We then studied the mechanism and regioselectivity of Zincke imine halogenation by Nhalosuccinimides with quantum chemistry at the B3LYP-D3(BJ)/def2-TZVP//ωB97X-D/6-31+G(d,p) level of theory with an SMD description of CH2Cl2. Figure shows the most favorable pathway for halogenating 2e, with the NBn2 portion abbreviated to NMe2, consisting of electrophilic addition (TS-I) followed by deprotonation (TS-II). Calculations showed that outersphere electron transfer processes were inaccessible (DG > 34 kcal mol -1 ) and Figs. S10-S22 provide full computational details of this study.