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The conversion of a general nitrile to either an amide or carboxylic acid is facilitated by nitrilase. [5] [1] Below is a list of steps involved in transforming a generic nitrile compound with nitrilase: [4] The electrophilic carbon of the nitrile is subject to nucleophilic attack by one of the two SH groups on nitrilase.
The Ritter reaction (sometimes called the Ritter amidation) is a chemical reaction that transforms a nitrile into an N-alkyl amide using various electrophilic alkylating reagents. The original reaction formed the alkylating agent using an alkene in the presence of a strong acid. [1] [2] [3] [4]
The classical procedure to convert a nitrile to the corresponding primary amide calls for adding the nitrile to cold concentrated sulfuric acid. [29] The further conversion to the carboxylic acid is disfavored by the low temperature and low concentration of water. RC≡N + H 2 O → RC(O)NH 2. Two families of enzymes catalyze the hydrolysis of ...
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.
Mechanism for acid-mediated hydrolysis of an amide. [11] ... Secondary amides via an addition reaction between a nitrile and a carbonium ion in the presence of ...
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.
Mechanism for acid-catalyzed hydrolysis of an amide. Upon hydrolysis, an amide converts into a carboxylic acid and an amine or ammonia (which in the presence of acid are immediately converted to ammonium salts). One of the two oxygen groups on the carboxylic acid are derived from a water molecule and the amine (or ammonia) gains the hydrogen ion.
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