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The structure of the nitrile group

A nitrile is any organic compound which has a -CN functional group. The -CN functional group is called a nitrile group. In the -CN group, the carbon atom and the nitrogen atom are triple bonded together. The prefix cyano is used in chemical nomenclature to indicate the presence of a nitrile group in a molecule. A cyanide ion is a negative ion with the formula CN. The -CN group is sometimes, less properly, referred to as a cyanide group or cyano group and compounds with them are sometimes referred to as cyanides.

Nitriles sometimes release the highly toxic CN cyanide ion. See the article on cyanide for a discussion of biological effects and toxicity.


Hydrogen cyanide was first synthesized by K.W. Scheele in 1782 and he was killed in an attempt to get the anhydrous compound [1]. J. L. Gay-Lussac was the first to prepare the pure acid in 1811 and Friedrich Wohler and Justus von Liebig were the first to prepare the first nitriles benzoyl cyanide and benzonitrile in 1832. Théophile-Jules Pelouze synthesized propionitrile in 1834.

Synthesis of nitriles

Nitriles can be prepared in organic synthesis by the following methods:

Amide dehydration
Two intermediates in this reaction are amide tautomer A and its phosphate adduct B.
one-pot synthesis from aldehyde
In one study [3] an aromatic or aliphatic aldehyde is reacted with hydroxylamine and anhydrous sodium sulfate in a dry media reaction for a very small amount of time under microwave irradiation through an intermediate aldoxime.
In the so-called Franchimont Reaction (A. P. N. Franchimont, 1872) an α-bromocarboxylic acid is dimerized after hydrolysis of the cyanogroup and decarboxylation [7]

Reactions of nitriles

Nitrile groups in organic compounds can undergo various reactions when subject to certain reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.

Carbocyanation Nakao 2007

See also

External links


  1. David T. Mowry (1948). "The Preparation of Nitriles". Chem. Rev. 42 (2): 189–283. doi:10.1021/cr60132a001.
  2. Chun-Wei Kuo, Jia-Liang Zhu, Jen-Dar Wu, Cheng-Ming Chu, Ching-Fa Yao and Kak-Shan Shia (2007). "A convenient new procedure for converting primary amides into nitriles". Chem. Commun. 2007: 301–303. doi:10.1039/b614061k.
  3. Sharwan K, Dewan, Ravinder Singh, and Anil Kumar (2006). "One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate (anhyd) and sodium bicarbonate in dry media under microwave irradiation" (open access). Arkivoc: (ii) 41-44.
  4. Template:OrgSynth
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  6. Reynold C. Fuson, Oscar R. Kreimeier, and Gilbert L. Nimmo (1930). "RING CLOSURES IN THE CYCLOBUTANE SERIES. II. CYCLIZATION OF α,α′-DIBROMO-ADIPIC ESTERS". J. Am. Chem. Soc. 52 (10): 4074–4076. doi:10.1021/ja01373a046.
  8. Smith, Andri L.; Tan, Paula (2006). "Creatine Synthesis: An Undergraduate Organic Chemistry Laboratory Experiment". J. Chem. Educ. 83: 1654.
  9. The reductive decyanation reaction: chemical methods and synthetic applications Jean-Marc Mattalia, Caroline Marchi-Delapierre, Hassan Hazimeh, and Michel Chanon Arkivoc (AL-1755FR) pp 90-118 2006 Article
  10. Yoshiaki Nakao, Akira Yada, Shiro Ebata, and Tamejiro Hiyama (2007). "A Dramatic Effect of Lewis-Acid Catalysts on Nickel-Catalyzed Carbocyanation of Alkynes". J. Am. Chem. Soc. (Communication)|format= requires |url= (help). 129 (9): 2428–2429. doi:10.1021/ja067364x.

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