Definition

Noun: 1. A type of organic compound: A nitrile is any of a class of organic chemical compounds characterized by the presence of a cyano functional group (-C≡N). This group consists of a carbon atom triple-bonded to a nitrogen atom. Nitriles are often noted for their strong, sometimes unpleasant odors.

Usage and Examples

• Basic Usage:
  • Acrylonitrile is an important nitrile used in the manufacture of plastics and synthetic rubber.
  • The chemist synthesized a new nitrile in the laboratory.
• In Chemical Contexts:
  • The compound was identified as a nitrile due to the characteristic infrared absorption of its cyano group.
  • Some nitriles occur naturally, such as in certain seeds and plants.

Advanced Usage and Notes

• Nomenclature: In systematic chemical naming (IUPAC), nitriles are often named by adding the suffix "-nitrile" to the name of the parent hydrocarbon chain (e.g., "ethanenitrile" for CH₃CN). The common name is frequently derived from the corresponding carboxylic acid (e.g., "acetonitrile" from acetic acid).
• Relation to Other Groups: The -CN group in a nitrile is called the cyano group. When this group is attached to a metal atom, it forms a cyanide complex (e.g., potassium cyanide, KCN), which is an inorganic salt and distinct from organic nitriles, though they share the same CN⁻ ion precursor.

Variants and Related Words

• Cyanide (noun): An inorganic salt or ester of hydrocyanic acid, containing the anion CN⁻ or the -CN group in a different bonding context. Warning: Many cyanides are highly toxic.
• Cyano- (prefix): A combining form used in chemical names to indicate the presence of the -C≡N group, as in "cyanogen" (N≡C-C≡N).
• Nitrile rubber (noun): A synthetic copolymer rubber derived from acrylonitrile and butadiene, known for its resistance to oils and fuels.

Synonyms

• Cyanide (in specific, often older or industrial contexts, though this can be chemically imprecise).
• Alkyl cyanide (a more descriptive synonym, specifying the organic nature).

Related Phrases and Concepts

• Hydrolysis of a nitrile: A chemical reaction where a nitrile reacts with water, typically under acidic or basic conditions, to yield first an amide and then a carboxylic acid.
  • The hydrolysis of the nitrile produced benzoic acid.
• Nitrile synthesis: Refers to various chemical methods for preparing nitriles, such as the dehydration of amides or the reaction of alkyl halides with cyanide salts.

Noun

1. any of a class of organic compounds containing the cyano radical -CN