Reactivities of 19 methylated imidate analogs were examined using B3LYP and M06-2X DFT methods. The resulting HOMO and LUMO energies of each optimized structure were used to calculate corresponding Parr global electrophilicity (ω) values. When the resulting quantities were compared against Boyd group electronegativity (XG) values, a clear correlation was observed, suggesting that electron-withdrawing effects influence the reactivity of imidates. These findings represent an important first step in developing a novel method toward improving traditional Mitsunobu functionalization reactions.