Nitriles: Structure, Formula, Properties & Uses

Nitriles, often known as Cyano Compounds in organic chemistry, are organic compounds. The cyano group, which is represented as (−C≡N) and is connected to the carbon atom, is a functional group in these organic compounds. Nitriles can also be considered organic cyanides, although they are often less harmful than simple cyanide salts like sodium cyanide or potassium cyanide (NaCN or KCN). As indicated by high dipole moments, Nitriles are polar in nature. 

Key Terms: Nitrile, Hydrolysis, Reduction of Nitriles, Cyano Compounds, Organic Compounds, Cyanides, Electronegativity, Molecules

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What are Nitriles?

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A nitrile is a group of chemical compounds that contain an organic hydrocyanic acid derivative. All organic compounds having the generic formula R−C≡N are included in this category. Because of its oil resistance, nitrile is commonly utilized for making acrylonitrile copolymers, which are used in gloves, gaskets, seals, and tubing. Nitrile also protects the materials it encloses against corrosion.

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Structure and Formula of Nitrile

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The structure of Nitrile is as follows:

Nitrile is an organic compound that contains the Cyano functional subunit or group. The CN- structure of nitrile is formed via triple bonding between nitrogen and carbon atoms. R -C ≡ N is the general nitrile formula, where R denotes the organic component or group.

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Physical and Chemical Properties of Nitrile

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Nitriles have chemical and physical characteristics. The properties of nitriles are given as follows:

• Nitriles have boiling points ranging from 82 to 118 degrees Celsius.
• They resemble colourless liquids and solids with distinct odours.
• Nitriles are polar and have a high electronegativity.
• They also have significant dipole-to-dipole shifts.
• Even the Van der Waals dispersion forces between molecules are visible in nitriles.
• Nitriles are water-soluble, however, their water solubility diminishes as the chain length increases.

Acids, oils, and chemicals can readily degrade vinyl and latex gloves when it comes to the melting point of nitrile. However, nitriles still have a stronger tolerance to such chemicals. In comparison to latex gloves, they can also withstand higher temperature ranges. Nitrile has the ability to withstand temperatures ranging from -40 to +180 degrees Celsius.

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Reactions of Nitriles

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When exposed to particular reactants or circumstances, nitrile groups in organic compounds can undergo a variety of reactions. A nitrile group can be hydrolyzed, reduced, or expelled from a molecule as a cyanide ion.

Hydrolysis of Nitriles

The hydrolysis of nitriles to create carboxylic acids is one of the most effective processes involving nitriles. The mechanism of this reaction differs slightly depending on whether the fluid is acidic or basic. The nitrile is protonated when acid catalysis is used. Protonation boosts the nitrile's electrophilicity, allowing it to take water, a weak nucleophile. The strong nucleophilic hydroxide anion can directly contribute to the carbon-nitrogen triple bond when hydrolysis is catalyzed by a base. Both methods produce an amide intermediate. 

Hydrolysis of Nitriles

Reduction of Nitriles

Lithium aluminium hydride is used to reduce nitriles to primary and tertiary amines. Some catalysts are present during the reduction process. For the production of primary amines, reducing nitriles using lithium aluminium hydride LiAlH₄ is a great technique. Two nucleophilic additions of a hydride to the electrophilic carbon in the nitrile produce this reaction. The main amine is formed by further protonation with an aqueous work-up.

Reduction of Nitriles

Alkylation of Nitriles

Nitrile anions are formed due to the alkylation of nitrile compounds.

Alkylation of Nitriles

Some of the other reactions are Friedel–Crafts acylation,  nucleophilic addition reactions, etc.

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Uses of Nitriles

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Nitriles are employed in a variety of industrial and medical settings. The following are some of the several Nitrile applications:

• The various nitrile compounds can be used as anti-diabetic medications. These medications are effective in the treatment of breast cancer.
• Nitriles can also be used to make nitrile seals, gloves, and hoses. This is due to nitriles' strong resistance to a wide range of chemicals.
• Pericyazine, a nitrile compound, is utilized in the treatment of opiate addiction as an antipsychotic. This nitrile compound can be found in a variety of animals and plants.
• Nitriles are also suitable for use in a variety of oil-resistant elements.
• They're ideal for scenarios and settings where work must be done in frigid conditions.
• Hydraulic hoses, aeronautical systems, and automotive systems all use nitriles.

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Things to Remember

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• A nitrile is an organic molecule that contains a −C ≡ N functional group. 
• Nitriles can be found in a variety of products, including super glue and nitrile rubber, a nitrile-containing polymer used in the latex-free laboratory and medical gloves.
• Under acid or base treatment, nitriles are hydrolyzed in two phases, yielding first carboxamides RC(=O)NH₂ and thereafter carboxylic acids RCOOH. 
• Nitriles are efficiently hydrolyzed to carboxylic acids. 
• In typical organic reductions, nitrile is reduced to the amine by treating it with lithium aluminium hydride. 
• Nitriles can be found in a wide range of plants and animals. From terrestrial and marine sources, over 120 naturally occurring nitriles have been isolated. 

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