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Concept
Hydrogen cyanide
Summary
Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structural formula . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature.
Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. The tautomer of HCN is HNC, hydrogen isocyanide.
Hydrogen cyanide is weakly acidic with a pKa of 9.2. It partially ionizes in water solution to give the cyanide anion, CN−. A solution of hydrogen cyanide in water, represented as HCN, is called hydrocyanic acid. The salts of the cyanide anion are known as cyanides.
HCN has a faint bitter almond–like odor that some people are unable to detect owing to a recessive genetic trait. The volatile compound has been used as inhalation rodenticide and human poison, as well as for killing whales. Cyanide ions interfere with iron-containing respiratory enzymes.
Hydrogen cyanide will react with alkenes under catalysis of nickel complexes. This reaction is called hydrocyanation.
RCH=CH2 + HCN → RCH2-CH2-CN
Four molecules of HCN will tetramerize into diaminomaleonitrile, which can be converted to various purines.
Hydrogen cyanide was first isolated from a blue pigment (Prussian blue) which had been known since 1706, but whose structure was unknown. It is now known to be a coordination polymer with a complex structure and an empirical formula of hydrated ferric ferrocyanide. In 1752, the French chemist Pierre Macquer made the important step of showing that Prussian blue could be converted to an iron oxide plus a volatile component and that these could be used to reconstitute it. The new component was what is now known as hydrogen cyanide.
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