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This article presents a detailed discussion on medium effect on ionic S(N)2 reactions. Ion pairing and the first solvation shell play the main role on reactivity. Ab initio calculations are used to show that a combination of apolar molecular cavity with polar hydroxyl groups can have catalytic effects on these reactions. The present results open an avenue of development for supramolecular catalysts able to control bimolecular ionic reactions. In particular, this new catalytic concept could be useful in nucleophilic fluorinations.
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Josefredo R. Pliego (2008) studied this question.
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