Structural and vibrational investigation of 1,2-bis(3,4-dimethoxyphenyl) ethane-1,2-dione (Veratril): experimental and theoretical studies

Abstract

The molecular and crystal structures of 1,2-bis(3,4-dimethoxyphenyl)ethane-1,2-dione (TMBZ = tetramethoxybenzil) were determined by a single-crystal X-ray diffraction, (1)H NMR, and FT-IR spectroscopy. The compound TMBZ (C(18)H(18)O(6), M (r) = 330.32) crystallized in the orthorhombic Fdd2 space group wherein: a = 39.145(4), b = 18.167(2), c = 4.3139(5) angstrom and beta = 90 degrees, Z = 8. The packing of the molecules in the crystal lattice is stabilized by intermolecular C-H center dot center dot center dot O contacts in the herringbone arrangement. The molecular geometry and harmonic frequencies of TMBZ in the ground state were calculated utilizing density functional (B3LYP) method with the 6-311++G(d, p)-basis set. The density functional theory optimized the geometric structure, and vibrational wave numbers of TMBZ in gas phase were compared with the experimental data. A complete assignment of the fundamentals was proposed based on the total energy distribution calculation.