Effect of Substitution of Hydrogen Atoms in the Molecules of Anthrone and Anthraquinone

The geometry of anthrone and anthraquinone—natural substances of plant origin—was investigated under the substitution of hydrogen atoms in side aromatic ring and, for anthrone, also in the central ring. A significant influence of substitution on geometry expressed by the angle between the side rings was shown. The geometry changes are connected with the changes of electron density and aromaticity of the anthrone and anthraquinone rings. The flexibility of the investigated compounds was confirmed by comparison of the optimized molecules and the molecules in the crystal state where the packing forces can influence the molecular geometry.