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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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Ammonium cyanate is an inorganic compound with the formula [NH4]+[OCN]−. It is a colorless, solid salt.
Structure and reactions
[edit]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]
NH+4 + OCN− → (NH2)2CO[3]This is generally credited as the first total synthesis of an organic compound. Wöhler's work with ammonium cyanate is sometimes credited for ending support for vitalism in the sciences, but this account has been criticised by both historians and chemists as reductive.[4][5]
References
[edit]- ^ 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.
- ^ 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 on Reaction mechanisms". Chemical Society Reviews. 7: 1–14. doi:10.1039/CS9780700001.
- ^ Ramberg, Peter J. (2000). "The Death of Vitalism and the Birth of Organic Chemistry: Wohler's Urea Synthesis and the Disciplinary Identity of Organic Chemistry". Ambix. 47 (3): 170–195. doi:10.1179/amb.2000.47.3.170. PMID 11640223.
- ^ Brooke, John H. (1968). "Wöhler's Urea, and its Vital Force ?—A Verdict from the Chemists". Ambix. 15 (2): 84–114. doi:10.1179/amb.1968.15.2.84.
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