Group 10 metal complexes with a tetradentate thiosemicarbazonate ligand: Synthesis, crystal structures and computational insights into the catalysis for C–C coupling via Mizoroki-Heck reaction

Lima, Jackelinne Camargo; Nascimento, Rebecca D.; Vilarinho, Luana M.; Borges, Alice P.; Silva, Leonardo H. F.; Souza, Jhonathan R.; Dinelli, Luís R.; Deflon, Victor M.; Machado, Antônio Eduardo da Hora; Bogado, André L.; Maia, Pedro Ivo da Silva

doi:10.1016/j.molstruc.2019.126997

Cited by 8 publications

(3 citation statements)

References 49 publications

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“…Using the B3LYP function of DFT and the LanL2DZ basis set, the molecular configurations of ligands and metal complexes were adjusted to the ground-state energies . After optimization, the geometries did not exhibit hypothetical vibrational frequencies, confirming that they were low-energy structures.…”

Section: Methodsmentioning

confidence: 99%

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Noreen

Sumrra

2021

ACS Omega

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During the current study, the new aminothiazole Schiff base ligands (S 1 ) and (S 2 ) were designed by reacting 1,3thiazol-2-amine and 6-ethoxy-1,3-benzothiazole-2-amine separately with 3-methoxy-2-hydroxybenzaldehyde in good yields (68−73%). The ligands were characterized through various analytical, physical, and spectroscopic (FT-IR, UV−Vis, 1 H and 13 C NMR, and MS) methods. The ligands were exploited in lieu of chelation with bivalent metal (cobalt, nickel, copper, and zinc) chlorides in a 1:2 (M:L) ratio. The spectral (UV−Vis, FT-IR, and MS), as well as magnetic, results suggested their octahedral geometry. The theoretically optimized geometrical structures were examined using the M06/6-311G+(d,p) function of density function theory. Their bioactive nature was designated by global reactivity parameters containing a high hardness (η) value of 1.34 eV and a lower softness (σ) value of 0.37 eV. Different microbial species were verified for their potency (in vitro), revealing a strong action. The Gram-positive Micrococcus luteus and Gram-negative Escherichia coli gave the highest activities of 20 and 21 mm for compounds (8) and ( 7), respectively. The antifungal activity against the Aspergillus niger and Aspergillus terreus species gave the highest activities of 20 and 18 mm for compounds ( 7) and ( 6), respectively. The antioxidant activity, evaluated as DPPH and ferric reducing power, gave the highest inhibition (%) as 72.0 ± 0.11% (IC 50 = 144 ± 0.11 μL) and 66.3% (IC 50 = 132 ± 0.11 μL) for compounds (3) and (8), respectively. All metal complexes were found to be more biocompatible than free ligands due to their chelation phenomenon. The energies of LUMOs had a link with their activities. ■ HIGHLIGHTS• A facile synthesis of aminothiazole-containing Schiff bases and their metal chelates. • Combined experimental and theoretical exploration to decide their medicinal role. • Geometry optimization studies at the M06/6-311G +(d,p) level of density function theory. • The relative order of medicinal studies was as follows:reference drugs > metal chelates > ligands.

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Section: Methodsmentioning

confidence: 99%

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Noreen

Sumrra

2021

ACS Omega

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“…However, it is significant that, compared with the system mentioned above [97], no catalytic activity was observed in the coupling of 4-chloroacetophenone with t-butyl acrylate in DMF/K2CO3 even after 24 h at elevated temperatures. Very recently, a comparative study has been made of similar thiosemicarbazone complexes of nickel, palladium, and platinum [99]. Using a tetradentate bis-thiosemicarbazone ligand, Lima et al synthesized the complexes 7.…”

Section: In Reviews Of the Role Of Organochalcogen Ligands In Mizorokmentioning

confidence: 99%

“…Published reports of the use of thiosemicarbazone complexes as described above for the Mizoroki-Heck reaction are summarised in Table 1 for indicative reactions. Very recently, a comparative study has been made of similar thiosemicarbazone complexes of nickel, palladium, and platinum [99]. Using a tetradentate bis-thiosemicarbazone ligand, Lima et al synthesized the complexes 7.…”

Section: In Reviews Of the Role Of Organochalcogen Ligands In Mizorokmentioning

confidence: 99%

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Kostas

Steele

2020

Catalysts

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Catalysis of cross-coupling reactions under phosphane-free conditions represents an important ongoing challenge. Although transition metal complexes based on the thiosemicarbazone unit have been known for a very long time, their use in homogeneous catalysis has been studied only relatively recently. In particular, reports of cross-coupling catalytic reactions with such complexes have appeared only in the last 15 years. This review provides a survey of the research in this area and a discussion of the prospects for future developments.

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Novel κ2-Nim,S- and κ4-C,Nim,(μ-S),(μ-S)-coordination of di-2-thienyl ketone thiosemicarbazone (dtktsc). Hydrogen evolution and catalytic properties of palladacyclic [Pd(κ4-C,Nim,(μ-S),(μ-S)-dtktsc-2H)]4

Lawrence

Yamin

2020

Inorganica Chimica Acta

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Group 10 metal complexes with a tetradentate thiosemicarbazonate ligand: Synthesis, crystal structures and computational insights into the catalysis for C–C coupling via Mizoroki-Heck reaction

Cited by 8 publications

References 49 publications

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Thiosemicarbazone Complexes of Transition Metals as Catalysts for Cross-Coupling Reactions

Novel κ2-Nim,S- and κ4-C,Nim,(μ-S),(μ-S)-coordination of di-2-thienyl ketone thiosemicarbazone (dtktsc). Hydrogen evolution and catalytic properties of palladacyclic [Pd(κ4-C,Nim,(μ-S),(μ-S)-dtktsc-2H)]4

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