Misplaced Pages

Bismabenzene

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Bismine)
Bismabenzene
Names
Preferred IUPAC name Bismine
Other names Bismin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5Bi/c1-2-4-6-5-3-1/h1-5HKey: ZEBPXYQZSWNMLH-UHFFFAOYSA-N
SMILES
  • C1=CC=C=C1
Properties
Chemical formula C5H5Bi
Molar mass 274.075 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bismabenzene (C5H5Bi) is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, tending to instead dimerize in a Diels-Alder addition.

Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene

An unstable derivative with 4-alkyl substituents was reported in 1982. A stable derivative, with two ortho tri(isopropyl)silyl substituents, was synthesized from aluminacyclohexadiene, bismuth trichloride, and DBU in 2016.

References

  1. ^ Fernando Gomollon-Bel (September 29, 2016). "Chemists create stable bismuth benzene derivative". Chemistry World.
  2. Ashe, Arthur J.; Gordon, Michael D. (1972). "Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne". Journal of the American Chemical Society. 94 (21): 7596–7597. doi:10.1021/ja00776a063.
  3. Ashe, A. J. (1978). "The Group 5 Heterobenzenes". Accounts of Chemical Research. 11 (4): 156. doi:10.1021/ar50124a005. Bismabenzene is so reactive that is exists in the form of a Diels-Alder dimer (10f) at low temperature (<-10 °C).
  4. Ashe, Arthur J.; Diephouse, Timothy R.; El-Sheikh, Maher Y. (1982). "Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents". Journal of the American Chemical Society. 104 (21): 5693–5699. doi:10.1021/ja00385a024.
  5. Ishii, Takuya; Suzuki, Katsunori; Nakamura, Taichi; Yamashita, Makoto (2016). "An Isolable Bismabenzene: Synthesis, Structure, and Reactivity". Journal of the American Chemical Society. 138 (39): 12787–12790. doi:10.1021/jacs.6b08714. PMID 27654463.
Categories: