Reaction of diacetylmonoxime with morpholine N-thiohydrazide in the absence and in presence of a metal ion: Facile synthesis of a thiadiazole derivative with non-bonded S⋯S interaction

Biswas, Susobhan; Yap, Glenn P. A.; Dey, Kamalendu

doi:10.1016/j.poly.2009.06.091

Cited by 12 publications

(10 citation statements)

References 45 publications

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“…The hydrogen atom attached with N atom of hydrazide group can undergo thione-thiol tautomerism ( Figure 5). Thus NNS coordination mode is facilitated during the formation of complexes [34].…”

Section: Scheme Of Formation Of Ligand H 2 L 3 and Zwitterionic Hetermentioning

confidence: 95%

“…Considering the low yield of the ligand, all the complexation reactions with this ligand were carried out under in situ condition. However, the molecular thiol form of the ligand H 2 L 3 (Figure 4) was established from the structural analysis (single-crystal X-ray diffraction) of its metal complexes [34][35][36].…”

Section: Thio-hydrazone Schiff Base (H 2 L 3 ) Ligandmentioning

confidence: 99%

“…The distance between the nonbonded SÁÁÁS À is 2.738 Å, and weak interactions ( Figure 6) were observed between them in the solid state. A two dimensional supramolecular network is formed by the H-bonding and π-π interactions [34].…”

Section: Crystal Structure Of Lmentioning

confidence: 99%

“…Most interestingly, this ligand is found to show two types of binding modes (Figure 9), one is observed through N,S donor atoms and another one through N,N,S donor atoms. An efficient control over the ligand for binding through either N,S or N,N,S mode has been achieved though specific choice of metal systems [34][35][36][37][38]. (Figure 10).…”

Section: Metal Complexes With Thio-hydrazone Schiff Base (H 2 L 3 ) Lmentioning

confidence: 99%

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Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Mandal¹,

Das²,

Dey³

et al. 2020

Stability and Applications of Coordination Compounds

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The fabulous advancement of a large section of modern coordination chemistry depends upon different kinds of strategically designed and functionally tuned ligand systems; Schiff base ligands play a pivotal role among them. Such Schiff bases become more motivating when they are designed to be synthesized using very simple organic molecules. This paper reviews our work on a family of three functionally different types of Schiff base ligands, derived from diacetylmonoxime, which have been employed to synthesize mononuclear metal complexes with various binding modes of ligands and topologies around the metal centers. Such Schiff base ligands have been synthesized by reacting diacetylmonoxime with diethylenetriamine, 1,3-diaminopropane-2-ol, and morpholine N-thiohydrazide. The synthesized Schiff bases and the metal complexes of such "privileged ligands" show many interesting supramolecular coordination architectures involving different weak forces, e.g., H-bonding, C-HÁÁÁπ interactions, etc.

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Section: Scheme Of Formation Of Ligand H 2 L 3 and Zwitterionic Hetermentioning

confidence: 95%

Section: Thio-hydrazone Schiff Base (H 2 L 3 ) Ligandmentioning

confidence: 99%

Section: Crystal Structure Of Lmentioning

confidence: 99%

Section: Metal Complexes With Thio-hydrazone Schiff Base (H 2 L 3 ) Lmentioning

confidence: 99%

See 2 more Smart Citations

Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Mandal¹,

Das²,

Dey³

et al. 2020

Stability and Applications of Coordination Compounds

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“…Generally, carbothioamides belong to thiourea group, which was recognized to possess a wide range of industrial applications as catalysts [6,7], inhibitors [8] and for extraction of the toxic metals [9] as well as diverse biological activity [3,[10][11][12]. The coordinating ability of N,S-ligands permitted them to form complexes of intriguing research applications [13][14][15]. For example, Ni(II) complexes of thiourea derivatives were attracted much attention because of their use as models for the nickel center of enzymes [16].…”

Section: Introductionmentioning

confidence: 99%

Thermal, spectral, DFT and biological activity evaluation of Co(II), Ni(II) and Cu(II) complexes of N,S-chelated benzotriazole ligand

Mansour

2015

J Therm Anal Calorim

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ML 2 ]ÁyC 2 H 5 OHÁzH 2 O complexes (M=Co II (1) and Ni II (2), y = 4, z = 0; M=Cu II (3), y = 0, z = 3; HL = N-(2-thiazolyl)-1H-benzotriazole-1-carbothioamide) were prepared, characterized (elemental analysis, TG, FT IR, UV-Vis, EPR, magnetic and conductance measurement) and tested for their antimicrobial activity against Escherichia coli and Staphylococcus aureus. Complexes 1-3 consist of a metal center having a considerable tetrahedral distortion in the xy-plane from the square planar stereochemistry MN 2 S 2 formed by the two deprotonated benzotriazole ligands. TD-DFT calculations were carried out at B3LYP/6-31G * level of theory to understand the electronic structure and to explain the related experimental findings. Natural bond orbital analysis was performed to provide details about the electronic arrangement, type of hybridization and the nature of bonding. Coordination of HL to Co II gave rise to inactive compound, but the development of Ni II and Cu II complexes did not clearly change the toxicity of the free HL.

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Correlating Structure and KA² Catalytic Activity of Zn^II Hydrazone Complexes

Adejumo,

Danopoulou,

Zorba

et al. 2023

Eur J Inorg Chem

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Two new Zn(II) complexes bearing tridentate hydrazone‐based ligands with NNO or NNS donor atoms were synthesised and characterised by elemental analysis, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies, and single crystal X‐ray diffraction methods. These complexes, together with four previously synthesised analogues, having hydrazone ligands with a NNO donor set of atoms, were successfully employed as catalysts in the ketone‐amine‐alkyne (KA2) coupling reaction, furnishing tetrasubstituted propargylamines, compounds with unique applications in organic chemistry. DFT calculations at the CAM‐B3LYP/TZP level of theory were performed to elucidate the electronic structure of the investigated Zn(II) complexes, excellently correlating the structure of the complexes to their catalytic reactivity.

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Reaction of diacetylmonoxime with morpholine N-thiohydrazide in the absence and in presence of a metal ion: Facile synthesis of a thiadiazole derivative with non-bonded S⋯S interaction

Cited by 12 publications

References 45 publications

Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Thermal, spectral, DFT and biological activity evaluation of Co(II), Ni(II) and Cu(II) complexes of N,S-chelated benzotriazole ligand

Correlating Structure and KA² Catalytic Activity of Zn^II Hydrazone Complexes

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Reaction of diacetylmonoxime with morpholine N-thiohydrazide in the absence and in presence of a metal ion: Facile synthesis of a thiadiazole derivative with non-bonded S⋯S interaction

Cited by 12 publications

References 45 publications

Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Crystal Structure and Solid-State Properties of Metal Complexes of the Schiff Base Ligands Derived from Diacetylmonoxime: A Brief Review

Thermal, spectral, DFT and biological activity evaluation of Co(II), Ni(II) and Cu(II) complexes of N,S-chelated benzotriazole ligand

Correlating Structure and KA2 Catalytic Activity of ZnII Hydrazone Complexes

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Correlating Structure and KA² Catalytic Activity of Zn^II Hydrazone Complexes