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The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
Nitrilase was first discovered in the early 1960s for its ability to catalyze the hydration of a nitrile to a carboxylic acid. [2] Although it was known at the time that nitrilase could operate with wide substrate specificity in producing the corresponding acid, later studies reported the first NHase (nitrile hydratase) activity exhibited by nitrilase.
The mechanism for the reduction of a nitrile to an aldehyde with DIBAL-H. The hydride reagent Diisobutylaluminium hydride, or DIBAL-H, is commonly used to convert nitriles to the aldehyde. [14] Regarding the proposed mechanism, DIBAL forms a Lewis acid-base adduct with the nitrile by formation of an N-Al bond. The hydride is then transferred to ...
Nitrile hydratase and amidase are two hydrating and hydrolytic enzymes responsible for the sequential metabolism of nitriles in bacteria that are capable of utilising nitriles as their sole source of nitrogen and carbon, and in concert act as an alternative to nitrilase activity, which performs nitrile hydrolysis without formation of an intermediate primary amide.
For example: an electron-poor nitrile is a good electrophile (readily susceptible to attack from alkoxides etc.) but a poor nucleophile would typically be easier to protonate than to participate in the reaction and hence would be expected to react more readily under basic rather than acidic conditions.
With nitrile electrophiles, nucleophilic addition take place by: [1] hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction.
Nitriles are only weakly basic [2] and are poor nucleophiles, but they will attack very reactive electrophiles such as carbocations. [3] Nitrilium salts can be prepared by reacting nitriles with trialkyloxonium salts. The nitrilium ions thus formed can then be reduced to secondary amines with sodium borohydride in diglyme.
In enzymology, an aliphatic nitrilase also known as aliphatic nitrile aminohydrolase (EC 3.5.5.7) is an enzyme that catalyzes the hydrolysis of nitriles to carboxylic acids: R-CN + 2 H 2 O ⇌ {\displaystyle \rightleftharpoons } R-COOH + NH 3