Borabenzene is a hypothetical organoboron compound with the formula C5H5B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the boratabenzene anions, including the parent [C5H5BH]−.
Adducts of borabenzene with Lewis bases are isolatable. Since borabenzene is unavailable, these adducts require indirect methods. 4-Silyl-1-methoxyboracyclohexadiene is used as a precursor to the borabenzene:
C 5H 5N + MeOBC 5H 5SiMe 3 → C 5H 5N-BC 5H 5 + MeOSiMe3
The pyridine adduct C 5H 5N-BC 5H 5 is structurally related to biphenyl.[1] It is a yellow whereas biphenyl is colorless, indicating distinct electronic structures. The pyridine ligand is tightly bound: no exchange is observed with free pyridine, even at elevated temperatures.
Adducts of borabenzene with pyridine and triphenylphosphine.
^Boese, Roland; Finke, Norbert; Henkelmann, Jochem; Maier, Günther; Paetzold, Peter; Reisenauer, Hans Peter; Schmid, Günter (1985). "Synthese und Strukturuntersuchung von Pyridin-Borabenzol und Pyridin-2-Boranaphthalin". Chemische Berichte. 118 (4): 1644–1654. doi:10.1002/cber.19851180431.
^Wood, Thomas K.; Piers, Warren E.; Keay, Brian A.; Parvez, Masood (2006). "1-Borabarrelene Derivatives via Diels−Alder Additions to Borabenzenes". Organic Letters. 8 (13): 2875–2878. doi:10.1021/ol061201w. PMID 16774279.
April 09, 2024
borabenzene, hypothetical, organoboron, compound, with, formula, c5h5b, unlike, related, highly, stable, benzene, molecule, borabenzene, would, electron, deficient, related, derivatives, boratabenzene, anions, including, parent, c5h5bh, namespreferred, iupac, . Borabenzene is a hypothetical organoboron compound with the formula C5H5B Unlike the related but highly stable benzene molecule borabenzene would be electron deficient Related derivatives are the boratabenzene anions including the parent C5H5BH Borabenzene NamesPreferred IUPAC name BorinineIdentifiersCAS Number 31029 61 53D model JSmol Interactive imageChemSpider 9074474PubChem CID 10899214CompTox Dashboard EPA DTXSID50447608InChI InChI 1S C5H5B c1 2 4 6 5 3 1 h1 5HKey HXNZTJULPKRNPR UHFFFAOYSA NSMILES B1 CC CC C1PropertiesChemical formula C 5H 5BMolar mass 75 91 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesAdducts editAdducts of borabenzene with Lewis bases are isolatable Since borabenzene is unavailable these adducts require indirect methods 4 Silyl 1 methoxyboracyclohexadiene is used as a precursor to the borabenzene C5 H5 N MeOBC5 H5 SiMe3 C5 H5 N BC5 H5 MeOSiMe3The pyridine adduct C5 H5 N BC5 H5 is structurally related to biphenyl 1 It is a yellow whereas biphenyl is colorless indicating distinct electronic structures The pyridine ligand is tightly bound no exchange is observed with free pyridine even at elevated temperatures nbsp Adducts of borabenzene with pyridine and triphenylphosphine The borabenzene pyridine adduct behaves like a diene not an analog of biphenyl and will undergo Diels Alder reactions 2 nbsp See also edit6 membered aromatic rings with one carbon replaced by another group silabenzene germabenzene stannabenzene pyridine phosphorine arsabenzene stibabenzene bismabenzene pyrylium thiopyrylium selenopyrylium telluropyrylium BorazineReferences edit Boese Roland Finke Norbert Henkelmann Jochem Maier Gunther Paetzold Peter Reisenauer Hans Peter Schmid Gunter 1985 Synthese und Strukturuntersuchung von Pyridin Borabenzol und Pyridin 2 Boranaphthalin Chemische Berichte 118 4 1644 1654 doi 10 1002 cber 19851180431 Wood Thomas K Piers Warren E Keay Brian A Parvez Masood 2006 1 Borabarrelene Derivatives via Diels Alder Additions to Borabenzenes Organic Letters 8 13 2875 2878 doi 10 1021 ol061201w PMID 16774279 Retrieved from https en wikipedia org w index php title Borabenzene amp oldid 1039106441, wikipedia, wiki, book, books, library,
