Nitrile is an organic compounds containing cyano group (-C》N, containing
trivalent nitrogen) which is attached to one carbon atom with the general
formula RC》N. Their names are corresponding to carboxylic acids by changing '-ic
acid' to the suffix, '-onitrile' which denotes only the 》N atom (triply bound)
excluding the carbon atom attached to it, or the suffix, '-carbonitrile' where
the carbon atom in the -CN is included, whichever preserves a single letter O.
Examples are acetonitrile from acetic acid and benzonitrile from benzoic acid.
The prefix, 'cyano-' is used as an alternative naming system to indicate the
presence of a nitrile group in a molecule for the compounds of salts and
organic derivatives of hydrogen cyanide (HC》N). Isocyanides are salts and hydrocarbyl
derivatives from the isomer, HN+》C-.
Sodium cyanide, NaCN; potassium
cyanide, KCN; calcium cyanide, Ca(CN)2; and hydrocyanic (or prussic) acid, HCN
are examples. Chemically, the simple inorganic cyanides resemble chlorides in
many ways. Organic nitriles act as solvents and are reacted further for various application including;
·
Extraction solvent for fatty acids,
oils and unsaturated hydrocarbons · Solvent for spinning and casting and
extractive distillation based on its selective miscibility with organic
compounds. · Removing agent of colouring matters and aromatic
alcohols · Non-aqueous solvent for titrations and for inorganic
salts · Recrystallization of steroids ·
Parent compound for organic
synthesis · Solvent or chemical intermediate in biochemistry ( pesticide
sequencing and DNA synthesis) ·
High-pressure liquid chromatographic
analysis · Catalyst and component of transition-metal complex
catalysts · Stabilizer for chlorinated
solvents · Chemical intermediate and solvent for perfumes and
pharmaceuticals
Although nitriles don't have a carbonyl group, they are often considered as
derivatives of carboxylic acids. Nitrile undergoes acid hydrolysis to form a
carboxylic acid. Nitrile is reduced to form amine in the presence of nickel
catalyst. Grignard reagents add to nitriles, forming a relatively stable imino
derivative which can be hydrolyzed to a ketone. Metaloimine is hydrolyzed to
give beta-ketoester. Nitrile undergoes a sequence of nucleophilic additions with
an alcohol under acid catalysis, called nitrile alcoholysis. Nitriles are
hydrolyzed to carboxylic acids, alcoholyzed to esters, reduced to amines,
cyclyzed to pyridine derivatives. |