Arsabenzene
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Preferred IUPAC name
Arsinine
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Systematic IUPAC name
Arsinine
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| Other names
Arsabenzene
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C5H5As | |
| Molar mass | 140.02 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 | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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).
This air sensitive liquid has an onion odor, and it decomposes on heating. Arsabenzene is also an ambidentate ligand, and it 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.
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.
NMR spectroscopy carried out on arsabenzene indicates that it has a diamagnetic ring current.
Arsabenzene is synthesized in a two step process from 1,4-pentadiyne. The diyne reacts with dibutylstannane to give 1,1-dibutylstannacyclohexa-2,5-diene. The organotin compound undergoes As/Sn exchange with arsenic trichloride to give 1-chloroacyclohexadiene, which loses a HCl upon heating, forming the arsabenzene.
Arsabenzene undergoes electrophilic aromatic substitution at its ortho and para positions. It also undergoes Friedel-Crafts acylation.
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