The conclusions from our electronic structure studies of complexes 8 (thiolate), 9 (amide), versus an atypical small |ΔEQ| is observed. Independently, the relatively low distortion from planarity, strong π donation from the amide ligand, and short Fe-N bond in 9 are hypothesized to enact relative orbital energies that are amenable to changing order in the presence of a cation.