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

Štrukil, Vjekoslav; Igrc, Marina Diana; Fábián, László; Eckert‐Maksić, Mirjana; Childs, Scott L.; Reid, David G.; Duer, Melinda J.; Halász, Ivan; Mottillo, Cristina; Friščić, Tomislav

doi:10.1039/c2gc35799b

Cited by 85 publications

(57 citation statements)

References 156 publications

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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%

“…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: ■ 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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“…Compound 24 was prepared from compound 22 coupled with 1‐pyrenebutyric acid by using EDC ⋅ HCl, HOBt and DMAP and compound 25 was prepared from compound 22 coupled with 1‐naphthyl isocyanate in acetonitrile. The following receptors were synthesised as described in literature: 26 ,31 27 ,32 28 ,33 29 ,16 30 ,17 31 12 and 32 – 47 14. 15…”

Section: Methodsmentioning

confidence: 99%

Towards the Discrimination of Carboxylates by Hydrogen‐Bond Donor Anion Receptors

Kadam

Martin

Haav

et al. 2015

Chemistry A European J

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The binding constants (log Kass ) of small synthetic receptor molecules based on indolocarbazole, carbazole, indole, urea and some others, as well as their combinations were measured for small carboxylate anions of different basicity, hydrophilicity and steric demands, that is, trimethylacetate, acetate, benzoate and lactate, in 0.5 % H2 O/[D6 ]DMSO by using the relative NMR-based measurement method. As a result, four separate binding affinity scales (ladders) including thirty-eight receptors were obtained with the scales anchored to indolocarbazole. The results indicate that the binding strength is largely, but not fully, determined by the strength of the primary hydrogen-bonding interaction. The latter in turn is largely determined by the basicity of the anion. The higher is the basicity of the anion the stronger in general is the binding, leading to the approximate order of increasing binding strength, lactate

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“…It was due to the presence of more active sites of thiourea moieties containing C=S, C=O, and N-H groups, which are easily protonated under acidic condition and interacted with the carboxyl and phosphate groups of the bacterial surfaces, thus enhancing the biological activities [7]. Various methods have been reported to make this versatile group of thiourea derivatives easily accessible with excellent yields [2,[9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Ngaini

Zulkiplee

Halim

2017

Journal of Chemistry

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In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

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

Cited by 85 publications

References 156 publications

Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Conformational and Topology Analysis of Diphenylthiourea and Diarylhalidethiourea Compounds Using DFT

Towards the Discrimination of Carboxylates by Hydrogen‐Bond Donor Anion Receptors

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

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