1,3-Bis(4-chlorophenyl)thiourea

Qin, Yong-Qi; Jian, Fang‐Fang; Liang, Tongling

doi:10.1107/s1600536806040499

Cited by 4 publications

(5 citation statements)

References 1 publication

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“…In between the molecules, the green NCI isosurfaces are found between N-H and ST, indicating the existence of the N-H···ST interaction in all the compounds considered in this study. This result agrees with the findings from the experiments in which NH···ST interaction is important The NCI isosurfaces for the dimer compounds in holding the molecules in the crystal structure [7][8][9][10][11][12][13][14]. Hence, not only can the NH···ST hydrogen bonds hold the thiourea molecules in the solid state [15], it is also responsible for the stability of the thiourea derivatives.…”

Section: Non-covalent Interaction (Nci)supporting

confidence: 90%

“…Generally, the electrophilic and nucleophilic sites between the monomers are interacting with each other, where the NH sites attract the electron-rich ST site. The NCI isosurfaces also exist between the ST and NH of the two monomers, indicating their importance in the interaction of molecules in crystal systems [7][8][9][10][11][12][13][14]. For the dimers, other than the sites where the monomers interact, the individual monomers also show similar reactive sites as in the case of the monomer, as shown in Fig.…”

Section: Electrostatic Potential (Esp)mentioning

confidence: 81%

“…List of the phenyl and arylhalide substituted compounds considered in this study No. Compound Original configuration of the molecules Crystal system Substituent 1 1,3-diphenylthiourea (C13H12N2S1) [7][8] (*) TT orthorhombic Ph-1 CT monoclinic Ph-2 TT orthorhombic Ph-3 TT orthorhombic Ph-4 2 1,3-bis(4-fluorophenyl)thiourea (C13H10F2N2S1) [9] TT orthorhombic Ph-F-p 3 1,3-bis(4-chlorophenyl)thiourea (C13H10N2S1) [10][11] TT orthorhombic Ph-Cl-p-1 TT monoclinic Ph-Cl-p-2 4 1,3-bis(4-bromophenyl)thiourea (C13H10Br2N2S1) [12] TT monoclinic Ph-Br-p…”

Section: ■ Introductionmentioning

confidence: 99%

“…For the compounds considered in this study, those in TT configuration always have the molecules stack in head-totail to form zigzag tapes. It involves twin NH···ST contacts of 2.50 to 2.70 Bohr [7][8][9][10][11][12]14]. The NH···ST contact can be interpreted as hydrogen-bonding interactions to a bifurcated sulphur acceptor.…”

Section: ■ Introductionmentioning

confidence: 99%

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Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Nabil

Ang

2020

Indones. J. Chem.

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The disubstituted thiourea compounds have shown its reliability on their usages in various industries compared to the thiourea compounds. However, they also show capability to exist in different configurations, which would render them to possess different properties and hence affect their usability by unsuspected users. In this study, investigation was carried out on the polymorphism of five disubstituted thiourea compounds in which the phenyl rings and arylhalide acted as substituents. Using the B3LYP/DEF2-TZVP model chemistry with D3-BJ and gCP correctional schemes, the energetic analysis on the possible structural arrangements of the compounds was performed. The topology analysis of non-covalent interaction and electrostatic potential surfaces was used for understanding the interaction and reactivity of the constitute molecules of the compounds. Energetic results show that for all interested compounds, CT and TT configurations may coexist. Between the two types of substituents, phenyl substituted molecules are more flexible with better capability to be nucleophilic compounds. On the other hand, the arylhalide substituted molecules form better electrophilic compounds. The reactive sites of the molecules rotated to the stable new configurations are similar to the molecules in their original configurations observed from experiments.

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Section: Non-covalent Interaction (Nci)supporting

confidence: 90%

Section: Electrostatic Potential (Esp)mentioning

confidence: 81%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Nabil

Ang

2020

Indones. J. Chem.

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“…Structures of substituted thioureas have always been of interest mainly due to the difficulty in obtaining crystals suitable for X-ray analysis [43][44][45][46][47][48][49][50][51][52][53][54][55][56]. Crystals of ligand L partially suitable for X-ray analysis were grown from its chloroform solution by slow evaporation.…”

Section: Resultsmentioning

confidence: 99%

Mononuclear Tricoordinate Copper(I) and Silver(I) Halide Complexes of a Sterically Bulky Thiourea Ligand and a Computational Insight of Their Interaction with Human Insulin

et al. 2022

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Reaction of two equivalents of the bulky 1,3-bis(2,6-diethylphenyl)thiourea ligand (L) with MX (being M = Cu+, Ag+; and X = Cl−, Br−, I−) in acetonitrile afforded neutral complexes of the type [MXL2] [CuClL2].2CH3CN (1a); [CuBrL2].2CH3CN (1b); [CuIL2] (1c): [AgClL2] (2a); [AgBrL2] (2b) and [AgIL2] (2c). The two aromatic groups in free ligand were found to be trans with respect to the thiourea unit, which was a reason to link the ligand molecules via intermolecular hydrogen bonding. Intramolecular hydrogen bonding was observed in all metal complexes. The copper complexes 1a and 1b are acetonitrile solvated and show not only intra- but also intermolecular hydrogen bonding between the coordinated thiourea and the solvated acetonitrile molecules. Silver complexes reported here are the first examples of structurally characterized tricoordinated thiourea-stabilized monomeric silver(I) halides. Molecular docking studies were carried out to analyze the binding modes of the metal complexes inside the active site of the human insulin (HI) protein. Analysis of the docked conformations revealed that the electrostatic and aromatic interactions of the protein N-terminal residues (i.e., Phe and His) may assist in anchoring and stabilizing the metal complexes inside the active site. According to the results of docking studies, the silver complexes exhibited the strongest inhibitory capability against the HI protein, which possesses a deactivating group, directly bonded to silver. All compounds were fully characterized by elemental analysis, NMR spectroscopy, and molecular structures of the ligand, and five out of six metal complexes were also confirmed by single-crystal X-ray diffraction.

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A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents

et al. 2012

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1,3-Bis(4-chlorophenyl)thiourea

Abstract: Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.005 Å Disorder in main residue R factor = 0.061 wR factor = 0.187 Data-to-parameter ratio = 16.4For details of how these key indicators were automatically derived from the article, see

Cited by 4 publications

References 1 publication

Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Mononuclear Tricoordinate Copper(I) and Silver(I) Halide Complexes of a Sterically Bulky Thiourea Ligand and a Computational Insight of Their Interaction with Human Insulin

A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents

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