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Published on: May 15, 2012
Bis(amino)cyclopropenium Trifluoroborates: Synthesis, Hydrolytic Stability Studies, and DFT Insights
1Department of Chemistry , Brock University , 1812 Sir Isaac Brock Way , St. Catharines , ON L2S 3A1 , Canada.
Abstract:
A simple and direct two-step synthesis of bis(amino)cyclopropenium trifluoroborate (BAC-BF3) derivatives from readily available reagents is reported. Hydrolysis studies revealed these BAC-BF3 derivatives were remarkably stable toward defluorination. Notably, this first study of BAC-BF3 adduct hydrolytic stability establishes the compounds reported herein possess half-lives ( t1/2) exceeding 0.23 × 106 min (∼160 days). Density functional theory (DFT) and quantum theory of atoms in molecules (QTAIM) calculations exploring the basis of this high stability are described.
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