Ammonium cyanate

Ammonium cyanate
Identifiers
CAS Number	22981-32-4;
3D model (JSmol)	Interactive image;
ChemSpider	2339431;
PubChem CID	9793686;
CompTox Dashboard (EPA)	DTXSID40177528 ;
	InChI InChI=1S/CHNO.H3N/c2-1-3;/h3H;1H3 Key: QYTOONVFPBUIJG-UHFFFAOYSA-N;
	SMILES C(#N)[O-].[NH4+];
Properties
Chemical formula	CH4N2O
Molar mass	60.056 g·mol−1
Appearance	white solid
	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 NH₄OCN. It is a colorless solid.

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. NH₄⁺ forms hydrogen bonds to N, but not 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.
${\ce {{NH4(OCN)}-> {(NH2)2CO}}}$ [3]

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References

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.CS1 maint: uses authors parameter (link)
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.
Shorter, J. (1978). "The conversion of ammonium cyanate into urea. A saga in Reaction mechanisms". Chemical Society Reviews. 7: 1–14. doi:10.1039/CS9780700001.

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[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.CS1 maint: uses authors parameter (link)

[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 in Reaction mechanisms". Chemical Society Reviews. 7: 1–14. doi:10.1039/CS9780700001.