Arsabenzene

Arsabenzene
Structural formula of arsabenzene
Space-filling model of 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 checkY
    Key: XRFXFAVKXJREHL-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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).[1]

This air sensitive liquid has an onion odor,[2] and it decomposes on heating.[1] Arsabenzene is also an 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 pyrylium salt with phosphanes.[4] The first derivative of arsabenzene was 9-arsaanthracene prepared by Jutzi and Bickelhaupt.[5]

  1. ^ a b Elschenbroich, C. (2006). Organometallics (in German). Wiley-VCH Weinheim. pp. 229–230. ISBN 3-527-29390-6.
  2. ^ Cadogan, J. I. G.; Buckingham, J.; Macdonald, F. (1997). Dictionary of Organic Compounds. Vol. 10 (6th ed.). CRC Press. p. 491. ISBN 0-412-54110-6.
  3. ^ Sadimenko, A. P. (2005). Organometallic Complexes of B-, Si- (Ge-), and P- (As-, Sb-) Analogues of Pyridine. Advances in Heterocyclic Chemistry. Vol. 89. pp. 125–157. doi:10.1016/S0065-2725(05)89003-8. ISBN 9780120207893.
  4. ^ a b Eicher, T.; Hauptmann, S.; Suschitzky, H.; Suschitzky, J. (2003). The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications (in German) (2nd ed.). Wiley-VCH Weinheim. p. 368. ISBN 3-527-30720-6.
  5. ^ Ashe, A. J. (1978). "The Group 5 Heterobenzenes". Accounts of Chemical Research. 11 (4): 153–157. doi:10.1021/ar50124a005.