Transition metal complexes have been extensively investigated as catalysts for small molecule activation due to their tunable reactivity through diverse chemical modifications. Biomimetic complexes, inspired by enzymatic active sites, exhibit high catalytic efficiency attributable to structural variations within their secondary coordination spheres. These motifs, including external charges and proton relay groups, have been demonstrated to influence catalytic activity even though they are not directly coordinate to the metal center. In this study, iron complexes supported by pyridine-amine donors, featuring appended partial crown ether rings or polyethylene glycol chains, are presented. The reported iron complexes exhibited binding of the ligands with transition metals at the pyridine and amine donors, while the crown ether or polyethylene glycol moieties demonstrated binding of several cations (alkali, alkaline earth, and lanthanum metal ions) with varying binding affinities. The addition of varying positive charges resulted in a cathodic shift of the iron complex's redox potential. Iron complexes with open-chain ligands displayed significantly less affinity toward monovalent cations. Correlations between charges and ionic radii of cations were established. The catalytic activities for C-H bond activation showed a preference for O-atom transfer rather than H-atom abstraction in the presence of more Lewis acidic cations.