Fulminate

Last updated
Fulminate
Fulminate-2D.png
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
239442
PubChem CID
  • InChI=1S/CNO/c1-2-3/q-1 Yes check.svgY
    Key: FEWJPZIEWOKRBE-UHFFFAOYSA-L Yes check.svgY
  • InChI=1S/CNO/c1-2-3/q-1
    Key: USXDFAGDIOXNML-UHFFFAOYSA-N
  • [C-]#[N+][O-]
Properties
CNO
Molar mass 42.018 g·mol−1
Conjugate acid Fulminic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fulminates are chemical compounds which include the fulminate ion (CNO, C≡N+−O). The fulminate ion is a pseudohalic ion because its charge and reactivity are similar to those of the halogens. Due to the instability of the ion, fulminate salts are friction-sensitive explosives. The best known is mercury(II) fulminate, which has been used as a primary explosive in detonators. Fulminates can be formed from metals, such as silver and mercury, dissolved in nitric acid and reacted with ethanol. The weak single nitrogen-oxygen bond is responsible for their instability. Nitrogen very easily forms a stable triple bond to another nitrogen atom, forming nitrogen gas.

Contents

Historical notes

Fulminates were discovered by Edward Charles Howard in 1800. [1] [2] [3] The use of fulminates for firearms was first demonstrated by a Scottish minister, Alexander John Forsyth, who patented his scent-bottle lock in 1807; this was a small container filled with fulminate of mercury. [4] [5] Joshua Shaw determined how to encapsulate them in metal to form a percussion cap, but did not patent his invention until 1822.

In the 1820s, the organic chemist Justus Liebig discovered silver fulminate (AgCNO) and Friedrich Wöhler discovered silver cyanate (AgOCN). They have different properties but the same chemical composition, which led to a bitter dispute finally resolved by Jöns Jakob Berzelius through the concept of isomers. [6]

Compounds

See also

English pronunciation of the word "fulminate"

Related Research Articles

Carbon compounds are defined as chemical substances containing carbon. More compounds of carbon exist than any other chemical element except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are covalent bonds. Carbon is tetravalent but carbon free radicals and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is catenation as the ability to form long carbon chains and rings.

Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

<span class="mw-page-title-main">Mercury(II) fulminate</span> Chemical compound

Mercury(II) fulminate, or Hg(CNO)2, is a primary explosive. It is highly sensitive to friction, heat and shock and is mainly used as a trigger for other explosives in percussion caps and detonators. Mercury(II) cyanate, though its chemical formula is identical, has a different atomic arrangement; the cyanate and fulminate anions are isomers.

<span class="mw-page-title-main">Percussion cap</span> Ignition source in a type of firearm mechanism

The percussion cap or percussion primer, introduced in the early 1820s, is a type of single-use percussion ignition device for muzzle loader firearm locks enabling them to fire reliably in any weather condition. This crucial invention gave rise to the cap lock mechanism or percussion lock system using percussion caps struck by the hammer to set off the gunpowder charge in percussion guns including percussion rifles and cap and ball firearms. Any firearm using a caplock mechanism is a percussion gun. Any long gun with a cap-lock mechanism and rifled barrel is a percussion rifle. Cap and ball describes cap-lock firearms discharging a single bore-diameter spherical bullet with each shot.

In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure N=N+=N. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.

<span class="mw-page-title-main">Beckmann rearrangement</span> Chemical rearrangement

The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams.

<span class="mw-page-title-main">Silver fulminate</span> High explosive used in bang snaps

Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

<span class="mw-page-title-main">Fulminic acid</span> Chemical compound (H−C≡N−O)

Fulminic acid is an acid with the formula HCNO, more specifically H−C≡N+−O. It is an isomer of isocyanic acid and of its elusive tautomer, cyanic acid, and also of isofulminic acid.

Pseudohalogens are polyatomic analogues of halogens, whose chemistry, resembling that of the true halogens, allows them to substitute for halogens in several classes of chemical compounds. Pseudohalogens occur in pseudohalogen molecules, inorganic molecules of the general forms PsPs or Ps–X, such as cyanogen; pseudohalide anions, such as cyanide ion; inorganic acids, such as hydrogen cyanide; as ligands in coordination complexes, such as ferricyanide; and as functional groups in organic molecules, such as the nitrile group. Well-known pseudohalogen functional groups include cyanide, cyanate, thiocyanate, and azide.

<span class="mw-page-title-main">Cyanate</span> Anion with formula OCN and charge –1

The cyanate ion is an anion with the chemical formula OCN. It is a resonance of three forms: [O−C≡N] (61%) ↔ [O=C=N] (30%) ↔ [+O≡C−N2−] (4%).

The Wöhler synthesis is the conversion of ammonium cyanate into urea. This chemical reaction was described in 1828 by Friedrich Wöhler. It is often cited as the starting point of modern organic chemistry. Although the Wöhler reaction concerns the conversion of ammonium cyanate, this salt appears only as an (unstable) intermediate. Wöhler demonstrated the reaction in his original publication with different sets of reactants: a combination of cyanic acid and ammonia, a combination of silver cyanate and ammonium chloride, a combination of lead cyanate and ammonia and finally from a combination of mercury cyanate and cyanatic ammonia.

<span class="mw-page-title-main">Isocyanic acid</span> Chemical compound (H–N=C=O)

Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as H−N=C=O. It is a colourless, volatile and poisonous substance, with a boiling point of 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid (aka. cyanol).

<span class="mw-page-title-main">Contact explosive</span> Substance which explodes when exposed to small amounts of energy

A contact explosive is a chemical substance that explodes violently when it is exposed to a relatively small amount of energy. Though different contact explosives have varying amounts of energy sensitivity, they are all much more sensitive relative to other kinds of explosives. Contact explosives are a part of a group of explosives called primary explosives, which are also very sensitive to stimuli but not to the degree of contact explosives. The extreme sensitivity of contact explosives is due to either chemical composition, bond type, or structure.

Cyanogen bromide is the inorganic compound with the formula (CN)Br or BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds. The compound is classified as a pseudohalogen.

<span class="mw-page-title-main">Potassium fulminate</span> Chemical compound

Potassium fulminate is the potassium salt of the fulminate ion. Its only use, aside from chemical demonstrations, is in the percussion caps for some early rifles. Usually prepared by reacting a potassium amalgam with mercury fulminate, it is much less sensitive due to the ionic bond between potassium and carbon, unlike the weaker covalent bond between mercury and carbon.

In chemistry, an ate complex is a salt formed by the reaction of a Lewis acid with a Lewis base whereby the central atom increases its valence and gains a negative formal charge..

<span class="mw-page-title-main">Hydroxylammonium sulfate</span> Chemical compound

Hydroxylammonium sulfate (NH3OH)2SO4, is the sulfuric acid salt of hydroxylamine. It is primarily used as an easily handled form of hydroxylamine, which is explosive when pure.

Explosophores are functional groups in organic chemistry that give organic compounds explosive properties.

<span class="mw-page-title-main">Silver nitride</span> Chemical compound

Silver nitride is an explosive chemical compound with symbol Ag3N. It is a black, metallic-looking solid which is formed when silver oxide or silver nitrate is dissolved in concentrated solutions of ammonia, causing formation of the diammine silver complex which subsequently breaks down to Ag3N. The standard free energy of the compound is about +315 kJ/mol, making it an endothermic compound which decomposes explosively to metallic silver and nitrogen gas.

<span class="mw-page-title-main">Silver cyanate</span> Chemical compound

Silver cyanate is the cyanate salt of silver. It can be made by the reaction of potassium cyanate with silver nitrate in aqueous solution, from which it precipitates as a solid.

References

  1. Edward Howard (1800). "On a New Fulminating Mercury". Philosophical Transactions of the Royal Society of London . 90 (1): 204–238. doi:10.1098/rstl.1800.0012.
  2. F. Kurzer (1999). "The Life and Work of Edward Charles Howard". Annals of Science . 56 (2): 113–141. doi:10.1080/000337999296445.
  3. "Edward Charles Howard (1774-1816), Scientist and sugar refiner". National Portrait Gallery. 2005-01-05. Archived from the original on 2006-09-25. Retrieved 2006-08-30.
  4. Alexander Forsyth in Encyclopædia Britannica
  5. "Rifled Breech Loader". Globalsecurity.org.
  6. Greenberg, Arthur (2000). A Chemical History Tour . John Wiley & Sons. pp.  198–203. ISBN   0-471-35408-2.