Chemistry:Ammonium cyanate

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Short description: Ionic chemical compound with formula [NH4]+ [OCN]-
Ammonium cyanate
NH4OCN.png
Ammonium-cyanate-3D-vdW.png
Ammonium-cyanate-xtal-Mercury-3D-balls.png
Identifiers
3D model (JSmol)
ChemSpider
Properties
[NH
4
][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

Ammonium cyanate is an inorganic compound with the formula [NH
4
]+
[OCN]
. It is a colorless, solid salt.

Structure and reactions

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 [NH
4
]+
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
→ (NH
2
)
2
CO
[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 (47): 14449–14451. doi:10.1021/ja021156x. PMID 14624593. 
  2. Friedrich Wöhler (1828). "Ueber künstliche Bildung des Harnstoffs". Annalen der Physik und Chemie 88 (2): 253–256. doi:10.1002/andp.18280880206. Bibcode1828AnP....88..253W. http://gallica.bnf.fr/ark:/12148/bpt6k15097k/f261.chemindefer. 
  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.