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

✍ Scribed by Zvonimir B. Maksić; Robert Vianello

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 233 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300810

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✦ Synopsis

Abstract

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 the propyl−BX~2~ chain, where X = F, Cl and Br, and the O^−^ atom in the corresponding conjugate bases. 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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