Tautomerism of the natural anthraquinones physcion and emodin and their analogs

The 9,10-1,10-anthraquinoid tautomer was found to be characteristic of physcion and emodin and their analogs in solutions using spectrophotometric, quantum-chemical, and correlation methods. Ionization of these compounds was accompanied by a shift in tautomeric equilibrium. In alkaline solutions 1,10-anthraquinoid anions with a single α-hydroxy that were stabilized by an intramolecular H-bond were formed. Tautomerism occurred in both the ground and excited states of the molecules. ©2005 Springer Science+Business Media, Inc.