Arsabenzene

Arsabenzene (IUPAC name: arsinine) is an organoarsenic heterocyclic compound with the chemical formula C5H5As. It belongs to a group of compounds called heteroarenes that have the general formula C5H5E (E= N, P, As, Sb, Bi).

Arsabenzene
Names
Preferred IUPAC name
Arsinine
Systematic IUPAC name
Arsinine
Other names
Arsabenzene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H5As/c1-2-4-6-5-3-1/h1-5H Y
    Key: XRFXFAVKXJREHL-UHFFFAOYSA-N Y
  • InChI=1/C5H5As/c1-2-4-6-5-3-1/h1-5H
    Key: XRFXFAVKXJREHL-UHFFFAOYAM
  • C1=CC=[As]C=C1
Properties
C5H5As
Molar mass 140.017 g·mol−1
Appearance Colourless gas
Odor Onion like
Melting point −54 °C (−65 °F; 219 K)
Boiling point −54 to 25 °C (−65 to 77 °F; 219 to 298 K)
Structure
planar
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

This air sensitive liquid has an onion odor, and it decomposes on heating. Arsabenzene is also an ambidentate ligand that prefers to coordinate using η1(As)- or η6(π)-routes.

The study of arsabenzene and related compounds was an important step in the understanding of compounds that contain multiple bonds between carbon and heavier elements.

The study of heteroarenes was begun by Märkl, with the synthesis of 2,4,6-triphenylphosphabenzene. This is achieved by treating 2,4,6-trisubstituted pyrylium salt with phosphanes. The first derivative of arsabenzene was 9-arsaanthracene prepared by Jutzi and Bickelhaupt.

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