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) Å and b = 90°, Z = 8. The packing of the molecules in the crystal lattice is stabilized by intermolecular C-H_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.

Comprehensive Understanding of Structure- Photosensitivity Relationships of Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimers

“…pseudogem -DPI-TMDPI[2.2]PC ( 4 ) and pseudogem -TMDPI-DPI[2.2]PC ( 5 ) were synthesized according to Scheme , using pseudogem -[4-formyl-13-(4,5-diphenyl-1 H -imidazol-2-yl)][2.2]paracyclophane as a starting material. Pseudogem -[4-formyl-13-(4,5-diphenyl-1 H -imidazol-2-yl)][2.2]paracyclophane ( 1 ) and 3,3′,4,4′-Tetramethoxybenzil ( 2 ) were prepared according to a literature procedure.…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

“…Due to interesting optical properties of benzil derivatives, Sengul et al [166] synthesized 1,2-bis(3,4-dimethoxyphenyl)ethane-1,2-dione (a species also known as Veratril, TMBZ and tetramethoxybenzil). X-ray diffraction and infrared spectra were investigated.…”