Ammonium cyanate

Ammonium cyanate is an inorganic compound with the formula [NH4]+[OCN]−. It is a colorless, solid salt.

Ammonium cyanate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CHNO.H3N/c2-1-3;/h3H;1H3
    Key: QYTOONVFPBUIJG-UHFFFAOYSA-N
  • C(#N)[O-].[NH4+]
Properties
[NH4][OCN]
Molar mass 60.056 g·mol−1
Appearance Colorless crystals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Structure and reactions
Conversion of ammonium cyanate into urea

The structure of this salt was verified by X-ray crystallography. The respective C–O and C–N distances are 1.174(8) and 1.192(7) Å, consistent with the O=C=N− description. Ammonium cation [NH4]+ forms hydrogen bonds with cyanate anion O=C=N−, but to N, not to O.[1]

The compound is notable as the precursor in the Wöhler synthesis of urea, an organic compound, from inorganic reactants.[2] This led to the discarding of the Vital force theory, suggested earlier by Berzelius.

NH+4 + OCN− → (NH2)2CO[3]

References
  1. MacLean, Elizabeth J.; Harris, Kenneth D. M.; Kariuki, Benson M.; Kitchin, Simon J.; Tykwinski, Rik R.; Swainson, Ian P.; Dunitz; Jack D. (2003). "Ammonium cyanate shows N-H···N hydrogen bonding, not N-H···O". Journal of the American Chemical Society. 125: 14449–14451. doi:10.1021/ja021156x.
  2. Friedrich Wöhler (1828). "Ueber künstliche Bildung des Harnstoffs". Annalen der Physik und Chemie. 88 (2): 253–256. Bibcode:1828AnP....88..253W. doi:10.1002/andp.18280880206.
  3. Shorter, J. (1978). "The conversion of ammonium cyanate into urea. A saga on Reaction mechanisms". Chemical Society Reviews. 7: 1–14. doi:10.1039/CS9780700001.


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