Two 2-trifluoromethylchromones, 6-nitro-2-trifluoromethylchromone (1) and 6-amino-2-trifluoromethylchromone (2) were synthesized and characterized by NMR ((1)H, (13)C, and (19)F), UV-vis, vibrational (IR and Raman) spectroscopy, MS spectrometry, and compound 1 also by single structural X-ray diffraction methods. This substance crystallizes in the monoclinic P2(1)/c space group with Z = 4 molecules per unit cell. In the solid, the fused rings and the amino group of 1 are coplanar and the trifluoromethyl group adopts a nearly staggered conformation. The NMR, vibrational, and electronic spectra were discussed and assigned with the assistance of DFT calculations.
The (Z)-4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxyphenyl)-2-buten-1-one (C(12)H(12)F(3)NO(3)) compound was thoroughly studied by IR, Raman, UV-visible, and (13)C and (19)F NMR spectroscopies. The solid-state molecular structure was determined by X-ray diffraction methods. It crystallizes in the P2(1)/c space group with a = 12.1420(4) Å, b = 7.8210(3) Å, c = 13.8970(5) Å, β = 116.162(2)°, and Z = 4 molecules per unit cell. The molecule shows a nearly planar molecular skeleton, favored by intramolecular OH···O and NH···O bonds, which are arranged in the lattice as an OH···O bonded polymer coiled around crystallographic 2-fold screw-axes. The three postulated tautomers were evaluated using quantum chemical calculations. The lowest energy tautomer (I) calculated with density functional theory methods agrees with the observed crystal structure. The structural and conformational properties are discussed considering the effect of the intra- and intermolecular hydrogen bond interactions.
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