Williams are given in the table below, together with their RXNO ontology identifiers and the equivalent Wikipedia categories where applicable.

Name Reactions

The following table lists the RXNO identifiers for some example

name reaction A name reaction (or named reaction) is a chemical reaction named after its discoverer(s) or developer(s). Among the tens of thousands of organic reactions that are known, hundreds of such reactions are typically identified by the eponym. Well-know ...

s. :RXNO:0000003

Perkin reaction The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin in 1868 that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensati ...

:RNXO:0000006

Diels–Alder reaction In organic chemistry, the Diels–Alder reaction is a chemical reaction between a Conjugated system, conjugated diene and a substituted alkene, commonly termed the Diels–Alder reaction#The dienophile, dienophile, to form a substituted cyclohexe ...

:RXNO:0000014

Grignard reaction The Grignard reaction () is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...

:RXNO:0000015

Wittig reaction The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most o ...

:RXNO:0000021

Sandmeyer reaction The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides ...

:RXNO:0000024

Heck reaction The Heck reaction (also called the Mizoroki–Heck reaction) is the chemical reaction of an unsaturated halide (or triflate) with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after T ...

:RXNO:0000026

Beckmann rearrangement The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement reaction, rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on ...

:RXNO:0000028

Cope rearrangement A cope ( ("rain coat") or ("cape")) is a liturgical long mantle or cloak, open at the front and fastened at the breast with a band or clasp. It may be of any liturgical colour. A cope may be worn by any rank of the Catholic or Anglican cler ...

:RXNO:0000031

Baeyer–Villiger oxidation The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first ...

:RXNO:0000042

Birch reduction The Birch reduction or Metal-Ammonia reduction is an organic reaction that is used to convert arenes to Cyclohexa-1,4-diene, 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch (organic chemist), Arthur Birch and i ...

:RXNO:0000043

Claisen condensation The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. It is named ...

:RXNO:0000056

Horner–Wadsworth–Emmons reaction The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. In 1958, Leopold Horner published a modifie ...

:RXNO:0000062

Skraup reaction The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850–1910). In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing a ...

:RXNO:0000064

Fischer indole synthesis The Fischer indole synthesis is a chemical reaction that produces the aromatic Heterocyclic compound, heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by ...

:RXNO:0000074

Wurtz reaction In organic chemistry, the Wurtz reaction, named after Charles Adolphe Wurtz, is a coupling reaction in which two alkyl halides are treated with sodium metal to form a higher alkane. : 2 R−X + 2 Na → R−R + 2 NaX The reaction is of little val ...

:RXNO:0000081

Ullmann condensation The Ullmann condensation or Ullmann-type reaction is the copper-promoted conversion of aryl halides to aryl ethers, aryl thioethers, aryl nitriles, and aryl amines. These reactions are examples of cross-coupling reactions. Ullmann-type reaction ...

:RXNO:0000084

Barbier reaction The Barbier reaction is an organometallic reaction between an alkyl halide (chloride, bromide, iodide), a carbonyl group and a metal. The reaction can be performed using magnesium, aluminium, zinc, indium, tin, samarium, barium or their salts. ...

:RXNO:0000088

Negishi coupling The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon–carbon bonds (C–C) in the process. A palladium (0) s ...

:RXNO:0000090

Williamson ether synthesis The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ...

:RXNO:0000098

Glaser coupling The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional oxidant like air. The base used in the original ...

:RXNO:0000103

Gabriel synthesis The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel. The Gabriel reacti ...

:RXNO:0000106

Hunsdiecker reaction The Hunsdiecker reaction (also called the Borodin reaction or the Hunsdiecker–Borodin reaction) is a name reaction in organic chemistry whereby silver salts of carboxylic acids react with a halogen to produce an organic halide. It is an ex ...

:RXNO:0000140

Suzuki reaction The Suzuki reaction or Suzuki coupling is an organic reaction that uses a palladium complex catalyst to cross-couple a boronic acid to an organohalide. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemi ...

:RXNO:0000147

Emde degradation The Emde degradation (also called Emde-reaction or Emde-reduction) is a method for the reduction of a quaternary ammonium cation to a tertiary amine with sodium amalgam: This organic reaction was first described in 1909 by the German chemist He ...

:RXNO:0000148

Claisen rearrangement The Claisen rearrangement is a powerful carbon–carbon chemical bond, bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl Vinyl group, vinyl ether will initiate a Sigmatropic reaction, ,3sigmatropic r ...

:RXNO:0000156

Lossen rearrangement The Lossen rearrangement is the conversion of a hydroxamic acid, hydroxamate ester to an isocyanate. Typically O-acyl, sulfonyl, or phosphoryl O-derivative are employed. The isocyanate can be used further to generate ureas in the presence of ami ...

:RXNO:0000157

Nef reaction In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane () to an aldehyde () or a ketone () and nitrous oxide (). The reaction has been the subject of several ...

:RXNO:0000183

Perkow reaction The Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a dialkyl vinyl group, vinyl phosphate and an alkyl halide. In the related Michaelis–Arbuzov reaction the same reactants are known ...

:RXNO:0000193

Hiyama coupling The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Ha ...

:RXNO:0000210

Fleming–Tamao oxidation The Fleming–Tamao oxidation, or Tamao–Kumada–Fleming oxidation, converts a carbon–silicon bond to a carbon–oxygen bond with a peroxy acid or hydrogen peroxide. Fleming–Tamao oxidation refers to two slightly different conditions develop ...

:RXNO:0000218

Cannizzaro reaction The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid. ...

:RXNO:0000288

Rosenmund–von Braun reaction The Rosenmund–von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to yield an aryl nitrile. : The reaction was named after Karl Wilhelm Rosenmund who together with his Ph.D. student Erich Struck disc ...

:RXNO:0000369

Friedel–Crafts reaction The Friedel–Crafts reactions are a set of organic reaction, reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an Aromatic hydrocarbon, aromatic ring. Friedel–Crafts reactions are of two main types: alky ...

:RXNO:0000444

Fries rearrangement The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenolic ester to a Hydroxyl, hydroxy aryl ketone by catalysis of Lewis acids. It involves migration of an acyl group of phenol ester to t ...

:RXNO:0000550

Collins oxidation The Collins oxidation is an organic reaction for the oxidation of primary alcohols to aldehydes. It is distinguished from other chromium oxide-based oxidations by the use of Collins reagent, a complex of chromium(VI) oxide with pyridine in dic ...

References

{{reflist

External links

RXNO trunk on github

RXNO at the RSC
Ontology (information science)

Major Reaction Categories

Name Reactions

See also

References

External links