Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

with a

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atom replaced by a

bismuth Bismuth is a chemical element; it has symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental bismuth occurs nat ...

atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, tending to instead

dimerize In chemistry, dimerization is the process of joining two identical or similar Molecular entity, molecular entities by Chemical bond, bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dim ...

in a Diels-Alder addition. Bond lengths of group 15 heterobenzenes and benzene

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 Bismuth chloride (or butter of bismuth) is an inorganic compound with the chemical formula BiCl3. It is a covalent compound and is the common source of the Bi3+ ion. In the gas phase and in the crystal, the species adopts a pyramidal structure, i ...

, and

DBU DBU may refer to: Universities * Dallas Baptist University, Dallas, Texas, U.S. * Desh Bhagat University, Mandi Gobindgarh, Punjab, India * Duluth Business University, Duluth, Minnesota, U.S. Other uses * 1,8-Diazabicyclo .4.0ndec-7-ene, an org ...

in 2016.

References

{{reflist, colwidth=30em, refs= {{cite journal , doi = 10.1021/jacs.6b08714, title = An Isolable Bismabenzene: Synthesis, Structure, and Reactivity, year = 2016, last1 = Ishii, first1 = Takuya, last2 = Suzuki, first2 = Katsunori, last3 = Nakamura, first3 = Taichi, last4 = Yamashita, first4 = Makoto, journal = Journal of the American Chemical Society, volume = 138, issue = 39, pages = 12787–12790, pmid = 27654463, url = https://figshare.com/articles/journal_contribution/3859389, url-access = subscription {{cite web , title = Chemists create stable bismuth benzene derivative , author = Fernando Gomollon-Bel , date = September 29, 2016 , url = https://www.chemistryworld.com/news/chemists-create-stable-bismuth-benzene-derivative/1017447.article , publisher = Chemistry World {{cite journal , doi = 10.1021/ja00385a024, title = Stabilization of stibabenzene and bismabenzene by 4-alkyl substituents, year = 1982, last1 = Ashe, first1 = Arthur J., last2 = Diephouse, first2 = Timothy R., last3 = El-Sheikh, first3 = Maher Y., journal = Journal of the American Chemical Society, volume = 104, issue = 21, pages = 5693–5699 {{cite journal , doi = 10.1021/ja00776a063, title = Bismabenzene. Reaction of Group V heteroaromatic compounds with hexafluorobutyne, year = 1972, last1 = Ashe, first1 = Arthur J., last2 = Gordon, first2 = Michael D., journal = Journal of the American Chemical Society, volume = 94, issue = 21, pages = 7596–7597 {{cite journal , last = Ashe , first = A. J. , title = The Group 5 Heterobenzenes , journal = Accounts of Chemical Research , year = 1978 , volume = 11 , issue = 4 , page=156 , doi = 10.1021/ar50124a005 , quote=Bismabenzene is so reactive that is exists in the form of a Diels-Alder dimer (10f) at low temperature (<-10 °C). Organobismuth compounds Bismuth heterocycles Six-membered rings