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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. [3] [4] That is, amide compounds could also be formed via nitrile hydrolysis. Further research has revealed several ...
The resulting nitrilium ion is hydrolyzed to the desired amide. Primary, [7] secondary, [4] tertiary, [8] and benzylic [9] alcohols, [1] as well as tert-butyl acetate, [10] also successfully react with nitriles in the presence of strong acids to form amides via the Ritter reaction. A wide range of nitriles can be used.
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.
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 ...
The imidium chloride salts is thermodynamically unstable, and low temperatures help prevent elimination to an amide and alkyl chloride. [8] It should be appreciated that the Pinner reaction refers specifically to an acid catalyzed process, but that similar results can often be achieved using base catalysis.
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 ...
Cationic nitrile complexes are however susceptible to nucleophilic attack at carbon. Consequently some nitrile complexes catalyze the hydrolysis of nitriles to give the amides. [7] Fe- and Co-nitrile complexes are intermediates in nitrile hydratase enzymes. N-coordination activates the sp-hybridized carbon center toward attack by nucleophiles ...
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.