Arsabenzene

Arsabenzene
Names
	Preferred IUPAC name Arsinine
	Systematic IUPAC name Arsinine
	Other names Arsabenzene
Identifiers
CAS Number	289-31-6 ;
3D model ( JSmol)	Interactive image;
ChemSpider	119909 ;
PubChem CID	136132;
CompTox Dashboard (EPA)	DTXSID90183093 ;
	InChI InChI=1S/C5H5As/c1-2-4-6-5-3-1/h1-5H Key: XRFXFAVKXJREHL-UHFFFAOYSA-N ; InChI=1/C5H5As/c1-2-4-6-5-3-1/h1-5H Key: XRFXFAVKXJREHL-UHFFFAOYAM;
	SMILES C1=CC=[As]C=C1;
Properties
Chemical formula	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
Molecular shape	planar
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Arsabenzene (

heteroarenes that have the general formula C₅H₅E (E= N, P, As, Sb, Bi).^[1]

This air sensitive liquid has an onion odor,

ambidentate ligand that prefers to coordinate using η¹(As)- or η⁶(π)-routes.^[3]

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.^[4]

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

phosphanes.^[4] The first derivative of arsabenzene was 9-arsaanthracene prepared by Jutzi and Bickelhaupt.^[5]

Structure

Arsabenzene is planar. The C—C bond distances of 1.39 Å, the As—C bond has a length of 1.85 Å, this is 6.6% shorter than the normal As—C single bond.[1]

stibabenzene, and bismabenzene

diamagnetic ring current.^[6]

Synthesis

Arsabenzene is synthesized in a two step process from 1,4-pentadiyne. The

organotin compound undergoes As/Sn exchange with arsenic trichloride to give 1-chloroacyclohexadiene, which loses a HCl upon heating, forming the arsabenzene.^[1]

CH₂(CHCH)₂SnBu₂ + AsCl₃ → CH₂(CHCH)₂AsCl + Bu₂SnCl₂

CH₂(CHCH)₂AsCl → C₅H₅As + HCl