Abstract
AbstractThe basicity of a family of 2,5‐dihydropyrrolimines is examined by the Hartree‐Fock model. It is found that these systems exhibit high proton affinity, which increases with the number of the five‐membered rings present. The origin of the pronounced basicity is identified as the tandem or domino aromatic effect occurring in the conjugate acids. The aromatization is triggered by protonation and spread over whole systems via mobile π‐electrons. Proton affinities as high as 300 kcal/mol or more can be achieved in the gas phase, if the aromatization is combined with the favourable substituent effects and with the intramolecular hydrogen bond corona effect. Copyright © 2002 John Wiley & Sons, Ltd.
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