Nitrile
A nitrile is any
organic compound which has a -
C=
N functional group. The -C=N 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.
Encyclopedia
A
nitrile is any
organic compound which has a -
C=N functional group. The -C
=N 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.
Synthesis of nitriles
Nitriles can be prepared in organic synthesis by the following methods:
...
s
- dehydration of secondary amide
...
s
[i]
[i]
...
s with
triethylamine/
sulfur dioxide,
zeolites, or
sulfuryl chloride...
with
hydroxylamine and
sodium sulfate.
- In one study 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.
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.
- In hydrolysis the nitrile is reacted with an acid and water at a high temperature, or with a base and water. The acid hydrolysis forms a carboxylic acid, the alkali hydrolysis forms a carboxylate.
- In organic reduction the nitrile is reduced by reacting it with hydrogen
| Triple point [i] || 13.8033 K, 7.042 kPa
...
with a
nickel catalyst; an
amine is formed in this reaction.
See also
- For the polymer used to make safety gloves, see Nitrile rubber.
External links
References
- One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate and sodium bicarbonate in dry media under microwave irradiation Sharwan K, Dewan, Ravinder Singh, and Anil Kumar Arkivoc 2006 41-44
- The reductive decyanation reaction: chemical methods and synthetic applications Jean-Marc Mattalia, Caroline Marchi-Delapierre, Hassan Hazimeh, and Michel Chanon Arkivoc pp 90-118 2006
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