Spectroscopic, structural and conformational properties of (Z)-4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxyphenyl)-2-Buten-1-one, C12H12F3NO3: a trifluoromethyl substituted beta-Aminoenone

A. HIDALGO; L. AVENDAÑO JIMÉNEZ; L. RAMOS; M. MROGINSKI; J. L. JIOS; S. ULIC; G. ECHEVERRÍA; O. E. PIRO; E. E. CASTELLANO

JOURNAL OF PHYSICAL CHEMISTRY A

AMER CHEMICAL SOC

Año: 2012 vol. 116 p. 1110 - 1118

1089-5639

The (Z)-4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxyphenyl)-2-buten-1-one (C12H12F3NO3) compound was thoroughly studied by IR, Raman, UV-visible, 13C and 19F NMR spectroscopy. The solid state molecular structure was determined by X-ray diffraction methods. It crystallizes in the P21/c space group with a=12.1420(4), b=7.8210(3), c=13.8970(5) Å, b=116.162(2)°, and Z=4 molecules per unit cell. The molecule shows a nearly planar molecular skeleton, favored by intra-molecular OH···O and NH···O bonds, which are arranged in the lattice as an OH···O bonded polymer coiled around crystallographic two-fold screw-axes. The three postulated tautomers were evaluated using quantum chemical calculations. The lowest energy tautomer (I) calculated with DFT methods agrees with the observed crystal structure. The structural and conformational properties are discussed considering the effect of the intra- and inter-molecular hydrogen bond interactions.