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AbstractAbstract
[en] Ion cyclotron resonance techniques are employed to determine the gas-phase Bronsted and Lewis acidities as well as the Bronsted basicity of 1-methyl-1,4-dihydroborabenzene, CH3BC5H6. The ring proton is found to be highly acidic with PA(CH3BC5H5-) = 337 +- 3 kcal/mol. This acidity results from the formation of 6π electron aromatic anion CH3BC5H5-, which is isoelectronic with toluene. Both the Lewis acidity toward F- as a reference base and the proton basicity of the parent molecule suggest that there is little interaction between the diene π system and the electron-deficient boron. This is further confirmed by the similarity of both negative and positive ion chemistry of the borabenzene to that of aliphatic boranes
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Journal of the American Chemical Society; v. 100(12); p. 3737-3742
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