Bismabenzene

Bismabenzene
Names
Preferred IUPAC name
Bismine
Other names
Bismin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H5Bi/c1-2-4-6-5-3-1/h1-5H
    Key: ZEBPXYQZSWNMLH-UHFFFAOYSA-N
  • C1=CC=[Bi]C=C1
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).

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]

Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene[clarification needed]

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

  1. ^ a b 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.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.