Structural and spectroscopic study on N-2-fluorobenzoyl-N′-4-methoxyphenylthiourea

Yang, Wen; Zhou, Wei; Zhang, Zhengjiang

doi:10.1016/j.molstruc.2006.05.033

Cited by 58 publications

(21 citation statements)

References 22 publications

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“…The C7-N1, N2-C8, C7-N2, N4-C22, N4-C21, and N3-C21 bond lengths are 1.339(5), 1.325(5), 1.341(5), 1.315(5), 1.340(5) and 1.342(4) Å, respectively, and these bond lengths are shorther than the normal C-N single bond (1.48 Å) and longer than normal C=N double bond (1.25 Å) [28]. But N1-C4, N1-C1, N3-C15 and N3-C18 bond lengths are 1.467(5), 1.485(5), 1.473(4) and 1.478(4) Å, respectively, and these bond distance are similar to the normal C-N single bond [29][30][31][32][33][34][35][36].…”

Section: Resultsmentioning

confidence: 76%

Crystal structure of cis-copper(II) complex with N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligand

et al. 2016

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Copper(II) complex, cis-[Cu(L-κ 2 S,O)2] of N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligands (HL) has been synthesized and structurally characterized by various spectroscopic techniques and single crystal X-ray diffraction crystallography. The cis-[Cu(L-κ 2 S,O)2], C28H50CuN4O2S2: Monoclinic, space group P21/n (no. 14), a = 10.025(2) Å, b = 21.724(4) Å, c = 14.848(3) Å, β = 100.60(3)°, Z = 4, Dcalc = 1.259 g/cm 3 , 22069 reflections measured (5.88° ≤ 2Θ ≤ 50.2°), 5639 unique (Rint = 0.0630, Rsigma = 0.0678) which were used in all calculations. The final R1 was 0.0488 (≥2σ(I)) and wR2 was 0.1277 (all data). Single crystal analysis revealed that a square-planar coordination geometry is formed around the copper atom by two sulphur and two oxygen atoms of the related ligand, which are in a cis configuration. KEYWORDS Thioureas Cis-complexCopper complex Single crystal structure Carboxamide derivatives Cyclohexanecarboxamide Cite this: Eur.

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Section: Resultsmentioning

confidence: 76%

Crystal structure of cis-copper(II) complex with N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligand

et al. 2016

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“…Finally, the m(C@S) stretching mode (thioamide band IV) of 1-acylthiourea compounds is found around in the 600-800 cm À1 range [3,4,59,60], but higher wavenumbers values (up to 1100 cm À1 ), are also reported [44,48]. These differences suggest that the m(C@S) stretching mode is very sensitive to the presence of an intermolecular interactions involving the C@S group [41], which originates an intense Raman dispersion due to the polarizability of the C@S bond [61].…”

Section: Vibrational Analysismentioning

confidence: 94%

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed

Ashraf

White

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-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 N-H⋯O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular N-H⋯S=C and N-H⋯O=C hydrogen-bonding interactions involving the acylthiourea moiety. Compound 2 is further stabilized by π-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.

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“…Zhou and coworkers [147] reported the infrared spectrum of solid 1-(2-fluorobenzoyl)-3-(4-methoxyphenyl) thiourea, where a weak band appearing at 2438 cm −1 could be assigned to the ν(S−H) stretching mode. Aydin et al [143] suggested that tautomeric equilibrium exists in 4-(3-benzoylthioureido)benzoic acid, promoted by a intramolecular proton shifts between the thioketo-sulfur and the amine-nitrogen, via intramolecular hydrogen bonding N−H···S or S−H···N.…”

Section: Thione-thiol Tautomerismmentioning

confidence: 99%

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

198

123

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This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R 1 C(O)N (1) HC(S)N (3) R 2 R 3 . In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra-and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono-and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure-activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.

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Structural and spectroscopic study on N-2-fluorobenzoyl-N′-4-methoxyphenylthiourea

Cited by 58 publications

References 22 publications

Crystal structure of cis-copper(II) complex with N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligand

Crystal structure of cis-copper(II) complex with N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide ligand

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

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