Phosphabenzene
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| Names | |||
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Systematic IUPAC name
Phosphinine
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| Other names
Phosphabenzene
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3D model (JSmol)
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| ChemSpider | |||
| MeSH | Phosphinine | ||
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PubChem CID
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| Properties | |||
| C5H5P | |||
| Molar mass | 96.07 g·mol−1 | ||
| Related compounds | |||
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Related -ines
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Arsabenzene |
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Related compounds
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Phosphole | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Phosphorine (IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is mainly of interest in research.
Phosphorine is generally stable against air and moisture and can be handled without special air-free techniques. In contrast, silabenzene, a related heavy-element analogue of benzene, is not only air- and moisture-sensitive but also thermally unstable without extensive steric protection.
The first phosphorine to be isolated is 2,4,6-triphenylphosphorine. It was synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH2OH)3 and P(SiMe3)3).
The parent (unsubstituted) phosphorine was reported by Arthur J. Ashe III in 1971. Ring-opening approaches have been developed from phospholes.
Structural studies by electron diffraction reveal that phosphorine is a planar aromatic compound with 88% of the aromaticity of that of benzene. Potentially relevant to its high aromaticity are the well matched electronegativities of phosphorus (2.1) and carbon (2.5). The P-C bond length is 173 pm and the C-C bond lengths center around 140 pm and show little variation.
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