4-Chloro-<i>N</i>-[<i>N</i>-(6-methyl-2-pyridyl)carbamothioyl]benzamide

Binzet, Gün; Emen, Fatih Mehmet; Flörke, Ülrich; Yeşilkaynak, Tuncay; Külcü, Nevzat; Arslan, Hakan

doi:10.1107/s1600536808041123

Cited by 21 publications

(11 citation statements)

References 21 publications

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“…Other D−H···A patterns are also known, with N−H···O, N−H···S and/or C−H···O forming infinite chains, [145] two-dimensional sheets [124] or three-dimensional networks with a combination of dimers and chains. [135] Bifurcated N−H hydrogen bonds are also usually observed, [65,216,225] the N−H group forming both an intramolecular and intermolecular N−H···O hydrogen bond.…”

Section: X-ray Crystal Packingmentioning

confidence: 98%

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

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186

118

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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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Section: X-ray Crystal Packingmentioning

confidence: 98%

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

Self Cite

186

118

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“…Over the past couple of years we have been focusing on the preparation and characterization of new carboxamides which are bonded with a thiourea group [1,2,3,4,5,25,26,27,28,29,30,31,32]. Taking into consideration all the features described above, we focused our efforts in the present work on the synthesis of carboxamide derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

et al. 2009

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A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl and naphthalen-1yl) have been synthesized. The compounds obtained were characterized by elemental analyses, IR spectroscopy and 1H-NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H2L9, was also characterized by a single crystal X-ray diffraction study. This compound, C18H20N2OS, crystallizes in the triclinic space group Pī, with Z = 2, and unit cell parameters a = 6.9921(14) Å, b = 11.002(2) Å, c = 12.381(3) Å, α = 113.28(3)°, β = 99.38(3)°, and γ = 101.85(3)°. The cyclohexane ring adopts a chair conformation. The molecular conformation of the compound is stabilized by an intramolecular (N2-H2•••O1) hydrogen bond which forms a pseudo-six-membered ring.

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“…Benzoylthiourea derivatives are considered privileged compounds, because of their simple preparation with high yields [1][2][3][4][5][6][7]. The synthesis of new benzoylthiourea compounds also becomes widespread due to their potential application in biological [8][9][10][11][12] and analytical chemistry [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Cyclic Voltammetric Studies on the Metal Complexes of N-(Dimethylcarbamothioyl)-4-fluorobenzamide

Binzet

Turunç

Flörke

et al. 2018

Journal of Chemistry

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We synthesized N-(dimethylcarbamothioyl)-4-fluorobenzamide compound and its copper(II) and nickel(II) complexes. The structures of compounds have been characterized by elemental analysis and spectral data (IR, 1 H NMR). Furthermore, crystal and molecular structure of the synthesized complexes have been identified by using single crystal X-ray diffraction data. In the complexes formation the metal atom was coordinated via two sulfur atoms and two oxygen atoms. The single crystal structure of copper(II) and nickel(II) complex exhibits slightly distorted square planar geometry. The oxygen atoms are in a cis configuration. It appeared that the lengths of the thiocarbonyl and carbonyl bonds are longer than the average for C=S and C=O; meanwhile the C-N bonds in the complex ring appeared to be shorter than the average for C-N single bonds. These data show that C-O, C-S, and C-N bond lengths of the complexes suggest considerable electronic delocalization in the chelate ring. All bond lengths and angles obtained as a result of the analyses are found to be within experimental error limits. The obtained crystal analysis data shows that the structure of complex compounds is compatible with similar compounds in literature. Electrochemical behavior of complexes has been investigated by cyclic voltammetry technique in aprotic media. From the cyclic voltammetric investigation, both of the complexes have demonstrated electroactive properties.

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4-Chloro-N-[N-(6-methyl-2-pyridyl)carbamothioyl]benzamide

Cited by 21 publications

References 21 publications

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

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

Synthesis and Characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide Derivatives: The Crystal Structure of N-(Naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide

Crystal Structure and Cyclic Voltammetric Studies on the Metal Complexes of N-(Dimethylcarbamothioyl)-4-fluorobenzamide

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