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Hydrogen cyanide
Hydrogen cyanide (also called prussic acid) is a chemical compound with the formula HCN and structural formula H−C≡N. It is a highly toxic and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). 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. A solution of hydrogen cyanide in water, represented as HCN(aq), is called hydrocyanic acid. The salts of the cyanide anion are known as cyanides.
Whether hydrogen cyanide is an organic compound or not is a topic of debate among chemists. It is traditionally considered inorganic, but can also be considered a nitrile, giving rise to its alternative names of methanenitrile and formonitrile.
Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. The isomer of HCN is HNC, hydrogen isocyanide.
About half of people are unable to detect the odor of hydrogen cyanide owing to a recessive genetic trait. For those that can detect it, the odor has been described as bitter almond-like.
Hydrogen cyanide is weakly acidic with a pKa of 9.2. It partially ionizes in water to give the cyanide anion, CN−. HCN forms hydrogen bonds with its conjugate base, species such as (CN−)(HCN)n.
Hydrogen cyanide reacts with alkenes to give nitriles. The conversion, which is called hydrocyanation, employs nickel complexes as catalysts.
Four molecules of HCN will tetramerize into diaminomaleonitrile.
Metal cyanides are typically prepared by salt metathesis from alkali metal cyanide salts, but mercuric cyanide is formed from aqueous hydrogen cyanide:
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Hydrogen cyanide
Hydrogen cyanide (also called prussic acid) is a chemical compound with the formula HCN and structural formula H−C≡N. It is a highly toxic and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). 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. A solution of hydrogen cyanide in water, represented as HCN(aq), is called hydrocyanic acid. The salts of the cyanide anion are known as cyanides.
Whether hydrogen cyanide is an organic compound or not is a topic of debate among chemists. It is traditionally considered inorganic, but can also be considered a nitrile, giving rise to its alternative names of methanenitrile and formonitrile.
Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. The isomer of HCN is HNC, hydrogen isocyanide.
About half of people are unable to detect the odor of hydrogen cyanide owing to a recessive genetic trait. For those that can detect it, the odor has been described as bitter almond-like.
Hydrogen cyanide is weakly acidic with a pKa of 9.2. It partially ionizes in water to give the cyanide anion, CN−. HCN forms hydrogen bonds with its conjugate base, species such as (CN−)(HCN)n.
Hydrogen cyanide reacts with alkenes to give nitriles. The conversion, which is called hydrocyanation, employs nickel complexes as catalysts.
Four molecules of HCN will tetramerize into diaminomaleonitrile.
Metal cyanides are typically prepared by salt metathesis from alkali metal cyanide salts, but mercuric cyanide is formed from aqueous hydrogen cyanide: