Synthesis, structural elucidation, and catalytic activity of bimetallic rhenium-tin complexes containing Schiff base ligand

Kaur, Manpreet; Kapila, Akanksha; Yempally, Veeranna; Kaur, Harminder

doi:10.1016/j.molstruc.2021.131545

Cited by 8 publications

(15 citation statements)

References 56 publications

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“…The compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were analyzed against two fungal (Candida albicans (MTCC 227), Aspergillus niger (MTCC 7678), two gram-negative (Escherichia coli (MTCC 732) and Pseudomonas aeruginosa (MTCC 424) and two grampositive (Staphylococcus aureus (MTCC 2901), Bacillus subtilis (NCIM 2063) strains via serial dilution assay 33 in triplicates using standard drugs (fluconazole and ciprofloxacin) to assess their in vitro antimicrobial efficacy.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…[12][13][14][15] These compounds possess a diverse range of biological activities, making them attractive candidates for drug development. 16 Diorganotin (IV) complexes are a class of chemical compounds that consist of a central tin atom that is covalently bonded to two organic groups and various ligands, which makes them versatile and useful in different areas such as catalysis, 17 polymer chemistry, 18 biological activity [19][20][21] and material science. Among various ligand scaffolds used in tin complexes, hydrazones are notable for their unique chelating properties owing to the presence of an additional chelating center as C=O in addition to the functional group (HN=CH)C=, which allows them to coordinate with different metal ions as either protonated or deprotonated species, forming a diverse array of homo-and hetero-chelates with distinct geometrical structures.…”

Section: Introductionmentioning

confidence: 99%

“…In the search of novel and effective anti-infectious agents, new hydrazone ligands (1)(2)(3)(4) and their diorganotin (IV) complexes (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were synthesized by condensing piperonylic hydrazide with salicylaldehyde derivatives, which have been further characterized by numerous physical and spectral techniques [ 1 H, 13 C, 119 Sn] NMR, mass spectroscopy, UV-Vis, IR). These techniques ascertained dibasic tridentate coupling of hydrazone ligands with diorganotin (IV) through phenolic, enolic oxygens, and imine nitrogen, demonstrating pentacoordinated stereochemistry of the complexes.…”

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confidence: 99%

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Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Taxak,

Devi,

Dubey

et al. 2023

Applied Organom Chemis

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In the search of novel and effective anti‐infectious agents, new hydrazone ligands (1–4) and their diorganotin (IV) complexes (5–20) were synthesized by condensing piperonylic hydrazide with salicylaldehyde derivatives, which have been further characterized by numerous physical and spectral techniques [1H, 13C, 119Sn] NMR, mass spectroscopy, UV–Vis, IR). These techniques ascertained dibasic tridentate coupling of hydrazone ligands with diorganotin (IV) through phenolic, enolic oxygens, and imine nitrogen, demonstrating pentacoordinated stereochemistry of the complexes. The thermal stability of up to 160°C of the complexes was ascertained by TGA studies whereas low conductance signified compounds have non‐electrolytic nature. Further, the antimicrobial activity was evaluated against four bacterial and two fungal strains by serial dilution assay, which demonstrated that the metal complexes (10, 11, 12) have comparable MIC values (0.0085–0.0098 μmol/ml) with ciprofloxacin and excellent biological responses in comparison of fluconazole. The phenyl complex [Ph2SnL2] (12) was found to be the most active antimicrobial agent with the lowest MIC value (0.0085 μmol/ml). The compounds were also screened for in vitro anti‐inflammatory activity by BSA denaturation assay and the phenyl complex [Ph2SnL2] (12) has been reported as most potent with 7.62 IC50 value, which is comparable with diclofenac sodium. Further, the biologically active complexes (9–12) and their hydrazone ligand [H2L2] were theoretically analyzed by computational investigations to support the in vitro results. The molecular docking analysis of compounds was performed on the active site of C. albicans (PDB ID: 5V5Z) and E. coli (PDB ID: 1HNJ) to assess the binding interactions and binding energy. The DFT and MESP (2, 9–12) revealed the most reactive areas, molecular geometry, Mulliken atomic charges, electronegativity, etc. of the compounds (2, 9–12). The ADMET profile showed the toxicity level and drug‐likeness properties, showing their potential to operate as viable antagonists.

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Section: Antimicrobial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Taxak,

Devi,

Dubey

et al. 2023

Applied Organom Chemis

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“…Organotin(IV) derivatives have been given special consideration because of the stable bonds formed by tin with carbon atoms, as well as with heteroatoms [ 10 , 11 , 12 ]. Particular consideration has been given to organotin complexes derived from Schiff bases, since these bases provide a wide variety of molecular structural conformations as ligands [ 13 , 14 , 15 , 16 , 17 ]. Moreover, complexes with Schiff bases show thermo- and photostability, are easy to synthesize and have the versatility to tune optical and optoelectronic properties through the chemical modulation of the ligands [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Pentacoordinated Organotin(IV) Complexes as an Alternative in the Design of Highly Efficient Optoelectronic and Photovoltaic Devices: Synthesis and Photophysical Characterization

Sánchez-Vergara

Gómez

Dircio

et al. 2023

IJMS

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The synthesis of four pentacoordinated organotin(IV) complexes prepared in a one-pot reaction from 2-hydroxy-1-naphthaldehyde, 2-amino-3-hydroxypyridine and organotin oxides is reported. The complexes were characterized by UV-Vis, IR, MS, 1H, 13C and 119Sn NMR techniques. The compound based on 2,2-diphenyl-6-aza-1,3-dioxa-2-stannanaphtho[1,2-h]pyrido[3,2-d]cyclononene revealed the formation of a monomeric complex with a distorted five-coordinated molecular geometry intermediate between the trigonal bipyramidal and square pyramidal. In order to find possible applications in photovoltaic devices, hybrid films of organotin(IV) complexes embedded in poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) with graphene were deposited. The topographic and mechanical properties were examined. The film with the complex integrated into the cyclohexyl substituent has high plastic deformation, with a maximum stress of 1.69 × 107 Pa and a Knoop hardness of 0.061. The lowest values of 1.85 eV for the onset gap and 3.53 eV for the energy gap were obtained for the heterostructure having the complex with the phenyl substituent. Bulk heterojunction devices were fabricated; these devices showed ohmic behavior at low voltages and a space-charge-limited current (SCLC) conduction mechanism at higher voltages. A value of 0.02 A was found for the maximum carried current. The SCLC mechanism suggests hole mobility values of between 2.62 × 10−2 and 3.63 cm2/V.s and concentrations of thermally excited holes between 2.96 × 1018 and 4.38 × 1018 m−3.

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“…Organotin(IV) compounds as catalyst have also reached distinct statures due to, in a great extent, absence of side reactions, good efficiency even under mild conditions, and encouraging toxicological and environmental properties 3 . Organotin(IV) compounds have therefore been employed as industrial catalysts for esterification, polyvinyl chloride (PVC) stabilization, and polyurethane formation, 4 and their use as catalyst continues to appear in the literature 5–11 …”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

Basu Baul,

Khatiwara,

Addepalli

et al. 2023

Applied Organom Chemis

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Diorganotin(IV) complexes of composition [Me2SnL] (1), [n‐Bu2SnL] (2), and [Bz2SnL] (3) were synthesized by reacting the N2,N6‐di(pyridin‐2‐yl)pyridine‐2,6‐dicarboxamide pro‐ligand (H2L, where H2 denotes the two acidic protons) with Me2SnO, n‐Bu2SnO, and Bz2SnO, respectively, in refluxing toluene. The amide ligand leads to highly stable diorganotin(IV) complexes via the dianionic tridentate donor set (Npy, N−, N−) with pendent pyridine arms, and the coordination domain is completed by the respective two alkyl ligands. Solution‐state structures of the compounds 1–3 were studied by 1H, 13C, and 119Sn nuclear magnetic resonance (NMR) spectroscopy, revealing that the complexes adopt a five‐coordinate structure in non‐coordinating solvent. Additionally, homogenity and purity of the bulk materials of 1–3 were judged using the high‐resolution mass spectrometry in acetonitrile solution. The molecular and crystal structures of 1·0.5C6H6, 2, and 3 in the solid phase were established by single‐crystal X‐ray diffraction analysis. For all three compounds, the core defined by the rigid tridentate pyridine dicarboxamide ligand and the Sn‐coordinating C atoms adopts nearly C2v symmetry and thus matches none of the most popular geometries for five‐coordinated species, namely square‐pyramidal or trigonal‐bipyramidal coordination. Thermogravimetric analysis (TGA) was performed to probe the thermal stabilities of 1–3. The results serve as a basis for designing highly efficient diorganotin(IV) mimics for catalytic applications. Catalytic studies of ε‐caprolactone formation via Baeyer–Villiger oxidation of cyclohexanone with aqueous H2O2 were performed under microwave (MW) irradiation. The consequences of several reaction parameters like catalyst quantity, time, temperature, and solvent were studied.

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Synthesis, structural elucidation, and catalytic activity of bimetallic rhenium-tin complexes containing Schiff base ligand

Cited by 8 publications

References 56 publications

Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Pentacoordinated Organotin(IV) Complexes as an Alternative in the Design of Highly Efficient Optoelectronic and Photovoltaic Devices: Synthesis and Photophysical Characterization

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

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