1-(2-Hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

Abstract

The title compound, C(19)H(20)O(6), crystallizes in the centrosymmetric space group P2(1)/c with one molecule in the asymmetric unit. The molecule is approximately planar and the dihedral angle between the phenyl rings is 11.0 (1) degrees. The H atoms of the central propenone group are trans. There is an intramolecular O-H.O hydrogen bond and the molecules are crosslinked by four intermolecular C-H.O hydrogen bonds, producing a three-dimensional network.

Experimental and quantum chemical studies of a novel synthetic prenylated chalcone

“…On the other hand, the distance between 36O···42O of the prenyl chain and the methoxy group attached to B-ring is 2.766 Å, which determines directly the orientation for methoxy groups. This correlates quite well with the results obtained by the X-Ray diffraction studies reported for similar structures [6]. …”

“…As observed in Table 2, the corresponding geometrical parameters for chalcones 4 [6], 5 [38], 6 [39] and 7 [5] obtained by X-ray diffraction show similar values even though the molecules have different substituents in their structure (See Figure 1). This could indicate that the introduction of diverse functional groups into the aromatic ring system has little effect on specific geometrical parameters (prop-2-en-1-one chain), as reported in previous theoretical and experimental studies [40].…”

“…The results were compared with experimental values reported for geometrical parameters in similar chalcone derivatives. Since the X-ray crystal structure of this novel chalcone has neither been reported nor determined, we decided to use the reported X-ray analyses for similar chalcone derivatives as reference (see Table 2) [5,6,38,39]. The molecular structures of these reference compounds are shown in Figure 1.…”

“…These average values are lower than the reported data for chalcone derivatives, however, they show only a slight discrepancy with the values reported in the literature. The bond distances are: a) 1.375 Å for O – C aromatic , b) 1.421 Å for O – C methyl (both for p- methoxybenzyl 2α - methyl - 2β - [(R) - acetoxy(methoxy)methyl] - 6β - phenoxyacetamidopenam-3α-carboxylate [41]), and c) 1.373 Å for O – C methyl and d) 1.420 Å O – C methyl (for the compound 1-(2-hydroxy-4-methoxyphenyl)-3(2,3,4-trimethoxy-phenyl) prop-2-en-1-one [6]). According to the obtained results, the M06-2X functional in combination with a 6-311++G(d,p) basis set, reproduces experimental geometrical parameters with a good accuracy for bond distances and bond angles in chalcone derivatives.…”

“…In order to obtain information on the nature and expected activities of a given organic compound, it is necessary a better understanding of its spectroscopic properties, as well as the detection of functional groups. Along chemistry community, Nuclear Magnetic Resonance (NMR) is one of the most widely used spectroscopic techniques, and the most sensitive to study organic compounds molecular structure [4-6]. On the other hand, quantum chemical calculations are an important tool for the determination of the relationship between structure and spectral properties [7].…”