Fulminate

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.

Not to be confused with Fulminant or Cyanate.
Fulminate
Names
Systematic IUPAC name
Nitroxylmethanide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
239442
  • InChI=1S/CNO/c1-2-3/q-1 Y
    Key: FEWJPZIEWOKRBE-UHFFFAOYSA-L Y
  • 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).
Infobox references

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
  • Fulminic acid
  • Mercury(II) fulminate
  • Potassium fulminate
  • Silver fulminate

See also
Look up fulminate in Wiktionary, the free dictionary.
  • The cyanate (-OCN) and isocyanate (-NCO) groups have a related structure.
  • The nitrile (-CN) and isocyanide (-NC) groups.
  • The functional group fulminate (-ONC) corresponds to the fulminate ion; if the organic bond is at the other end, the nitrile oxide (-CNO) functional group is obtained instead.
  • Internal ballistics

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.
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