organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, an acyl cyanide is a

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

and

structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...

. It consists of an

acyl group In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group ( ...

() attached to

cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...

(). Examples include acetyl cyanide, formyl cyanide, and oxalyl dicyanide. Acyl cyanides are reagents in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Synthesis

Classically acyl cyanides are produced by the

salt metathesis A salt metathesis reaction (also called a double displacement reaction, double replacement reaction, or double decomposition) is a type of chemical reaction in which two ionic compounds in aqueous solution exchange their component ions to form two ...

reaction of

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

s with

sodium cyanide Sodium cyanide is a compound with the formula Na C N and the structure . It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also expl ...

: :

\ce  +  \ce \longrightarrow   +  \ce

Alternatively, they can be produced by

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

of acyl

aldoxime In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted ...

s: :

\ce\ce \longrightarrow   +  \ce

Acetyl cyanide is also prepared by

hydrocyanation In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst if the substrate alkene is unactivated. This conversion is conducted on an in ...

ketene In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary valence (chemistry), monovalent functional group, chemical groups (or two separate Substituent, substitution sites in the same molecule). The na ...

: :

\ce +  \ce  \longrightarrow \ce

Reactions

They are mild acylating agents. With aqueous base, acyl cyanides break down to cyanide and the

carboxylate In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an anion, an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,... ...

: :

+  \ce \longrightarrow  \ce  +  \ce  +  \ce

With

azides In chemistry, azide (, ) is a Linear molecular geometry, linear, polyatomic anion with the Chemical formula, formula and Chemical structure, structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the ...

, acyl cyanides undergo the

click reaction Click chemistry is an approach to chemical synthesis that emphasizes efficiency, simplicity, selectivity, and modularity in chemical processes used to join molecular building blocks. It includes both the development and use of "click reactions", a ...

to give acyl

tetrazole A tetrazole is a chemical synthesis, synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atoms and one carbon atom. The name tetrazole also refers to the parent compound - a whitish crystalline powder with the f ...

s.{{cite journal , doi=10.1002/1521-3773(20020617)41:12<2113::AID-ANIE2113>3.0.CO;2-Q, title=A Click Chemistry Approach to Tetrazoles by Huisgen 1,3-Dipolar Cycloaddition: Synthesis of 5-Acyltetrazoles from Azides and Acyl Cyanides, year=2002, last1=Demko, first1=Zachary P., last2=Sharpless, first2=K. Barry, journal=Angewandte Chemie International Edition, volume=41, issue=12, pages=2113–2116, pmid=19746613

References

Functional groups Organic compounds *