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Design of Strong Neutral Organic Superacids: DFT-B3LYP Calculations on some Isobenzofulvene Derivatives

It is shown that isobenzofulvenes heavily substituted by cyano groups provide very good candidates for neutral organic superacids of unprecedented strength. The latter can be additionally enhanced by the anionic corona effect realized by interaction between propyl– BX2 chain and O– atom in the corresponding conjugate bases, where X=F, Cl and Br. The main reason for the highly pronounced acidity is found, however, in the aromatization of the isobenzofulvene moiety upon deprotonation, which in turn is assisted by the electron withdrawing CN groups.

acidity; superacids; aromaticity; Bronsted acid; Lewis acid-base

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