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.[1][2][3]
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| Preferred IUPAC name
Bismine | |
| Other names
Bismin
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C5H5Bi | |
| Molar mass | 274.075 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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An unstable derivative with 4-alkyl substituents was reported in 1982.[4] A stable derivative, with two ortho tri(isopropyl)silyl substituents, was synthesized from aluminacyclohexadiene, bismuth trichloride, and DBU in 2016.[1][5]
References
edit- ^ a b Fernando Gomollon-Bel (September 29, 2016). "Chemists create stable bismuth benzene derivative". Chemistry World.
- ^ 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.
- ^ 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).
- ^ 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.
- ^ 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.