1962 Volume 35 Issue 7 Pages 1060-1063
The basicities of the nitro-substituted benzoanthrones were measured. One nitro-substitution decreases the basicity of beazoanthrone by about two pK units, as in the case of nitrosubstituted aniline and anthraquinone. This is explained qualitatively not by the inductive effect but by the resonance effect of the nitro groups on the carbonyl group of benzoanthrone in such way as to estimate approximately the change of resonance energies in the cases of both hydrocarbons and their related quinones. The gradient of the straight line of pK plotted versus log(N∗N) in the case of nitro-substitution is greater than in the case of chlorosubstitution. This means that the contribution of the polarized structure in the ground state to resonance effect is greater in the case of the nitro-derivatives of benzoanthrone than in the case of the chloro-derivatives.
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