Ammonium cyanide

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Ammonium cyanide
Ammonium cyanide.png
Ammonium-cyanide-3D-vdW.png
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/CN.H3N/c1-2;/h;1H3/q-1;/p+1 Yes check.svgY
    Key: ICAIHGOJRDCMHE-UHFFFAOYSA-O Yes check.svgY
  • 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
Appearancecolourless crystalline solid
Density 1.02 g/cm3
Boiling point 36 °C (97 °F; 309 K)
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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Infobox references

Ammonium cyanide is an unstable inorganic compound with the formula NH4CN.

Contents

Uses

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

Preparation

Ammonium cyanide is prepared in solution by bubbling hydrogen cyanide into aqueous ammonia at a low temperature

HCN + NH3 (aq) → NH4CN (aq)

It may be prepared by the reaction of calcium cyanide and ammonium carbonate:

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:

KCN + NH4Cl → NH4CN + KCl

Reactions

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

The solid or its solution is highly toxic. Ingestion can cause death. Exposure to the solid can be harmful as it decomposes to highly toxic hydrogen cyanide and ammonia.

Chemical analysis

Ammonium cyanide may be analyzed by heating the salt and trapping the decomposed products: hydrogen cyanide and ammonia in water at low temperatures. The aqueous solution is analyzed for cyanide ion by silver nitrate titrimetric method or an ion-selective electrode method, and ammonia is measured by titration or electrode technique.

Notes

  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.

Related Research Articles

Cyanide Any chemical compound with cyanide anion

A cyanide is a chemical compound that contains the group C≡N. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the chemical formula HCN. It is a colorless, extremely poisonous, 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.

Ammonium Polyatomic ion

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+
4. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged or protonated substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic groups.

Potassium ferricyanide Chemical compound

Potassium ferricyanide is the chemical compound with the formula K3[Fe(CN)6]. This bright red salt contains the octahedrally coordinated [Fe(CN)6]3− ion. It is soluble in water and its solution shows some green-yellow fluorescence. It was discovered in 1822 by Leopold Gmelin,

Hydroxylamine Inorganic compound

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Potassium cyanide Chemical compound

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Formamide Chemical compound

Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.

Ammonium bromide Chemical compound

Ammonium bromide, NH4Br, is the ammonium salt of hydrobromic acid. The chemical crystallizes in colorless prisms, possessing a saline taste; it sublimes on heating and is easily soluble in water. On exposure to air it gradually assumes a yellow color because of the oxidation of traces of bromide (Br−) to bromine (Br2).

Ammonium chlorate Chemical compound

Ammonium chlorate is an inorganic compound with the formula NH4ClO3.

Ammonium nitrite Chemical compound

Ammonium nitrite, NH4NO2, is the ammonium salt of nitrous acid. It is not used in pure isolated form since it is highly unstable and decomposes into water and nitrogen, even at room temperature.

An inorganic nonaqueous solvent is a solvent other than water, that is not an organic compound. These solvents are used in chemical research and industry for reactions that cannot occur in aqueous solutions or require a special environment. Inorganic nonaqueous solvents can be classified into two groups, protic solvents and aprotic solvents. Early studies on inorganic nonaqueous solvents evaluated ammonia, hydrogen fluoride, sulfuric acid, as well as more specialized solvents, hydrazine, and selenium oxychloride.

Mercury(II) cyanide Chemical compound

Mercury(II) cyanide, also known as mercuric cyanide, is a compound of mercury. It is an odorless, toxic white powder. It is highly soluble in polar solvents such as water, alcohol, and ammonia; slightly soluble in ether; and insoluble in benzene and other hydrophobic solvents.

Chloroplatinic acid Chemical compound

Chloroplatinic acid (also known as hexachloroplatinic acid) is an inorganic compound with the formula [H3O]2[PtCl6](H2O)x (0 ≤ x ≤ 6). A red solid, it is an important commercial source of platinum, usually as an aqueous solution. Although often written in shorthand as H2PtCl6, it is the hydronium (H3O+) salt of the hexachloroplatinate anion (PtCl2−
6). Hexachloroplatinic acid is highly hygroscopic.

Zinc cyanide Chemical compound

Zinc cyanide is the inorganic compound with the formula Zn(CN)2. It is a white solid that is used mainly for electroplating zinc but also has more specialized applications for the synthesis of organic compounds.

Ammonium formate Chemical compound

Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.

Ammonium thiocyanate Chemical compound

Ammonium thiocyanate is an inorganic compound with the formula NH4SCN. It is the salt of the ammonium cation and the thiocyanate anion.

Ammonium carbamate Chemical compound

Ammonium carbamate is an organic compound with the formula NH4[H2NCO2] consisting of ammonium NH+
4 and carbamate H
2NCO−
2. It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia with carbon dioxide, and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediary in the industrial synthesis of urea, an important fertilizer.

Nickel dicyanide is the inorganic compound with a chemical formula Ni(CN)2. It is a gray-green solid that is insoluble in most solvents.

References

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