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| - Formation of Para-Substituted Triphenylboroxines: A Computational Study
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| - Density functional theory (B3LYP//6-311+G*) calculations including Poisson−Boltzmann (PB) implicit solventwere applied to study the relative stability of triphenylboroxine (PhBO)3 with respect to its phenylboronicacid monomers. In solution, formation of (PhBO)3 is thermodynamically unfavorable; however, addition ofan amine base results in the formation of stable 1:1 adducts of (PhBO)3 and amine. Formation of 1:2 adductsis energetically unfavorable. We find that adduct formation is more exothermic than cleavage of the boroxinering back to its monomers. π-Electron-withdrawing groups in the para-position of the phenyl ring destabilizethe boroxine ring with respect to its monomers. However, para-substituents that are net electron-withdrawingare found to stabilize formation of the 1:1 adduct.
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