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Design of Strong, Neutral Organic Superacids: DFT‐B3LYP Calculations on Some Isobenzofulvene Derivatives
Author(s) -
Maksić Zvonimir B.,
Vianello Robert
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300810
Subject(s) - chemistry , aromatization , deprotonation , moiety , conjugate , medicinal chemistry , density functional theory , carbon atom , computational chemistry , stereochemistry , organic chemistry , catalysis , ion , alkyl , mathematical analysis , mathematics
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)