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Chemical compound / From Wikipedia, the free encyclopedia
Boroles represent a class of molecules known as metalloles, which are heterocyclic 5 membered rings. As such, they can be viewed as structural analogs of cyclopentadiene, pyrrole or furan, with boron replacing a carbon, nitrogen and oxygen atom respectively. They are isoelectronic with the cyclopentadienyl cation C5H5+(Cp+) and comprise four π electrons. Although Hückel's rule cannot be strictly applied to borole, it is considered to be antiaromatic due to having 4 π electrons.[1] As a result, boroles exhibit unique electronic properties not found in other metalloles.
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Names | |||
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IUPAC name
1H-Borole | |||
Identifiers | |||
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3D model (JSmol) |
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ChemSpider |
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PubChem CID |
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Properties | |||
C4H5B | |||
Molar mass | 63.89 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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The parent unsubstituted compound with the chemical formula C4H4BH has yet to be isolated outside a coordination sphere of transition metals[2]. Substituted derivatives, which have been synthesized, can have various substituents at the 4 carbons and boron[3]. The high electron deficiency leads to interesting reactivities such as metal free hydrogen activation and rearrangments upon cycloaddition which are unobserved in other structural analogues like pyrrole or furan.
Once reduced to the dianion, the borolediide complex gains aromaticity and can then participate in similar reactions as the Cp- anion, including forming sandwich complexes.