Spectroscopic, Structural, and Conformational Properties of (Z)-4,4, 4-Trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxypheny1)-2-buten-1-one, C12H12F3NO3: A Trifluoromethyl-Substituted beta-Aminoenone

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, and C-13 and F-19 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) angstrom, b = 7.8210(3) angstrom, c := 13.8970(5) angstrom, beta = 116.162(2)degrees, and Z = 4 molecules per unit cell. The molecule shows a nearly planar molecular skeleton, favored by intramolecular OH center dot center dot center dot 0 and NH center dot center dot center dot 0 bonds, which are arranged in the lattice as an OH center dot center dot center dot 0 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.

Universidad Nacional de La Plata (UNLP)

Universidad Nacional de La Plata (UNLP)

CONICET [PIP 1529]

CONICET

DAAD (Germany)

DAAD-Germany

Departamento de Ciencias Basicas de la Universidad Nacional de Lujan

Departamento de Ciencias Basicas de la Universidad Nacional de Lujan

Deutscher Akademischer Austauschdienst Germany (DAAD)

Deutscher Akademischer Austauschdienst Germany (DAAD)

Facultad de Ingenieria de la Universidad Nacional de La Plata

Facultad de Ingenieria de la Universidad Nacional de La Plata

ANPCyT of Argentina [PME06 2804, PICT06 2315]

ANPCYT of Argentina

FAPESP of Brazil

FAPESP of Brazil