Effects of the (Trialkyl)ammonium Structures in (Ammonio)amidyl Groups on π-Electron Donating Ability and Thermal Stability: Experimental and Computational Study.

The (ammonio)amidyl (AA) groups, with the general structure of R3N+N--, represent a new class of π-electron-donating groups for the benzene-based π-conjugated molecules. This study investigated AA-substituted p-nitrobenzenes to assess the effects of acyclic, monocyclic, and bicyclic ammonium structures in the AA groups on the π-electron-donating ability and thermal stability of the structure. Quantum chemical calculations were performed that supported the experimentally observed favorable properties of the (quinuclidinio)amidyl (QA) group.