The structure of a nitrile: the functional group is highlightedblue
Inorganic chemistry, anitrile is anyorganic compound that has a−C≡Nfunctional group. The name of the compound is composed of a base, which includes the carbon of the−C≡N, suffixed with "nitrile", so for exampleCH3CH2C≡N is called "propionitrile" (or propanenitrile).[1] The prefixcyano- is used interchangeably with the termnitrile in industrial literature. Nitriles are found in many useful compounds, includingmethyl cyanoacrylate, used insuper glue, andnitrile rubber, a nitrile-containingpolymer used inlatex-free laboratory andmedical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known ascyanocarbons.
Inorganic compounds containing the−C≡N group are not called nitriles, butcyanides instead.[2] Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic.
The N−C−C geometry is linear in nitriles, reflecting the sp hybridization of the triply bonded carbon. The C−N distance is short at 1.16 Å, consistent with atriple bond.[3] Nitriles are polar, as indicated by high dipole moments. As liquids, they have highrelative permittivities, often in the 30s.
Around 1832benzonitrile, the nitrile ofbenzoic acid, was prepared byFriedrich Wöhler andJustus von Liebig, but due to minimal yield of the synthesis neither physical nor chemical properties were determined nor a structure suggested. In 1834Théophile-Jules Pelouze synthesizedpropionitrile, suggesting it to be an ether of propionic alcohol and hydrocyanic acid.[7] The synthesis of benzonitrile byHermann Fehling in 1844 by heating ammonium benzoate was the first method yielding enough of the substance for chemical research. Fehling determined the structure by comparing his results to the already known synthesis of hydrogen cyanide by heating ammoniumformate. He coined the name "nitrile" for the newfound substance, which became the name for this group of compounds.[8][9]
In 1903,Arthur Lapworth investigated the formation ofcyanohydrins by addition of hydrocyanic acid toaldehydes andketones and discovered that the actual nucleophile is the cyanide ion, such that the addition of a base increases thereaction rate. This work represented one of the earliest investigations of an organicreaction mechanism.[10][11]
For a long time, nitriles were primarily of academic interest. Between the First andSecond World War, however, research activity increased significantly.[8] By the second half of the 20th century, several large-scale industrial processes had been developed in which nitriles were either produced or utilized. An important example is the development ofpolyamides (polyamide 6.6) in the 1930s, asadiponitrile is a key intermediate in its manufacture and is produced byhydrocyanation ofbutadiene with hydrogen cyanide.[12][13]Acrylonitrile polymers have been known since the 1920s but gained greater importance as synthetic fibers toward the late 1940s.[14]Superglues based oncyanoacrylates have also been available since the late 1940s.[15]
Butyronitrile, according to IUPAC: Butanonitrile (blue marked C atom belongs to the main chain), formally also propanecarbonitrile (blue marked C atom belongs to the substituent)
The functional group of nitriles containing theC≡N triple bond is referred to as the nitrile or cyano group.[16] If the nitrile is the highest-rankingfunctional group, the suffix-nitrile is added to the name of the parent compound. The triply bonded carbon atom is, as always, included in the parent chain.[17] Alternatively, the ending-carbonitrile may be used (analogous to-carboxylic acid), in which case the carbon atom isnot counted as part of the parent chain.[18] This ending must be used if the nitrile group is attached to a ring (as incyclopentanecarbonitrile [wd]) or if not all carbon atoms are part of the parent chain, which is necessarily the case when more than two nitrile groups are present, as these can only be located at the termini of the chain.[19] Due to their relationship to carboxylic acids (the nitrile carbon has the same oxidation state as the carboxyl carbon),trivial names are often derived from the corresponding carboxylic acids using the ending-onitrile (for example,benzoic acid tobenzonitrile).[20] If the nitrile function isnot the principal functional group in the molecule, the prefixcyano- is used together with the appropriatelocant. In this case as well, the triple-bonded carbon atom isnot counted as part of the parent chain.[19]
Compound classes containing aC≡N triple bond. Left (from top to bottom): hydrogen cyanide, nitriles, isonitriles. Center: cyanates, thiocyanates, cyanamides. Right: nitrile oxides, nitrile sulphides, nitrilimines, nitrilium ions
Nitriles are isomeric withisonitriles (isocyanides). These also contain aC≡N triple bond; however, the substituent is bonded via the nitrogen atom, which results in azwitterionic structure.[21]
Compounds in which an oxygen atom is bonded to the carbon atom of aC≡N group are referred to ascyanates.[22]If the oxygen atom is replaced by a sulfur orselenium atom, the compounds are termedthiocyanates orselenocyanates [wd].[23][24]If the cyano group is bonded to a nitrogen atom, the compound is referred to as acyanamide.[25]
In addition to nitriles, other classes of compounds are known that contain aC≡N triple bond in which the nitrogen atom forms a fourth bond and is therefore positively charged. Innitrile oxides, an oxygen atom is additionally bonded to the nitrogen atom.[26]If this atom is sulfur or another nitrogen atom instead, the compounds are referred to asnitrile sulfides [wd] ornitrilimines, respectively.[27][28]If the nitrogen atom of the nitrile is protonated or carries an additional organic substituent, the compound is anitrilium ion.[29]If the nitrogen atom carries an organic substituent bearing a negatively charged carbon atom, the species is anitrile ylide, a subclass ofylides.[30]
Industrially, the main methods for producing nitriles areammoxidation andhydrocyanation. Both routes aregreen in the sense that they do not generate stoichiometric amounts of salts.
In general, metal cyanides combine with alkyl halides to give a mixture of the nitrile and theisonitrile, although appropriate choice ofcounterion andtemperature can minimize the latter. Analkyl sulfate obviates the problem entirely, particularly in nonaqueous conditions (thePelouze synthesis).[5]
In the Kolbe nitrile synthesis (a nucleophilic substitution reaction), an alkanonitrile and an alkali halide are formed from a reactivehalohydrocarbons and an alkali cyanide (sodium cyanide orpotassium cyanide). The reaction is particularly suitable for primary, allylic, and benzylic halides. Secondary alkyl halides provide lower yields, whereas tertiary halides undergo exclusivelyelimination reaction instead of substitution. In addition to halides, substrates bearing other good leaving groups may also be employed. In contrast to alkali cyanides,silver cyanide is unsuitable for nitrile synthesis, as it preferentially formsisonitriles.[31] An example of the Kolbe nitrile synthesis is the reaction ofmethyl iodide with sodium cyanide to yieldacetonitrile andsodium iodide:[32]
Similarly,1,3-dibromopropane reacts with sodium cyanide to formglutaronitrile[33], and1-iodooctane reacts with potassium cyanide to givenonannitrile.[34] Cyanations can also be carried out using hydrogen cyanide in combination withtriethylaluminum or withdiethylaluminum cyanide; for example, in the ring opening of anepoxide to a β-cyanohydrin or in the 1,4-addition of cyanide to anenone.[35][36]Trimethylsilylcyanide is another cyanating reagent capable of opening epoxides to β-cyanohydrins, with concomitant silylation of the oxygen atom.[37] Trimethylsilyl cyanide also enables substitution of tertiary alkyl halides, which is not feasible under Kolbe nitrile synthesis conditions.[31]
In the presence of suitable transition metal catalysts,hydrocyanation allows addition of hydrogen cyanide to the multiple bonds ofalkenes and alkynes to afford nitriles. Nickel catalysts are typically employed. Direct handling of hydrogen cyanide is often unnecessary, as synthetic equivalents such asacetone cyanohydrin orisovaleronitrile may be used.[38] An important industrial process is the hydrocyanation ofbutadiene toadiponitrile.[13]
Production of nitriles (center) by dehydration. Suitable starting materials are carboxylic acid amides (left) or aldoximes (right). The atoms of the eliminated water molecule are highlighted in blue
Specifically,carboxylic acid amides andoximes can be converted to nitriles bydehydration (elimination of water). Numerous reagents and methodologies are available for this transformation.[41][42][43] Methods for nitrile synthesis via dehydration ofnitroalkanes have also been described.[44]
In the production of acrylonitrile, a side product isacetonitrile. On an industrial scale, several derivatives ofbenzonitrile,phthalonitrile, as well as Isobutyronitrile are prepared by ammoxidation. The process is catalysed bymetal oxides and is assumed to proceed via the imine.
Ammoxidation is a heterogeneously catalyzed gas-phase reaction in which aliphatic or methyl-substituted aromatic compounds react with oxygen (air) andammonia to form nitriles, with water as a by-product. Reaction temperatures exceed 300 °C, and oxides ofvanadium,chromium, ormolybdenum serve as catalysts.[86]Acrylonitrile, an important precursor forpolymer production (see Use section), is primarily manufactured by ammoxidation ofpropene.[14] The principal industrial route to hydrogen cyanide is theAndrussov process, i.e., ammoxidation ofmethane over aplatinum catalyst. However, a significant proportion of global hydrogen cyanide production arises as a by-product of acrylonitrile manufacture.[87]
Aromatic nitriles are often prepared in the laboratory from the aniline viadiazonium compounds. This is theSandmeyer reaction. It requires transition metal cyanides.[96]
Synthesis of aromatic nitriles via silylated cyanohydrins
Thecyanohydrins are a special class of nitriles. Classically they result from the addition of alkali metal cyanides to aldehydes in thecyanohydrin reaction. Because of the polarity of the organic carbonyl, this reaction requires no catalyst, unlike the hydrocyanation of alkenes. O-Silyl cyanohydrins are generated by the additiontrimethylsilyl cyanide in the presence of a catalyst (silylcyanation). Cyanohydrins are also prepared by transcyanohydrin reactions starting, for example, withacetone cyanohydrin as a source of HCN.[97]
Production of cyanohydrins: An aldehyde or ketone reacts with an alkali cyanide. M denotes an alkali metal
Usingchiral pool starting materials,enantioselective synthesis enables access to α-chiral nitrile-containing compounds ineutomeric form, such asvildagliptin andsaxagliptin. Conventional transformations can introduce the nitrile functionality; for example, an enantiomerically pure amide or oxime derived from naturally enantiopureproline may be dehydrated. The applicability of such strategies depends on the specific target molecule. Asymmetric cyanation reactions are also established.[104] Of particular importance is the asymmetric hydrocyanation of carbonyl compounds (see section on cyanohydrin preparation). In addition, numerous asymmetric hydrocyanations of imines have been developed, affording enantiomerically pure α-aminonitriles.[102]
Carbocyanation enables addition of a nitrile group across a multiple bond to yield a further nitrile. Aryl nitriles can be added to alkynes under catalysis bybis(cyclooctadiene)nickel(0) andtrimethylphosphine, affording α,β-unsaturated nitriles. Modification of the reaction conditions, for example by employing a differentphosphane or adding aLewis acid-base concept such as trimethylaluminum ortriphenylborane, allows addition of non-aromatic nitriles, both saturated and α,β-unsaturated.[112] Carbocyanation reactions that couple two molecules while introducing a nitrile group are also known, usinghexabutyldistannane andtosyl cyanide as the cyanide source.[113]
Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.
Thehydrolysis of nitriles RCN proceeds in the distinct steps under acid or base treatment to first givecarboxamidesRC(O)NH2 and thencarboxylic acidsRC(O)OH. The hydrolysis of nitriles to carboxylic acids is efficient. In acid or base, the balanced equations are as follows:
RC≡N + 2 H2O + HCl → RC(O)OH + NH4Cl
RC≡N + H2O + NaOH → RC(O)ONa + NH3
Strictly speaking, these reactions are mediated (as opposed tocatalyzed) by acid or base, since one equivalent of the acid or base is consumed to form the ammonium or carboxylate salt, respectively.
Kinetic studies show that the second-order rate constant for hydroxide-ion catalyzed hydrolysis ofacetonitrile toacetamide is 1.6×10−6 M−1 s−1, which is slower than the hydrolysis of the amide to the carboxylate (7.4×10−5 M−1 s−1). Thus, the base hydrolysis route will afford the carboxylate (or the amide contaminated with the carboxylate). On the other hand, the acid catalyzed reactions requires a careful control of the temperature and of the ratio of reagents in order to avoid the formation of polymers, which is promoted by the exothermic character of the hydrolysis.[118] The classical procedure to convert a nitrile to the corresponding primary amide calls for adding the nitrile to cold concentratedsulfuric acid.[119] The further conversion to the carboxylic acid is disfavored by the low temperature and low concentration of water.
RC≡N + H2O → RC(O)NH2
Two families of enzymes catalyze the hydrolysis of nitriles.Nitrilases hydrolyze nitriles to carboxylic acids:
Nitriles are susceptible tohydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.[121] In conventionalorganic reductions, nitrile is reduced by treatment withlithium aluminium hydride to the amine. Reduction to theimine followed by hydrolysis to the aldehyde takes place in theStephen aldehyde synthesis, which usesstannous chloride in acid.
Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to theC≡N group.[122][123] Strong bases are required, such aslithium diisopropylamide andbutyl lithium. The product is referred to as anitrile anion. These carbanions alkylate a wide variety of electrophiles. Key to the exceptional nucleophilicity is the small steric demand of theC≡N unit combined with its inductive stabilization. These features make nitriles ideal for creating new carbon-carbon bonds in sterically demanding environments.
In the so-called Franchimont Reaction (developed by the Belgian doctoral student Antoine Paul Nicolas Franchimont (1844-1919) in 1872), an α-cyanocarboxylic acid heated in acid hydrolyzes anddecarboxylates to a dimer.[128]
More than 100 naturally occurring nitriles were known as early as the 1990s,[137] and several hundred have since been identified.[138] These compounds occur in bacteria, fungi, plants, andarthropods andsponges.[137][138] Thebiosynthesis of naturally occurring nitriles frequently begins with amino acids. TheirN-hydroxylation followed bydecarboxylation (cleavage of the carboxylic acid group as carbon dioxide) yieldsoximes, which serve as the direct precursors of nitriles.[137]
Cyanohydrins and theirglycosides, referred to ascyanogenic glycosides, are widespread in nature and occur in several thousand plant species.[11][138] More than one hundred naturally occurring cyanogenic glycosides have been identified.[138] Plants utilize cyanogenic glycosides for defense and possibly also as areserve substance fornitrogen. They are biosynthesized from a limited number ofamino acids and variouscarbohydrates.[11] Upon tissue damage, the glycosides come into contact withenzymes (Β-glucosidase andhydroxynitrillyase), which first release the aglycone (a cyanohydrin) and subsequently cleave it into a carbonyl compound and toxic hydrocyanic acid.Amygdalin is a glycoside ofmandelonitrile and one of the most widespread cyanogenic glycosides; it occurs particularly in the seeds of therose family (Rosaceae), includingcultivated apple,apricot,peach,plum,cherry, andalmond tree.[161] Whereas amygdalin is confined to the seeds of peaches, other parts of the plant predominantly containprunasin.[162] Prunasin is likewise a glycoside of mandelonitrile; however, its sugar moiety is a monosaccharide (rather than a disaccharide as in amygdalin). In almonds and bitter almonds, prunasin serves as a biosynthetic precursor of amygdalin.[163] Prunasin is also present inlaurel cherry.[164] Prunasin andsambunigrin, along with several other cyanogenic glycosides, occur inpassion flower; inpapaya, prunasin predominates.[165][166] Sambunigrin, also a glycoside of mandelonitrile, is found in several species of the genuselderberry (Sambucus), includingblack elderberry andCanadian elderberry,[167][168] as well as inXimenia americana.[169]Vicianin, another mandelonitrile glycoside, occurs in ferns of the genusDavellia (familyDavalliaceae).[170]Dhurrin is a cyanogenic glycoside of4-hydroxymandelonitrile found insorghum millet and other species of the genussorghum millet, includingSorghum halepense.[171][172]Linamarin (with the aglyconeacetone cyanohydrin) andlotaustralin (with the aglyconebutanone cyanohydrin) occur in the generaLinum (for example incommon flax) andlotus flowers, as well as in thecommon bean.[173] Both compounds are also present in cassava.[174] The mistletoe speciesLoranthus micranthus (genusLoranthus) contains linamarin gallate, a derivative in which linamarin is additionally esterified withgallic acid.[175] Therubber tree also contains linamarin; studies indicate that in this case the compound likely serves as an important storage substance in addition to its defensive function. The seeds contain particularly high concentrations, and during seedling development the compound is metabolized without releasing hydrocyanic acid, suggesting utilization in other biosynthetic pathways.[176]
Peach tree
Structure of amygdalin
Struktur des Prunasins
Mandelonitrile, the aglycone of amygdalin and prunasin
Benzoyl cyanide is found in the defensive secretions of various arthropods
In addition to arthropods, marine animals also contain nitrile compounds. These includebursatellin frombroad-footed snails of the genusBursatella[188] and thecalyculins isolated from sponges.[189] Thealbanitriles from sponges of the genusMycale are linear compounds (chain length 16 to 18 carbon atoms) bearing a nitrile group at one or both termini and several additional C≡C triple bonds.[190]
Nitriles are among the most abundant organic molecules in space, and more than ten distinct compounds have been unequivocally detected.[200] Hydrogen cyanide was one of the first polyatomic species identified in space and occurs there relatively frequently and in substantial quantities.[201] Other nitriles detected in space includeacetonitrile andaminoacetonitrile,[200] as well asbutyronitrile,[202]cyanoacetylene, andcyanopolyins containing two to five conjugated triple bonds.[203] Hydrogen cyanide, cyanoacetylene, anddicyane are present in the atmosphere of Saturn’s moonTitan.[204]
Nitriles may have played a significant role inchemical evolution on Earth.[205][204] Experimental studies have demonstrated that hydrogen cyanide can form under a wide range of plausible prebiotic conditions. Possible starting materials include gas mixtures ofmethane,carbon dioxide, nitrogen,ammonia, and/orhydrogen. Various energy sources, such as electrical discharges orultraviolet radiation, are likewise conceivable. Under simple conditions, hydrogen cyanide can give rise to numerous additional organic molecules.[206] Hydrogen cyanide and other nitriles, such as cyanoacetylene and dicyan, are considered potential precursors ofnucleic bases.[204][206] Aminonitriles, in turn, are regarded as likely precursors of amino acids andpeptides; for example, aminoacetonitrile is a precursor of glycine. An analogous process to the Strecker synthesis is proposed, in which α-aminopropionitrile initially forms from cyanide,acetaldehyde, and ammonia and is subsequently hydrolyzed toalanine.[205][207][208]
Hydrogen cyanide is used on a large scale in the chemical industry as an intermediate for the production of other compounds.Acrylonitrile is an important feedstock for the manufacture of nitrile polymers.Acetonitrile is an important solvent. Other nitriles are employed as fragrances, pesticides, and chemical reagents. The nitrile group also plays a significant role in the development of active pharmaceutical ingredients.
Several widely used polymers containacrylonitrile as a monomer and therefore incorporate nitrile groups. Purepolyacrylonitrile (PAN) is difficult to process; consequently, during its production, 85 to 99% acrylonitrile is almost always copolymerized with small amounts of other monomers.[14]Copolymers containing 35 to 85% acrylonitrile, together with other monomers such asvinyl acetate andmethacrylic acid methyl ester, are also employed.[14][213] Nitrile polymers are among the most important fully synthetic materials for textile fibers, alongsidepolyesters andpolyamidess.[14][214] These fibers, known asacrylic fibers, are produced on the scale of several million tons per year. In 2000, global production was approximately 2.7 million tons.[14][215] Acrylic fibers are used in garments (such as socks and sweaters), blankets, carpets, and knitting yarn, among other applications.[14][216] PAN is also the principal precursor for the production ofcarbon fiber, which is used as an exceptionally lightweight yet strong material in automotive and aircraft construction.[14][213][217][218] Global production of the monomer acrylonitrile was approximately 3.2 million tons in 1988.[87]
Acrylonitrile butadiene rubbers are known as nitrile rubbers and exhibit advantageous properties such as hightensile strength, highabrasion resistance, and resistance to hydrocarbons (oils and fuels). They are therefore used for sealing rings and for oil and fuel hoses.[14] Another important application of nitrile rubber isprotective gloves, which are frequently used in healthcare instead oflatex clothing gloves, as the latter often causelatex allergys.[219] Such gloves are also commonly used when handling hazardous chemicals, including organic solvents.[220]
Another important polymer is theterpolymer of acrylonitrile, butadiene, and styrene (acrylonitrile-butadiene-styrene copolymer). This material is widely used for the outer housings of electronic devices (computers, monitors, and keyboards).[221] Other applications include automotive plastic components (e.g., headlight and mirror housings), refrigerator liners, housings for kitchen appliances, vacuum cleaners, and power tools, as well as suitcases, snack containers,[222] and toys, includingLego.[223][224] ABS is also produced on the scale of several million tons annually; for example, about 2.7 million tons were manufactured in 1992.[222]
Acetonitrile is used as a solvent, particularly in the pharmaceutical industry.[228] According to a market analysis, approximately 180,000 tons of acetonitrile were produced worldwide in 2022, of which around 70% was consumed by the pharmaceutical sector.[229] It is also one of the most important solvents for analyses performed byhigh-performance liquid chromatography.[228][230] The thermal decomposition ofazobisisobutyronitrile (AIBN) and related compounds (e.g.,azobiscyclohexanecarbonitrile) generates relatively stable radicals; accordingly, these compounds are used asradical initiators in radical reactions, particularly polymerizations.[231] The quinoneDDQ, which contains two nitrile groups, is a widely used oxidizing agent, including in pharmaceutical synthesis.[232] Nitrile groups can be incorporated into biomolecules as probes for infrared spectroscopic investigations.[233] Some nitriles serve as starting materials for the synthesis of pharmaceuticals.[234]Ketoprofen is ananti-inflammatory agent approved in some EU countries;propionitrile is used in its industrial synthesis.[235][236]
Nitriles occur in numerous classes of drugs. Between 2010 and 2020, at least one drug containing a nitrile function was approved annually by the USFood and Drug Administration. The nitrile group exhibits characteristic physicochemical properties that are important indrug design. Structurally, it has a linear geometry and occupies very little space—approximately one eighth of the volume of amethyl group. As a ligand substituent, it is therefore well suited to occupying narrow and deep cavities within thebinding site of a target protein that are otherwise difficult to access. Incorporation of a nitrile group into a molecule generally reduces itsoctanol-water partition coefficient or increases its aqueous solubility. This often favorably influencesbioavailability,plasma half-life, and thus the duration of action oflipophilic compounds. In medicinal products, the nitrile group is typically metabolically stable.[237] The nitrile group isisosteric with thecarbonyl group, thehydroxy group, and the chlorine atom. It therefore exhibits similar electronic and steric properties and can be exchanged with these groups to fine-tune molecular characteristics.[238]
In certain cases, nitrile groups exert their effect primarily through steric interactions (i.e., spatial complementarity) by formingvan der Waals forces with amino acid residues. This applies to thetyrosine kinase inhibitorbosutinib, which is used inchronic myeloid leukemia.Crystal structures have been reported in which bosutinib is complexed with various tyrosine kinases. Inhibitors ofreverse transcriptase, such asEtravirin andRilpivirin, are used in combination therapies againstHIV. The acrylonitrile substructure of rilpivirine penetrates an aromatic cage composed oftyrosine,phenylalanine, andtryptophan, as demonstrated by the corresponding three-dimensional structure published in 2008.[251] Theserotonin reuptake inhibitorcitalopram, used in the treatment of depression, was the most frequently prescribed psychotropic drug in Germany in 2016, with 290 million defined daily doses. The nitrile group ofescitalopram exhibits optimal complementarity to both the central and an additional allosteric binding site of the transporter protein, as evidenced by crystal structure analysis.[252]
Over 30 nitrile-containing pharmaceuticals are currently marketed for a diverse variety of medicinal indications with more than 20 additional nitrile-containing leads in clinical development. The types of pharmaceuticals containing nitriles are diverse, fromvildagliptin, an antidiabetic drug, toanastrozole, which is the gold standard in treating breast cancer. In many instances the nitrile mimics functionality present in substrates for enzymes, whereas in other cases the nitrile increases water solubility or decreases susceptibility to oxidative metabolism in the liver.[253] The nitrile functional group is found in several drugs.
A few dozen nitriles are used as fragrance ingredients in cosmetics. These includecinnamic acid nitrile,dodecanitrile,benzonitrile, andgeranyl nitrile.[254][255][256] Some nitriles possess fragrances similar to those of the correspondingaldehydes but are considerably more stable, making them suitable substitutes. For example, geranyl nitrile provides a citrus note and, unlike the structurally analogouscitral, is resistant to oxidation.[257]
Various nitriles are employed as pesticides. Cyano groups are present in certainpyrethroids. Pyrethroids are carboxylic acid esters; by using3-phenoxymandelonitrile as the alcohol component, as indeltamethrin andcypermethrin, a class of particularly potent derivatives has been developed.[258]Azoxystrobin became the world’s best-selling agricultural fungicide in 1999, only a few years after its introduction, with sales exceeding 400 million US dollars, and it has retained its market significance for more than 15 years, remaining the leading fungicide in 2016.[259][260] Azoxystrobin was developed on the basis of the naturally occurringstrobilurin. Key structural modifications relative to the parent compound include replacement of double bonds with aromatic rings and introduction of a cyano group onto the pre-existing ring system.[260] A widely used nitrile-containing insecticide isfipronil.[261]
cyanoacrylates are used asadhesives because, as single-component formulations, they cure rapidly under ambient conditions and can bond a wide range of materials. By far the most widely used compound in this field is2-cyanoacrylic acid ethyl ester, while2-cyanoacrylic acid methyl ester andallyl cyanoacrylate are used to a lesser extent.[262] Cyanoacrylate adhesives are also applied in medicine for wound closure as an alternative to suturing. However, short-chain alkyl esters (e.g., methyl cyanoacrylate) frequently cause adverse effects, particularlyinflammation; therefore, different compounds are employed in medical applications than in technical uses. In particular,butyl cyanoacrylate and2-octyl cyanoacrylate are predominantly used.[15]
Nitriles are used aselectrolyte additives inlithium batterys. For example, the addition of1,3,6-hexanetricarbonitrile leads to a significant performance improvement compared with a corresponding battery without such an additive. The mechanism of action of nitrile additives has not yet been fully elucidated.[263][264]
Carl W. Scheele (1782)"Försök, beträffande det färgande ämnet uti Berlinerblå" (Experiment concerning the colored substance in Berlin blue),Kungliga Svenska Vetenskapsakademiens handlingar (Royal Swedish Academy of Science's Proceedings), 3: 264–275 (in Swedish).
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