Synthesis, structural elucidation and DFT studies of ortho-hydroxy acetophenones

Two ortho-hydroxy acetophenones, namely 2,6-dihydroxy-4-methyl acetophenone [C9H10O3] (1) and 2,4-dihydroxy-3-acetyl-6-methyl acetophenone [C11H12O4] (2) have been synthesized and characterized by spectroscopic and X-ray structural studies. Compound (1) crystallizes in monoclinic system, space group P21/c, with a = 3.888(3) Å, b = 26.974(17) Å, c = 14.940(9) Å, β = 91.919(8)°, Z = 8, whereas compound (2) crystallizes in orthorhombic system, space group Pbca, with a = 7.255(2) Å, b = 14.410(4) Å, c = 18.332(1) Å, Z = 8. The crystal packing of (1) exhibits intermolecular O–H···O hydrogen bonds forming a parallel chain propagating along (0 1 0) direction, whereas in (2), the combination of intermolecular C–H···O hydrogen bonds and π–π interactions generate a two-dimensional network. The molecular geometries and electronic structure of (1) and (2) were calculated at the DFT level using the hybrid exchange correlation functional, BLYP, PW91, PBE and BP.