The interactions of acridanes with oxidants were modeled using combined methods of quantum chemistry (DFT B3LYP/6-311G(d,p)), molecular mechanics, MERA model, and MOPS algorithm. The results of simulation are compared with XRD data, oxidation potentials of acridanes, and the reduction potentials of the products of the oxidation reaction. It is shown that elimination of the hydride anion by the reactions of acridanes with oxidants is a consequence of a two-step process; the first step is the transfer of electron density from the HOMO of acridane to the LUMO of the oxidant; the second step is hydrogen elimination from the acridane molecule due to hydrogen bonding with the oxygen atom of the oxidant. The details of the mechanism were established by modeling the acridane-oxidant complexes using the MOPS algorithm including the continuum model of the solvent. The logarithms of the rate constants of the processes depend on the structure parameters of the model complexes with correlation coefficients of at least 0.93.