Quantum-chemical and correlation study on the tautomerism and ionization of 1,4,5,8-tetrahydroxy-9,10-anthraquinone and its alkyl-substituted derivatives

1,4,5,8-Tetrahydroxy-9,10-anthraquinone and its alkyl derivatives exist as equilibrium mixtures of prototropic tautomers and rotational isomers differing in the mode of intramolecular hydrogen bonding. Their electronic absorption spectra contain πl,π* bands corresponding to 9,10-, 1,10-, 1,4-, and (more rarely) 1,5-anthraquinoid structures. Introduction of substituents, solvation, ionization, and complex formation lead to displacement of tautomeric and conformational equilibria, which are responsible for the observed diversity of their absorption spectra. © 2006 Nauka/ Interperiodica