Sodium cyanate (NaOCN) is a white crystalline solid that adopts a body centered rhombohedral crystal lattice structure (
trigonal crystal system
In crystallography, the hexagonal crystal family is one of the six crystal families, which includes two crystal systems (hexagonal and trigonal) and two lattice systems (hexagonal and rhombohedral). While commonly confused, the trigonal crystal ...
) at room temperature.
Preparation
Sodium cyanate is prepared industrially by the reaction of
urea
Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
Urea serves an important r ...
with
sodium carbonate
Sodium carbonate, , (also known as washing soda, soda ash and soda crystals) is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield moderately alkaline solutions ...
at elevated temperature.
:2OC(NH
2)
2 + Na
2CO
3 → 2Na(NCO) + CO
2 + 2NH
3 + H
2O
It can also be prepared in the laboratory by oxidation of a cyanide in aqueous solution by a mild oxidizing agent such as
lead oxide
Lead oxides are a group of inorganic compounds with formulas including lead (Pb) and oxygen (O).
Common lead oxides include:
* Lead(II) oxide, PbO, litharge (red), massicot (yellow)
* Lead(II,IV) oxide, Pb3O4, minium, ''red lead''
* Lead dioxide ...
.
Chemical Uses
Sodium cyanate is an ideal
nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
, and these nucleophilic properties make it a major contributor to the
stereospecificity
In chemistry, stereospecificity is the property of a reaction mechanism that leads to different stereoisomeric reaction products from different stereoisomeric reactants, or which operates on only one (or a subset) of the stereoisomers."Overlap Co ...
in certain reactions such as in the production of chiral
oxazolidone
2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.
Oxazolidinones
Evans auxiliaries
Oxazolidinones are a class of compounds containing 2-oxazolidone in the structure. In chemistry, they are ...
.
Medical applications
Sodium cyanate is a useful reagent in producing asymmetrical urea derivatives that have a range of
biological activity
In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...
mostly in aryl
isocyanate
In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...
intermediates.
Such intermediates as well as sodium cyanate have been used in medicine as a means of counterbalancing carcinogenic effects on the body, possibly helping people with
sickle cell anemia
Sickle cell disease (SCD) is a group of blood disorders typically inherited from a person's parents. The most common type is known as sickle cell anaemia. It results in an abnormality in the oxygen-carrying protein haemoglobin found in red blo ...
,
[STUDIES WITH INTRAVENOUS SODIUM CYANATE IN PATIENTS WITH SICKLE CELL ANEMIA. Charles M. Peterson, Yang S. Lu, John T. Herbert, Anthony Cerami, and Peter N. Gillette. ''Journal of Pharmacological Experimental Therapy'' June. 1974 189:577-584; published online June 1, 1974,] and blocking certain receptors for
melanin
Melanin (; from el, μέλας, melas, black, dark) is a broad term for a group of natural pigments found in most organisms. Eumelanin is produced through a multistage chemical process known as melanogenesis, where the oxidation of the amino ...
which has been shown to help with obesity.
See also
*
Cyanate
Cyanate is an anion with the structural formula , usually written . It also refers to any salt containing it, such as ammonium cyanate.
It is an isomer of the much less stable fulminate anion .William R. Martin and David W. Ball (2019): "Small ...
References
Cyanates
Sodium compounds
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