|Systematic IUPAC name
3D model (Jmol)
|Molar mass||96.07 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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).
Structure, bonding, and properties
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.
Although phosphorine and pyridine are structurally similar, phosphorines are far less basic. The pKa's of C5H5PH+ and C5H5NH+ are respectively -16.1 and 5.2. Methyl lithium adds to phosphorus in phosphorine whereas it adds to the 2-position of pyridine.
Coordination complexes bearing phosphorine as a ligand are known. Phosphorines can bind to metals through phosphorus center. Complexes of the diphospha analogue of bipyridine are known. Phosphorines also form pi-complexes, illustrated by V(η6-C5H5P)2.
- 6-membered aromatic rings with one carbon replaced by another group: borabenzene, benzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, pyrylium salt
- "Phosphate-Binding Proteolipid - Compound Summary". The PubChem Project. USA: National Center of Biotechnology Information.
- G. Märkl, 2,4,6-Triphenylphosphabenzol in Angewandte Chemie 78, 907–908 (1966)
- Ashe, A. J. (1971). "Phosphabenzene and Arsabenzene". Journal of the American Chemical Society. 93 (13): 3293–3295. doi:10.1021/ja00742a038.
- Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 544. ISBN 0-08-037941-9.
- François Mathey "Phosphorus Heterocycles" in Modern Heterocyclic Chemistry, First Edition, edited by Julio Alvarez-Builla, Juan Jose Vaquero, José Barluenga, Wiley-VCH, Weinheim, 2011. doi:10.1002/9783527637737.ch23.
- László Nyulászi "Aromaticity of Phosphorus Heterocycles" Chem. Rev., 2001, volume 101, pp 1229–1246. doi:10.1021/cr990321x
- Ashe III, Arthur J.; Smith, Timothy W. "The reaction of phosphabenzene, arsabenzene and stibabenzene with methyllithium." Tetrahedron Letters 1977, volume 18, pp. 407-410. doi:10.1016/S0040-4039(01)92651-6