S. Gupta, C. Anjana, N. Sen
Jul 6, 2012
Citations
1
Influential Citations
6
Citations
Journal
Journal of Chemical Crystallography
Abstract
The title compound C24H22O3, [common name: 4-tert-butyl-2,6-dibenzoylphenol (bdbpH)] (I), crystallizes in the orthorhombic space group P2(1)2(1)2(1) with unit cell parameters a = 7.7633(3), b = 11.4457(6) and c = 21.5319(8) Å, α = β = γ = 90º, Z = 4. In the crystal structure of I, the dihedral angles between the mean planes of the central phenyl ring and the two benzene rings are 71.3(1)° and 44.9(7)°. The two benzene rings are not coplanar with dihedral angles of 42.6(7)° between them. An intramolecular O–H···O hydrogen bond is observed in the asymmetric unit. The crystal packing is stabilized by weak intermolecular C–H···O interactions. Comparison of the optimized geometries by means of a density functional theory molecular orbital theoretical calculation at the B3LYP/6-31g(d) level with the corresponding crystal structures gives support to these observations. The electronic spectra of I and 4-methyl-2,6-dibenzoylphenol (mdbpH) also predicted by the B3LYP/6-31g(d) method show some blue shifts compared with their experimental data.Graphical AbstractThere are significant changes in corresponding bond lengths and angles and crystal packing of phenol-based diketones having OH, CH3 or C(CH3)3 substituents in the para-position. Density functional theory (DFT) molecular orbital calculations have reproduced the structures of 4-methyl-2,6-dibenzoylphenol (mdbpH) and 4-tert-butyl-2,6-dibenzoylphenol (bdbpH, I) on the whole. The electronic spectra predicted by DFT MO calculations show some blue shifts compared with their experimental data.