Synthesis, crystal X-ray diffraction structure, vibrational properties and quantum chemical calculations on 1-(4-(4-Fluorobenzamido)phenyl)-3-(4-fluorobenzoyl)thiourea (original) (raw)
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Synthesis and Crystal Structure of 1-(3-fluorophenyl)-3-(3,4,5-trimethoxybenzoyl)thiourea
Crystals, 2011
The base catalyzed intramolecular nucleophilic cyclization of 1-(2-bromobenzoyl)-3-(2-fluorophenyl)thiourea (1) in the presence of N,N-dimethyl formamide (DMF) afforded the 1-(3-fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (2) by an intramolecular nucleophilic substitution S N Ar mechanism. The structure was supported by the spectroscopic data and unambiguously confirmed by the single crystal Xray diffraction data. It crystallizes in the orthorhombic space group P na2 1 with unit cell dimensions a = 22.430(4), b = 8.1478(16), c = 13.522(3) Å, V = 2471.2(9) Å 3 . There are two independent molecules per asymmetric unit that are linked to centrosymmetric ABdimers via intermolecular N-H…S bonds.
2017
In the present work, the quantum theoretical calculations of the molecular structure of the 1-(1, 3-Benzothiazol-2-yl)-3-(thiophene-5-carbonyl) thiourea has been predicted and are evaluated using Density Functional Theory (DFT) in gas phase. The geometry of the title compound was optimized by B3LYP/6-311+G and B3LYP/6-311+G* methods and the experimental geometrical parameters of the title compound such as bond lengths (A), bond angles (°) and torsion angels (°) were compared with calculated results. The theoretical 1H and 13C NMR chemical shift (GIAO method) values of the title compound are calculated and compared with the experimental results. The computed data are in good agreement with the experimental data. Frontier molecular orbitals (FMOs) such as HOMO orbital, LUMO orbital and HOMO-LUMO energy gap, molecular electrostatic potential (MEP), electronic properties such as ionization potential, electron affinity, global hardness, electronegativity, electronic chemical potential, e...
Crystal structure of 1-benzoyl-3-(4-fluorophenyl)thiourea
Acta Crystallographica Section E Structure Reports Online, 2014
The title compound, C 14 H 11 FN 2 OS, contains two molecules (A and B) in the asymmetric unit, with different conformations. In molecule A, the dihedral angles between the central thiourea grouping and the phenyl and fluorobenzene rings are 28.77 (8) and 41.82 (8) , respectively, and the dihedral angle between the ring planes is 70.02 (9) . Equivalent data for molecule B are 8.46 (8), 47.78 (8) and 52.99 (9) , respectively. Both molecules feature an intramolecular N-HÁ Á ÁO hydrogen bond, which closes an S(6) ring. In the crystal, A+B dimers linked by pairs of N-HÁ Á ÁS hydrogen bonds generate R 2 2 (8) loops.
Journal of Science and Technology, 2020
Five single molecule methyl substituted Benzoyl pyridinylthiourea compounds namely N-benzoyl-N'-(2-pyridyl)thiourea, N-benzoyl-N'-(6-methyl-2-pyridyl)thiourea, N-benzoyl-N'-(5-methyl-2-pyridyl)thiourea, Nbenzoyl-N'-(4-methyl-2-pyridyl) thiourea and N-benzoyl-N'-(3-methyl-2-pyridyl)thiourea are investigate theoretically for trans-cis and cis-trans conformation at B3LYP 6-31G(d,p) level of theory. Electronic properties have been analyzed by Gaussian 09W package and AIMAll code. Methyl substituent and its position give noticeable effect to reactivity, stabilization, and hydrogen bond interaction strength. AIM prove that 6-methyl substituted on pyridyl ring has significant effect to preferent conformation.
Structural and vibrational study on N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide
Journal of Molecular Structure, 2011
A new thiourea derivative, N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide, is synthesized and characterized by elemental analysis, FTIR, NMR and the single crystal X-ray diffraction study. The title compound crystallizes with two molecules in the asymmetric unit. The dihedral angle between the two aromatic rings in the biphenyl unit is 47.9(2) and 56.52(19)°, respectively, for the two molecules in the asymmetric unit. The molecular conformation is stabilized by intramolecular NAHÁ Á ÁO hydrogen bond. The crystal packing shows that the molecules form centrosymmetric dimers connected by NAHÁ Á ÁS hydrogen bonds. The vibrational properties have been studied by FTIR and FT-Raman spectroscopy along with quantum chemical calculations at the B3LYP/6-311 + G Ã level of approximation. The main normal modes related with the thioamide bands are discussed.
Acta Crystallographica Section E Crystallographic Communications, 2019
In the title tri-substituted thiourea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the molecule [the S—C—N—C torsion angle is −49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hydroxyethyl groups lying to either side of this plane. One hydroxyethyl group is orientated towards the thioamide functionality enabling the formation of an intramolecular N—H...O hydrogen bond leading to anS(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the molecule is twisted. The experimental molecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the molecular packing, hydroxyl-O—H...O(hydroxyl) and hydroxyl-O—H...S(thione) hydrogen bonds lead to the formation of a supramolecular layer in theabplane; no directional interactions are found between layers. The influence of the specified supramole...
Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naph thoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C@O and C@S adopting a pseudo-antiperiplanar conformation. An intramolecular NAH O@C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular NAH S@C and NAH O@C hydrogen-bonding interactions involving the acylthiourea moiety. Compound 2 is further stabilized by p-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV–Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.
European Journal of Chemistry, 2010
An efficient synthesis of the title compound, 1-(4-methylbenzoyl)-3-(4-aminosulfonyl phenyl)thiourea, was carried out by reaction of 4-methylbenzoyl chloride with potassium thiocyanate in acetone to afford 4-methylbenzoyl isothiocyanate in situ followed by treatment with sulfanilamide. The structure was confirmed by spectroscopic data and elemental analyses. The molecular structure was determined from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P21/n with unit cell dimensions of a = 4.8116 Å, b = 17.150(3) Å, c = 18.677(3) Å, = 96.487(4) °, and V = 1531.4(5) Å 3 .
Journal of the Brazilian Chemical Society, 2018
A thiourea derivative, N-[(phenylcarbonyl)carbamothioyl]benzamide, was synthesized and characterized by elemental analysis, thermal analysis, spectroscopic methods (Fourier transform infrared (FTIR), UV-Vis, Raman, matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI-TOF), tandem mass spectrometry (MS/MS) and nuclear magnetic resonance (NMR)) and quantum-chemical calculations. The synthetic route was simple and efficient, conducted just by one-step and no purification step was needed. The compound crystallizes in a non-centrosymmetric orthorhombic crystal system with a P2 1 2 1 2 1 space group, with a = 5.06220(10) Å, b = 11.8623(3) Å, c = 21.9682(8) Å. The molecular conformation of the solid is stabilized by the N-H•••O intramolecular hydrogen bond, which was present in the X-ray structure and was also found in the optimized geometry. The theoretical analysis showed that this strong interaction remains even when molecules are solvated, i.e., the rotation barrier and the hydrogen bond strength are greater than the solvent stabilization energy. In addition to this hydrogen bond effect, the relative position of phenyl groups has a certain influence on the chemical behavior of this thiourea and probably for other phenylthioureas.