1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea

Rauf, M. Khawar; Bolte, Michael; Rauf, Abdur

doi:10.1107/s1600536808043444

Cited by 4 publications

(1 citation statement)

References 7 publications

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“…The C-N bond distances [C1-N1 = 1.395 (2) Å, C9-N1 = 1.396 (2) Å and C9-N2 = 1.344 (2) Å] observed in the title compound are consistent with those reported for the other thiourea derivatives (1-(3-chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea (Khawar Rauf et al, 2009d), 1-(3-chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea (Khawar Rauf et al, 2009c), 1-(2,6-dichlorobenzoyl)-3-(2,3,5,6-tetrachlorophenyl)thiourea (Khawar Rauf et al, 2009a), suggesting a partial double-bond character.…”

Section: Data Collectionsupporting

confidence: 84%

N-(Diphenylcarbamothioyl)-3-methylbenzamide

Binzet¹,

Flörke²,

Külcü³

et al. 2009

Acta Cryst E

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The synthesis of the title compound, C21H18N2OS, involves the reaction of 3-methylbenzoyl chloride with potassium thiocyanate in dry acetone followed by condensation of the 3-methylbenzoyl isothiocyanate with diphenylamine. The carbonyl [C—O = 1.215 (2) Å] and thiocarbonyl [C—S = 1.6721 (17) Å] distances indicate that these correspond to double bonds. The short C—N bonds at the center of the molecule reveal the effects of resonance in this part of the molecule. The conformation of the molecule with respect to the thiocarbonyl and carbonyl groups is twisted. The 3-methylphenyl and two phenyl rings are also twisted, with dihedral angles of 75.67 (9) and 14.91 (9)°. The phenyl rings are rotated out of the mean plane of the N—C—S—N atoms by 66.87 (8) and 78.40 (9)°. Pairs of molecules are linked into centrosymmetric dimers via intermolecular N—H⋯S interactions and a C—H⋯O link also occurs. The dimers are stacked along the a axis.

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Section: Data Collectionsupporting

confidence: 84%

N-(Diphenylcarbamothioyl)-3-methylbenzamide

Binzet¹,

Flörke²,

Külcü³

et al. 2009

Acta Cryst E

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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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4-Bromo-N-(diethylcarbamothioyl)benzamide

et al. 2009

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The synthesis of the title compound, C12H15BrN2OS, involves the reaction of 4-bromobenzoyl chloride with potassium thiocyanate in dry acetone, followed by condensation of 4-bromobenzoyl isothiocyanate with diethylamine. The carbonyl and thiocarbonyl bond lengths indicate that these correspond to double bonds. The short C—N bond lengths reveal the effects of resonance in this part of the molecule. The conformation of the molecule with respect to the thiocarbonyl and carbonyl units is twisted, with torsion angles of −5.7 (3) and 87.2 (2)°. The N atom of the diethylamine group is sp 2-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and − antiperiplanar conformations with angles of −179.89 and 179.92°. In the crystal structure, the molecules form infinite chains via an intermolecular N—H⋯O interaction.

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1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea

Cited by 4 publications

References 7 publications

N-(Diphenylcarbamothioyl)-3-methylbenzamide

N-(Diphenylcarbamothioyl)-3-methylbenzamide

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

4-Bromo-N-(diethylcarbamothioyl)benzamide

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