Cyaphide
Chemical compound
From Wikipedia, the free encyclopedia
Cyaphide, −C≡P, is the phosphorus analogue of cyanide. It is not known as a discrete salt; however, in silico measurements reveal that the −1 charge in this ion is located mainly on carbon (0.65), as opposed to phosphorus.
| −C≡P | |
| Names | |
|---|---|
| IUPAC name
Cyaphide | |
| Other names
Methanidylidynephosphane | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| Properties | |
| CP− | |
| Molar mass | 42.985 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The word "cyaphide" was first coined in 1992, by analogy with cyanide.[1]
Preparation
Organometallic complexes of cyaphide were first reported in 1992.[2] More recent preparations use two other routes:
From SiR3-functionalised phosphaalkynes
Treatment of the η1-coordinated phosphaalkyne complex trans–[RuH(P≡CSiPh3)(dppe)2]+ with an alkoxide resulted in desilylation, followed by subsequent rearrangement to the corresponding carbon-bound cyaphide complex.[3] Cyaphide-alkynyl complexes are prepared similarly.[4]
From 2-phosphaethynolate anion (−O−C≡P)
An actinide cyaphide complex can be prepared by C−O bond cleavage of the phosphaethynolate anion, the phosphorus analogue of cyanate.[5] Reaction of the uranium complex [((Ad,MeArO)3N)UIII(DME)] with [Na(OCP)(dioxane)2.5] in the presence of 2.2.2-cryptand results in the formation of a dinuclear, oxo-bridged uranium complex featuring a C≡P ligand.
See also
- Phosphaalkyne (R−C≡P)
- Methylidynephosphane (H−C≡P)
- Cyanide
- Cyaarside