 | This article may be too technical for most readers to understand. (August 2022) |
 Depiction of the all-phosphorus analogue of benzene
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| Names | |
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| IUPAC name
hexaphosphinine
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| P6 | |
| Molar mass | 185.842571988 g·mol−1 |
| Related compounds | |
Related compounds
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Benzene Hexazine Borazine Carborazine Aluminazine Caraluminazine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hexaphosphabenzene is a valence isoelectronic analogue of benzene and is expected to have a similar planar structure due to resonance stabilization and its sp2 nature. Although several other allotropes of phosphorus are stable, no evidence for the existence of P6 has been reported. Preliminary ab initio calculations on the trimerisation of P2 leading to the formation of the cyclic P6 were performed, and it was predicted that hexaphosphabenzene would decompose to free P2 with an energy barrier of 13−15.4 kcal mol−1,[1] and would therefore not be observed in the uncomplexed state under normal experimental conditions. The presence of an added solvent, such as ethanol, might lead to the formation of intermolecular hydrogen bonds which may block the destabilizing interaction between phosphorus lone pairs and consequently stabilize P6.[1] The moderate barrier suggests that hexaphosphabenzene could be synthesized from a [2+2+2] cycloaddition of three P2 molecules.[2] Currently, this is a synthetic endeavour which remains to be conquered.
- ^ a b Nguyen, Minh Tho; Hegarty, Anthony F. (1986-01-01). "Can the cyclic hexaphosphabenzene (P6) exist?". Journal of the Chemical Society, Chemical Communications (5): 383–385. doi:10.1039/C39860000383. ISSN 0022-4936.
- ^ Nagase, Shigeru; Ito, Keiji (1986-04-25). "Theoretical study of hexaphosphabenzene and its valence isomers. Is cyclic P6 stable?". Chemical Physics Letters. 126 (1): 43–47. Bibcode:1986CPL...126...43N. doi:10.1016/0009-2614(86)85113-2. ISSN 0009-2614.