title: 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 β-aminoenone.
abstract: 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.
authors.affiliation: CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, República Argentina.
authors.forename: A
authors.initials: A
authors.lastname: Hidalgo
authors.forename: L P Avendaño
authors.initials: LP
authors.lastname: Jiménez
authors.forename: L A
authors.initials: LA
authors.lastname: Ramos
authors.forename: M A
authors.initials: MA
authors.lastname: Mroginski
authors.forename: J L
authors.initials: JL
authors.lastname: Jios
authors.forename: S E
authors.initials: SE
authors.lastname: Ulic
authors.forename: G A
authors.initials: GA
authors.lastname: Echeverría
authors.forename: O E
authors.initials: OE
authors.lastname: Piro
authors.forename: E
authors.initials: E
authors.lastname: Castellano
mesh_terms: D000588:Amines / Q000737:chemistry*; D002074:Butanones / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005021:Ethylamines / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013059:Spectrum Analysis, Raman; D013237:Stereoisomerism
chemical_list: C572110:(Z)-4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxyphenyl)-2-buten-1-one; D000588:Amines; D002074:Butanones; D005021:Ethylamines