Phosphorine

Not to be confused with phosphine.
Phosphorine
Kekulé skeletal formula of phosphorine
Kekulé skeletal formula of phosphorine
Aromatic ball and stick model of phosphorine
Aromatic ball and stick model of phosphorine
Names
Preferred IUPAC name
Phosphinine[1]
Other names
Phosphabenzene
Identifiers
3D model (JSmol)
ChemSpider
MeSH Phosphinine
UNII
  • InChI=1S/C5H5P/c1-2-4-6-5-3-1/h1-5H checkY
    Key: UNQNIRQQBJCMQR-UHFFFAOYSA-N checkY
  • InChI=1/C5H5P/c1-2-4-6-5-3-1/h1-5H
    Key: UNQNIRQQBJCMQR-UHFFFAOYAZ
  • C1=CC=PC=C1
Properties
C5H5P
Molar mass 96.069 g·mol−1
Related compounds
Related -ines
Related compounds
 Phosphole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 an air-sensitive oil[2] but is otherwise stable when handled using air-free techniques (however, substituted derivatives can often be handled under air without risk of decomposition).[3][4] 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.

  1. ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4. p. 47.
  2. ^ Cite error: The named reference Ashe was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  4. ^ Newland, R. J.; Wyatt, M. F.; Wingad, R. L.; Mansell, S. M. (2017). "A ruthenium(II) bis(phosphinophosphinine) complex as a precatalyst for transfer-hydrogenation and hydrogen-borrowing reactions". Dalton Transactions. 46 (19): 6172–6176. doi:10.1039/C7DT01022B. hdl:1983/8ceafa01-697c-4055-bd9f-3bfcb60d93f2. ISSN 1477-9226. PMID 28436519.