What is "phosphorine"

n. (context organic chemistry English) An analogue of pyridine in which the nitrogen atom is replaced by one of phosphorus

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. Phosphorine is a planar aromatic compound with 88% of the aromaticity of that of benzene. The P-C bond length is 173 pm and the C-C bond lengths center around 140 pm and show little variation.

Phosphorine is generally stable against air and moisture and can be handled without special inert atmosphere equipment, so it is different from silabenzene, which is usually not only air- and moisture-sensitive but also thermally unstable without extensive steric protection. This stability of phosphorine comes from the close electronegativities of phosphorus (2.1) and carbon (2.5). The physical and chemical properties of metal complexes bearing phosphorine as a ligand as well as phosphorine itself have been studied extensively.