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Ammonium cyanide

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Ammonium cyanide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CN.H3N/c1-2;/h;1H3/q-1;/p+1 checkY
    Key: ICAIHGOJRDCMHE-UHFFFAOYSA-O checkY
  • InChI=1/CN.H3N/c1-2;/h;1H3/q-1;/p+1
    Key: ICAIHGOJRDCMHE-IKLDFBCSAW
  • [C-]#N.[NH4+]
Properties
NH4CN
Molar mass 44.0559 g/mol
Appearance colourless crystalline solid
Density 1.02 g/cm3
Melting point 36 °C (decomp.)
very soluble
Solubility very soluble in alcohol
Structure
cubic
Related compounds
Other anions
Ammonium hydroxide
Ammonium azide
Ammonium nitrate
Other cations
Sodium cyanide
Potassium cyanide
Related compounds
Ammonia
Hydrogen cyanide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ammonium cyanide is an unstable inorganic compound with the formula NH4CN.

Uses

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Ammonium cyanide is generally used in organic synthesis.[citation needed] Being unstable, it is not shipped or sold commercially.

Preparation

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Ammonium cyanide is prepared by combining solutions of hydrogen cyanide and ammonia:[citation needed]

HCN + NH3 → NH4CN

It may be prepared by the reaction of calcium cyanide and ammonium carbonate:[citation needed]

Ca(CN)2 + (NH4)2CO3 → 2 NH4CN + CaCO3

In dry state, ammonium cyanide is made by heating a mixture of potassium cyanide or potassium ferrocyanide with ammonium chloride and condensing the vapours into ammonium cyanide crystals:[citation needed]

KCN + NH4Cl → NH4CN + KCl

Reactions

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Ammonium cyanide decomposes to ammonia and hydrogen cyanide, often forming a black polymer of hydrogen cyanide:[1]

NH4CN → NH3 + HCN

It undergoes salt metathesis reaction in solution with a number of metal salts to form metal–cyanide complexes.

Reaction with ketones and aldehydes yield aminonitriles, as in the first step of the Strecker amino acid synthesis:

NH4CN + CH3COCH3 → (CH3)2C(NH2)CN + H2O

Toxicity

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Ammonium cyanide is highly toxic.

Notes

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  1. ^ Matthews, Clifford N (1991). "Hydrogen cyanide polymerization: A preferred cosmochemical pathway". Bioastronomy: The Search for Extraterrestrial Life—The Exploration Broadens. Lecture Notes in Physics. Vol. 390. pp. 85–87. doi:10.1007/3-540-54752-5_195. ISBN 978-3-540-54752-5.

References

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  • A. F. Wells, Structural Inorganic Chemistry, 5th ed., Oxford University Press, Oxford, UK, 1984.