Facile Synthesis and Characterization of Symmetric N-[(Phenylcarbonyl) carbamothioyl]benzamide Thiourea: Experimental and Theoretical Investigations (original) (raw)
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Journal of Molecular Structure, 2010
The 1-(4-(4-Fluorobenzamido)phenyl)-3-(4-fluorobenzoyl)thiourea species (1) has been synthesized and characterized by GC-MS, elemental analyses and 1 H NMR and FTIR spectroscopy techniques. The crystal structure of the novel compound -having a benzamide moiety attached to a thiourea nucleus -has been determined by X-ray diffraction. The species crystallize in the triclinic space group P-1, Z = 4, with 2 molecules per asymmetric unit. Additionally there is one ethylacetate solvent molecule per asymmetric unit. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is mutually antiperiplanar. Density functional theory methods have been applied to determine the conformational space around the central -C(O)NHC(S)NH-moiety. 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.
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 .
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.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015
The vibrational analysis (FT-IR and FT-Raman) for the new 1-(2chlorobenzoyl)thiourea species suggests that strong intramolecular interactions affect the conformational properties. The X-ray structure determination corroborates that an intramolecular N-H•••O=C hydrogen bond occurs between the carbonyl (-C=O) and thioamide (-NH 2) groups. Moreover, periodic system electron density and topological analysis have been applied to characterize the intermolecular interactions in the crystal. Extended N-H•••S=C hydrogen-bonding networks between both the thioamide (N-H) and carbamide (NH 2) groups and the thiocabonyl bond (C=S) determine the crystal packing. The Natural Bond Orbital population analysis demonstrates that strong hyperconjugative remote interactions are responsible for both, intra and intermolecular interactions. The Atom in Molecule (AIM) results also show that the N-H•••Cl intramolecular hydrogen bond between the 2-Cl-phenyl ring and the amide group characterized in the free molecule changes to an N•••Cl interaction as a consequence of crystal packing.
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...
Synthesis and single crystal structure analysis of three novel benzoylthiourea derivatives
Turkish Journal of Chemistry, 2009
N,N-dimethyl-N' -(2-methylbenzoyl)thiourea, C11H14N2SO (HL1), N,N-dibutyl-N' -(2-methylben\-zoyl)thiourea, C{17}H{26}N2SO (HL2), and N,N-dihexyl-N' -(2-methylbenzoyl) thiourea, C{21}H{34}N2SO (HL3) were synthesized and characterized by elemental analysis, spectroscopic methods (FT-IR, NMR), and single crystal X-ray diffraction. Compound HL1 crystallizes in the monoclinic system, space group P21/c, Z = 4. Compound HL3 also crystallizes in the monoclinic system, space group P21/n, Z = 8 with 2 independent molecules in the asymmetric unit. Compound HL2 crystallizes in the orthorhombic system, space group Pcnn, Z = 8. In all compounds, molecules form dimers through the strong intermolecular N-H...S hydrogen bonds. Moreover, there are different types of intra- and inter-molecular interactions in the crystal structures, and so the molecules of the 3 compounds also pack differently.
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.
Chemical Physics, 2014
The synthesis of a novel 1-acyl-thiourea species (C 14 H 17 N 2 O 2 SCl), has been tailored in such a way that two distinct NAHÁ Á ÁO@C intramolecular competing hydrogen bonds are feasible. The X-ray structure analysis as well as the vibrational (FT-IR and FT-Raman) data reveal that the S conformation is preferred, with the C@O and C@S bonds of the acyl-thiourea group pointing in opposite directions. The preference for the intramolecular NAHÁ Á ÁO@C hydrogen bond within the AC(O)NHC(S)NHA core is confirmed. The Natural Bond Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO ? r ⁄ (NAH) remote interaction between the acyl and the thioamide NAH groups is responsible for the stabilization of the S conformation. Intermolecular interactions have been characterized in the periodic system electron density and the topological analysis reveals the presence of an extended intermolecular network in the crystal, including a ClÁ Á ÁN interaction playing a relevant role in crystal packing.