Ammonium cyanate

Ionic chemical compound with formula [NH4]+ [OCN]-
Ammonium cyanate
Identifiers
CAS Number
  • 22981-32-4
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2339431
PubChem CID
  • 9793686
CompTox Dashboard (EPA)
  • DTXSID40177528 Edit this at Wikidata
InChI
  • InChI=1S/CHNO.H3N/c2-1-3;/h3H;1H3
    Key: QYTOONVFPBUIJG-UHFFFAOYSA-N
  • C(#N)[O-].[NH4+]
Properties
Chemical formula
 [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
Chemical compound

Ammonium cyanate is an inorganic compound with the formula [NH4]+[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 [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 (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. 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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Ammonium salts
Inorganic salts
monatomic anions
  • NH4F
  • (NH4)2S
  • NH4Cl
  • (NH4)2Se
  • NH4Br
  • NH4I
oxyanions
  • NH4NO2
  • NH4NO3
  • (NH4)2CO3
  • (NH4)4UO2(CO3)2
  • (NH4)HCO3
  • NH4OCN
  • (NH4)3PO4
  • (NH4)2HPO4
  • (NH4)H2PO4
  • (NH4PO4)n(OH)2
  • NH4NaHPO4
  • (NH4)2SO3
  • (NH4)2SO4
  • (NH4)Al(SO4)2·12H2O
  • (NH4)2Fe(SO4)2·6H2O
  • NH4Fe(SO4)2·12H2O
  • NH4SO3NH2
  • (NH4)HSO4
  • (NH4)2S2O8
  • (NH4)2S2O3
  • NH4ClO3
  • NH4ClO4
  • NH4VO3
  • (NH4)2CrO4
  • (NH4)2Cr2O7
  • NH4MnO4
  • (NH4)3AsO4
  • (NH4)2MoO4
  • (NH4)6Mo7O24
  • (NH4)3Mo12PO40
  • NH4IO3
  • (NH4)2Ce(NO3)6
  • (NH4)8Ce2(SO4)8·4H2O
  • (NH4)10H2W12O42·4H2O
  • NH4ReO4
other anions
  • NH4BF4
  • NH4N3
  • NH4CN
  • (NH4)HF2
  • (NH4)3AlF6
  • (NH4)SiF6
  • (NH4)HS
  • NH4SCN
  • (NH4)2ZnCl4
  • (NH4)2MoS4
  • NH4I3
  • (NH4)2TeCl6
  • (NH4)2IrCl6
  • (NH4)2PtCl6
Organic salts
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Salts and covalent derivatives of the cyanate ion
HNCO He
LiOCN Be B C NH4OCN OCN−
-NCO
O(CN)2 		F Ne
NaOCN Mg(OCN)2 Al Si(OCN)4 P S Cl Ar
KOCN Ca(OCN)2 Sc Ti V Cr Mn Fe Co(OCN)2 Ni CuOCN Zn Ga Ge As Se Br Kr
RbOCN Sr(OCN)2 Y Zr Nb Mo Tc Ru Rh Pd AgOCN Cd In Sn Sb Te I Xe
CsOCN Ba(OCN)2 * Lu Hf Ta W Re Os Ir Pt Au Hg TlOCN Pb(OCN)2 Bi Po At Rn
Fr Ra ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La Ce Pr Nd Pm Sm Eu(OCN)2 Gd Tb Dy Ho Er Tm Yb
** Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No


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