Cyaphide, , is the phosphorus analogue of

cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...

. It is not known as a discrete

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

; however, ''

in silico In biology and other experimental sciences, an ''in silico'' experiment is one performed on a computer or via computer simulation software. The phrase is pseudo-Latin for 'in silicon' (correct ), referring to silicon in computer chips. It was c ...

'' measurements reveal that the −1 charge in this ion is located mainly on carbon (0.65), as opposed to phosphorus. The word "cyaphide" was first coined in 1992, by analogy with cyanide.

Preparation

Organometallic complexes of cyaphide were first reported in 1992. More recent preparations use two other routes:

From -functionalised phosphaalkynes

Treatment of the η¹-coordinated phosphaalkyne complex ''trans''– with an alkoxide resulted in desilylation, followed by subsequent rearrangement to the corresponding carbon-bound cyaphide complex. Cyaphide-alkynyl complexes are prepared similarly.

From 2-phosphaethynolate anion ()

An actinide cyaphide complex can be prepared by C−O bond cleavage of the phosphaethynolate anion, the phosphorus analogue of cyanate. Reaction of the uranium complex [] with [ in the presence of 2.2.2-cryptand results in the formation of a dinuclear, oxo-bridged uranium complex featuring a C≡P ligand.

References

{{reflist Anions Phosphorus compounds

Preparation

From -functionalised phosphaalkynes

From 2-phosphaethynolate anion ()

See also

References