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

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 13C and 19F NMR spectroscopies. The solid-state molecular structure was determined by X-ray diffraction methods. It crystallizes in the P21/c...

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Bibliographic Details
Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2012-01, Vol.116 (3), p.1110-1118
Main Authors: Hidalgo, A, Avendaño Jiménez, L. P, Ramos, L. A, Mroginski, M. A, Jios, J. L, Ulic, S. E, Echeverría, G. A, Piro, O. E, Castellano, E
Format: Article
Language:English
Subjects:
A: Molecular Structure, Quantum Chemistry, General Theory
Amines - chemistry
Butanones - chemical synthesis
Butanones - chemistry
Crystallography, X-Ray
Ethylamines - chemical synthesis
Ethylamines - chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Quantum Theory
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Spectrum Analysis, Raman
Stereoisomerism
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Summary: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 13C and 19F NMR spectroscopies. 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) 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.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp211536q