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NBO-Analysis of Peri-dihydroxy-9,10-anthraquinones and their Deprotonated Forms

The natural bonding orbitals (NBO) approach is employed to gain a deeper insight into the nature of intramolecular interactions in a series of peri-hydroxyderivatives of 9,10-anthraquinones and their deprotonated forms. The intuitive predictions of relative energies of these species and the strength of hydrogen bonding were confirmed by the NBO analysis, whereas intuitive evaluation of the role of steric effects in the stability of deprotonated hydroxyanthraquinones seemed to be exaggerated.