Half-wave potentials and LCAO-SCF-MO calculations for carcinogenic benz[c]acridines.

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Abstract
Half-wave reduction potential and half-peak oxidation potential were measured for 11 methyl-substituted benz[c]acridines and unsubstituted benz[c]acridine in acetonitrile with tetraethylammonium perchlorate electrolyte. A linear correlation was obtained between the energy of the lowest unoccupied molecular orbital calculated by LCAO-SCF [linear combination of atomic orbital-self consistent field] method and the half-wave reduction potential, and between the energy of the highest occupied molecular orbital and the half-peak oxidation potential. The correlations between carcinogenic activity and both half-wave oxidation and reduction potentials were interpreted in connection with the electron charge density of the K-region. The results of LCAO-SCF calculation for the electron charge density and the electrophilic superdelocalizability index indicated that the electrophilic reactivity of the K-region or the ring nitrogen atom of methyl-substituted benz[c]acridines may be essential for their carcinogenic activity.

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