Synthesis and exploration of configurational dynamics in equilibrating<i>E</i>/<i>Z</i>2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

Singh, Rahul; Kumar, Parvin; Sindhu, Jayant; Devi, Meena

doi:10.1039/d1nj06109g

Cited by 7 publications

(4 citation statements)

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“…It is industrially produced by inducing a chemically similar substance like ammonium thiocyanate (NH 4 SCN) to undergo rearrangement. 11 It can also be produced by the reaction between hydrogen sulfide and calcium cyanamide (CaCN) in the presence of carbon dioxide (CO 2 ). 12 Despite the poisonous characteristics of thiourea, its derivatives prove to be useful in drug delivery.…”

Section: Introductionmentioning

confidence: 99%

“…However, thiourea tends to form colorless crystals at the temperature of 182 °C (860 °F). It is industrially produced by inducing a chemically similar substance like ammonium thiocyanate (NH 4 SCN) to undergo rearrangement . It can also be produced by the reaction between hydrogen sulfide and calcium cyanamide (CaCN) in the presence of carbon dioxide (CO 2 ) .…”

Section: Introductionmentioning

confidence: 99%

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RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

et al. 2022

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Upon various investigations conducted in search for a nanosensor material with the best sensing performance, the need to explore these materials cannot be overemphasized as materials associated with best sensing attributes are of vast interest to researchers. Hence, there is a need to investigate the adsorption performances of various metal-doped fullerene surfaces: C 59 Au, C 59 Hf, C 59 Hg, C 59 Ir, C 59 Os, C 59 Pt, C 59 Re, and C 59 W on thiourea [SC(NH 2 ) 2 ] molecule using first-principles density functional theory computation. Comparative adsorption study has been carried out on various adsorption models of four functionals, M06-2X, M062X-D3, PBE0-D3, and ωB97XD, and two double-hybrid (DH) functionals, DSDPBEP86 and PBE0DH, as reference at Gen/def2svp/LanL2DZ. The visual study of weak interactions such as quantum theory of atoms in molecule analysis and noncovalent interaction analysis has been invoked to ascertain these results, and hence we arrived at a conclusive scientific report. In all cases, the weak adsorption observed is best described as physisorption phenomena, and CH 4 N 2 S@C 59 Pt complex exhibits better sensing attributes than its studied counterparts in the interactions between thiourea molecule and transition metal-doped fullerene surfaces. Also, in the comparative adsorption study, DH density functionals show better performance in estimating the adsorption energies due to their reduced mean absolute deviation (MAD) and root-mean-square deviation (RMSD) values of (MAD = 1.0305, RMSD = 1.6277) and (MAD = 0.9965, RMSD = 1.6101) in DSDPBEP86 and PBE0DH, respectively.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

et al. 2022

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“…In our previous investigation, we observed that 2-aryliminothiazolidinone derivatives exhibited dynamic behaviour and computed the kinetic and thermodynamic parameters of the dynamic chemical system with the help of the combined use of the coalescence temperature method and extensive peak shape analysis 44 (Fig. 2).…”

Section: Data Setmentioning

confidence: 99%

“…The experimental data of Δ G ‡ for the dynamic system was obtained from our previous investigation (Fig. 1) 44 and constitutes the endpoint for the development of CORAL QSGFEAR models. The predictive potential of the developed model is estimated with the correlation intensity index (CII), a new criterion to improve the predictive reliability of the developed model.…”

Section: Introductionmentioning

confidence: 99%

Monte Carlo based QSGFEAR: prediction of Gibb's free energy of activation at different temperatures using SMILES based descriptors

et al. 2022

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Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives

Phaenok,

Nguyen,

Soorukram

et al. 2023

Chemistry A European J

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Thiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive and readily available feedstocks are scarce. In this article, we disclose the synthesis of these motifs using elemental sulfur and nitromethane as the starting materials. The method harnesses the multi‐electron auto‐redox property of nitromethane in the presence of sulfur and amines, delivering thiourea products without any added oxidant or reductant. Extension of this reaction to cyclizable amines and/or higher homologues of nitromethane led to a wide range of nitrogen heterocycles and thioamides. Operationally simple, the reactions are scalable, tolerate a wide range of functional groups, and can be employed for the direct functionalization of natural products. Mechanistically, the nitro group was found to act as an oxidant leaving group, being reduced to ammonia whereas sulfur, along with the role of a sulfur building block for the thiocarbonyl group, behaved as a complementary reductant, being oxidized to sulfate.

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Synthesis and exploration of configurational dynamics in equilibratingE/Z2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

Abstract: In the present manuscript, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR...

Cited by 7 publications

References 35 publications

RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

Monte Carlo based QSGFEAR: prediction of Gibb's free energy of activation at different temperatures using SMILES based descriptors

Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives

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Synthesis and exploration of configurational dynamics in equilibratingE/Z2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

Abstract: In the present manuscript, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR...

Cited by 7 publications

References 35 publications

RETRACTED: Probing the Reactions of Thiourea (CH4N2S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C59X)

RETRACTED: Probing the Reactions of Thiourea (CH4N2S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C59X)

Monte Carlo based QSGFEAR: prediction of Gibb's free energy of activation at different temperatures using SMILES based descriptors

Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives

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RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)

RETRACTED: Probing the Reactions of Thiourea (CH₄N₂S) with Metals (X = Au, Hf, Hg, Ir, Os, W, Pt, and Re) Anchored on Fullerene Surfaces (C₅₉X)