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Carborane acid
Carborane acid H(CHB11Cl11) is a superacid 〔Note that the image the acidic proton is not the one bonded to the carborane but that it is the counterion not displayed〕 one million times stronger than sulfuric acid.〔That is, the concentration of H+ in a solution of the carborane superacid is a million times higher than in a solution of sulfuric acid.〕 The reason for this high acidity is that the acid anion carborane (CHB11Cl11−) is very stable and substituted with electronegative substituents (the chlorine atoms). H(CHB11Cl11) is the only acid known to protonate C60 fullerene without decomposing it. Additionally, it is the only known anion capable of forming a stable, isolable salt with protonated benzene, C6H7+.
In coordination chemistry carboranes can be used as unique bulky ligand scaffolds. It was recently demonstrated that the same carboranyl moiety can act either as strongly electron-withdrawing or electron-donating substituent, depending on the positional attachment of the cluster to the heteroatom.
The fluorinated analogue of carborane acid, H(CHB11F11), is even stronger than chlorinated carborane acid. It is able to protonate butane to form tert-butyl cation at room temperature.〔http://onlinelibrary.wiley.com/doi/10.1002/anie.201308586/abstract〕〔http://www.ncbi.nlm.nih.gov/pubmed/23875729〕〔http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3833890/〕
== References ==
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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