Abstract
Stabilities of aromatic cations are governed by inductive and resonance effects of ring substituents, which are well described by the Yukawa-Tsuno equation. On the other hand, LFER for anionic systems has not yet been established due to experimental difficulties. Recently, we introduced theoretical method to investigate anions. In the preceding symposiums, we reported that the stabilities of benzylic anions and phenylamide anions are governed by inductive, resonance, and saturation effects, and an extended Yukawa-Tsuno equation was proposed for these anionic systems. In order to establish generality of this equation, more extensive analyses on various anionic species are desirable. In this point of view, we extended this type of research to phenoxide ions. We used proton transfer equilibria to determine the relative gas phase stabilities of ring substituted phenoxide ions. Energies of species in these equilibria were calculated by means of DFT method. We compared substituent effects of phenoxide ion with various benzylic anions. Detailed statistical analyses confirmed that an extended Yukawa-Tsuno equation reported is also necessary to describe substituent effects of phenoxide ion.
