Search results for: divalent metal complexes of schiff bases

Authors: Srinivas Nerella

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A series of new heterodentate N, O-donor ligands derived from condensing 3-amino Coumarins with hydroxy benzaldehydes and acetophenones were used to afford new mononuclear Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Pd(II) coordination compounds. All the complexes were characterized by IR, 1H-NMR, 13C-NMR, Mass, ESR, Electronic spectra, Conductance, Magnetic and Thermal studies. The ligands show hexa coordination in Mn(II), Co(II), Ni(II), and Pd(II) complexes resulting octahedral geometries, while the ligands in Zn(II) and Cu(II) complexes show tetra coordination resulting tetrahedral and square planar geometries respectively. These mononuclear complexes were investigated as catalysts in the hydrothiolation of aromatic and aliphatic alkynes with thiols. These metal complexes were acted as versatile catalysts and gave good yields.

Keywords: schiff bases, divalent metal complexes of schiff bases, Catalytic activity, hydrothiolation

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Authors: Ahmed A. Farag, M. A. Hgazy

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The influence of three Schiff bases (SB-I, SB-II, and SB-III) on the corrosion of carbon steel in 0.5 M H2SO4 solution was studied by potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) techniques. The inhibition efficiency increases with the concentration of the Schiff bases and follow the trend: SB-III > SB-II > SB-I. Tafel polarization measurements revealed that the three tested inhibitors function as anodic inhibitors. The thermodynamic parameters Kads and ΔGºads are calculated and discussed. The Langmuir isotherm equation was found to provide an accurate description of the adsorption behaviour of the investigated Schiff bases. Depending on the results, the inhibitive mechanism was proposed.

Keywords: Schiff bases, corrosion inhibitors, EIS, adsorption

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Authors: M. Belhadj Lachachi, Tayeb Benabdallah, M. Hadj Youcef, Jason M. Lynama

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The application of inorganic chemistry to catalysis and environmental chemistry is a rapidly developing field, and novel catalytic metal complexes are now having an impact on the industrial development practice. Advances in organometallic chemistry are crucial for improving the design of compounds to reduce toxic side effects and understand their mechanisms of action. The reaction of platinum(II) organometallic complexes with bidentate Schiff bases derived from 2-Hydroxynaphtalydeneaniline have been carried out. It concerns N,N’-naphtalidene para-nitroaniline (1-a), the, the N,N’-naphtalidene para-ethoxyaniline (1-b), the N,N’-naphtalideneaniline (1-c), the N,N’-naphtalidene para-chloroaniline (1-d) and the N,N’-naphtalidene para-methoxyaniline (1-e). The ligands were fully characterized by I.R., elemental analysis, 1H-NMR, 13C-NMR, ESI Mass Spectrometry and X-Ray Diffraction. The resulting metal complexes were obtained as a cationic species, through a simple substitution reaction, leading to two geometric isomers [1, 2], and characterized by IR, 1H-NMR, 13C-NMR, LIFDI Mass Spectrometry and supported by Elemental Analysis and X-Ray diffraction. Furthermore, a bimetallic platinum complex was prepared from the same ligands and dichloro(1,5-cyclooctadiene)platinum and characterized by X-Ray diffraction [3]The catalytic properties of the prepared platinum complexes in the hydrogenative and dehydrogenative silylation of styrene were investigated, and reaction kinetics conversion to products was determined by 1H-NMR and confirmed by GC-MS. This presentation will detail a comparison of the catalytic activity of five platinum organometallic complexes bearing different Schiff base ligands in the hydrosilylation of styrene, varying the experimental conditions of temperature, nature of the complex and the loading of the catalyst.

Keywords: catalysis, hydrosilylation, organometallic, schiff base

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Authors: Lekha Logu

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The coordination behavior of the newly synthesized Schiff base ligands, 4-bromo-2-((p-tolyl imino) methyl) phenol obtained by condensing para-toluidine with 5-bromo salicylaldehyde and N-(3,4-dichloro benzylidene)-4-methylbenzenamine obtained by condensing Para-toluidine with 3,4-dichloro benzaldehyde in ethanolic medium has been explored in this current study. The synthesized Schiff’s base ligands were complexed with lanthanide nitrate salts yielding [LnL(NO3)2(H2O)2]NO3, (Ln=Pr, Sm). Elemental analysis, conductance measurement, and spectral techniques like Nuclear Magnetic Resonance (NMR), Ultraviolet-visible (UV-Vis) and Fourier Transform Infrared (FTIR) have been used to characterize Schiff’s base ligands and their lanthanide metal complexes. An attempt has been made on these complexes for their antimicrobial activity against the gram-positive and gram-negative bacterial species like Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumonia and fungal species like Canadida and Aspergillus.

Keywords: lanthanide complexes, Schiff's base, antimicrobial assay, synthesis, characterization

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Authors: Lynda Golea, Rachid Chebaki

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Schiff bases contain heterocyclic structural units with N and O donor atoms which plays an important role in coordination chemistry. Azomethine groups are a broad class of widely used compounds with applications in many fields, including analytical, inorganic chemistry and biological. Schiff's base is of promising research interest due to the widespread antibacterial resistance in medical science. In addition, the research is essential to generate Schiff base metal complexes with various applications. Schiff complexes have been used as drugs and have antibacterial, antifungal, antiviral, and anti-inflammatory properties. The various donor atoms they contain offer a special ability for metal binding. In this research on the physicochemical properties of azomethine groups, we synthesized and studied the Schiff base compounds by a condensation reaction of tryptamines and acetophenone in ethanol. The structure of the prepared compound was interpreted using 1H NMR, 13C NMR, UV-vis and FT-IR. A computational analysis at the level of DFT with functional B3LYP in conjunction with the base 6-311+G (d, p) was conducted to study its electronic and molecular structure. The biological study was performed on three bacterial strains usually causing infection, including Gram-positive and Gram-negative, for antibacterial activity. Results showed moderate biological activity and proportional activity with increasing concentration.

Keywords: azomethine, HOMO, LUMO, RMN, molecular docking

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Authors: D. J. Madhu Kumar, D. Jagadeesh Prasad, Sana Sheik, E. P. Rejeesh

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A series of Mannich bases derived from 1,2,4-triazole(3a-k and 4a-k) are synthesized by treating a Schiff base with various substituted primary/secondary amines and formaldehyde. The Schiff base is prepared by treating 3-methyl-4-amino-5-mercapto-1,2,4-triazole with 3,4-dimethoxybenzaldehyde in the presence of acid catalyst. The triazole is prepared by treating acetic acid with thiocarbohydrazide at reflux temperature. All the synthesized samples are characterised by FT-IR, 1H-NMR, and LC-MASS spectral studies and screened for their anti-oxidant activity.

Keywords: mannich bases, anti-oxidant activity, schiff base, triazole

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Authors: Mohamedou El Boukhary, Farba Bouyagui Tamboura, A. Hamady Barry, T. Moussa Seck, Mohamed L. Gaye

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Nowadays, low-schiff acyl-hydrazone ligands are highly sought after due to their wide applications in various fields of biology, coordination chemistry, and catalysis. They are studied for their antioxidant, antibacterial and antiviral properties. The complexes of transition metals and the lanthanide they derive are well known for their magnetic, optical, and catalytic properties. In this work, we present the synthesis of an acyl-hydrazone (H2L) schiff base and their 3d transition complexes. The ligand (H2L) is characterized by IR, NMR (1H; 13C) spectroscopy. The complexes are characterized by different physic-chemical techniques such as IR, UV-visible, conductivity, measurement of magnetic susceptibility. The study of XRD allowed us to elucidate the crystalline structure of the manganese (Mn) complex. The asymmetric unit of the complex is composed of two molecules of the ligand, one manganese (II) ion, and two coordinate chloride ions; the environment around Mn is described as a pentagonal base bipyramid. In the crystal lattice, the asymmetric unit is bound by hydrogen bonds.

Keywords: synthene, acyl-hydrazone, 3D transition metal complex, application

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Authors: Imran Muhammad

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The main cause of infectious disease in the modern world is Mycobacterium Tuberculosis (MT). To combat tuberculosis, new and efficient drugs are an urgent need in the modern world. Schif bases are potent for their biological pharmacophore activity. Thus we selected different Vanillin-based Schiff bases for their binding activity against target enzymes of Mycobacterium tuberculosis that is (DprE1 (decaprenyl phosphoryl-β-D-ribose 2′-epimerase), and DNA gyrase subunit-A), using molecular docking. We evaluate the inhibition potential, interaction, and binding mode of these compounds with the target enzymes.

Keywords: schiff bases, tuberculosis, DNA gyrase, DprE1, docking

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Authors: Neslihan Beyazit, Sahin Bayraktar, Cahit Demetgul

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Transition metal ions have an important role in biochemistry and biomimetic systems and may provide the basis of models for active sites of biological targets. The presence of copper(II), iron(II) and zinc(II) is crucial in many biological processes. Tetradentate N2O2 donor Schiff base ligands are well known to form stable transition metal complexes and these complexes have also applications in clinical and analytical fields. In this study, we present salient structural features and the details of cathecholase activity of Fe(II) complex of a new Schiff Base ligand. A new asymmetrical N2O2 donor Schiff base ligand and its Fe(II) complex were synthesized by condensation of 4-nitro-1,2 phenylenediamine with 6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one and by using an appropriate Fe(II) salt, respectively. Schiff base ligand and its metal complex were characterized by using FT-IR, 1H NMR, 13C NMR, UV-Vis, elemental analysis and magnetic susceptibility. In order to determine the kinetics parameters of catechol oxidase-like activity of Schiff base Fe(II) complex, the oxidation of the 3,5-di-tert-butylcatechol (3,5-DTBC) was measured at 25°C by monitoring the increase of the absorption band at 390-400 nm of the product 3,5-di-tert-butylcatequinone (3,5-DTBQ). The compatibility of catalytic reaction with Michaelis-Menten kinetics also investigated by the method of initial rates by monitoring the growth of the 390–400 nm band of 3,5-DTBQ as a function of time. Kinetic studies showed that Fe(II) complex of the new N2O2 donor Schiff base ligand was capable of acting as a model compound for simulating the catecholase properties of type-3 copper proteins.

Keywords: catecholase activity, Michaelis-Menten kinetics, Schiff base, transition metals

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Authors: Laila H. Abdel-Rahman, Mohamed Shaker S. Adam, Ahmed M. Abu-Dief, Hanan El-Sayed Ahmed

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In this investigation, Cu(II), Pd(II) and Ag(I) complexes with the tetra-dentate DSPH Schiff base ligand were synthesized. The DSPH Schiff base and its complexes were characterized by using different physicochemical and spectral analysis. The results revealed that the metal ions coordinated with DSPH ligand through azomethine nitrogen and phenolic oxygen. Cu(II), Pd(II) and Ag(I) complexes are present in a 1:1 molar ratio. Pd(II) and Ag(I) complexes have square planar geometries while, Cu(II) has a distorted octahedral (Oh) geometry. All investigated complexes are nonelectrolytes. The investigated compounds were tested against different strains of bacteria and fungi. Both prepared compounds showed good results of inhibition against the selected pathogenic microorganism. Moreover, the interaction of investigated complexes with CT-DNA was studied via various techniques and the binding modes are mainly intercalative and grooving modes. Operating Environment MOE package was used to do docking studies for the investigated complexes to explore the potential binding mode and energy. Furthermore, the growth inhibitory effect of the investigated compounds was examined on some cancer cells lines.

Keywords: tetradentate, antimicrobial, CT-DNA interaction, docking, anticancer

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Authors: Roghaye Behroozi

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The development of functionalized metal complexes and nanomaterials has gained significant attention due to their potential in catalyzing selective oxidation and coupling reactions. These catalysts play a crucial role in various industrial and pharmaceutical processes, enhancing the efficiency, selectivity, and sustainability of chemical reactions. This research aims to design and synthesize new functionalized metal complexes and nanomaterials to explore their catalytic applications in the selective oxidation of alcohols and coupling reactions, focusing on improving yield, selectivity, and catalyst reusability. The study involves the synthesis of a nickel Schiff base complex stabilized within 41-MCM as a heterogeneous catalyst. A Schiff base ligand derived from glycine was used to create a tin (IV) metal complex characterized through spectroscopic techniques and computational analysis. Additionally, iron-based magnetic nanoparticles functionalized with melamine were synthesized for catalytic evaluation. Lastly, a palladium (IV) complex was prepared, and its oxidative stability was analyzed. The nickel Schiff base catalyst showed high selectivity in converting primary and secondary alcohols to aldehydes and ketones, with yields ranging from 73% to 90%. The tin (IV) complex demonstrated accurate structural and electronic properties, with consistent results between experimental and computational data. The melamine-functionalized iron nanoparticles exhibited efficient catalytic activity in producing triazoles, with enhanced reaction speed and reusability. The palladium (IV) complex displayed remarkable stability and low reactivity towards C–C bond formation due to its symmetrical structure. The synthesized metal complexes and nanomaterials demonstrated significant potential as efficient, selective, and reusable catalysts for oxidation and coupling reactions. These findings pave the way for developing environmentally friendly and cost-effective catalytic systems for industrial applications.

Keywords: catalysts, Schiff base complexes, metal-organic frameworks, oxidation reactions, nanoparticles, reusability

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Authors: Ertuğ Yıldırım, Dile Kara, Salih Zeki Yıldız

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Metal containing polymers (MCPs) are macro molecules usually containing metal-ligand coordination units and are a multidisciplinary research field mainly based at the interface between coordination chemistry and polymer science. The progress of this area has also been reinforced by the growth of several other closely related disciplines including macro molecular engineering, crystal engineering, organic synthesis, supra molecular chemistry and colloidal and material science. Schiff base ligands are very effective in constructing supra molecular architectures such as coordination polymers, double helical and triple helical complexes. In addition, Schiff base derivatives incorporating a fluorescent moiety are appealing tools for optical sensing of metal ions. MCPs are well-known systems in which the combinations of local parameters are possible by means of fluoro metric techniques. Generally, without incorporation of the fluorescent groups with polymers is unspecific, and it is not useful to analyze their fluorescent properties. Therefore, it is necessary to prepare a new type epoxy polymers with fluorescent groups in terms of metal sensing prop and the other photo chemical applications. In the present study metal containing polymers were prepared via poly functional monomeric Schiff base metal chelate complexes in the presence of dis functional monomers such as diglycidyl ether Bisphenol A (DGEBA). The synthesized complexes and polymers were characterized by FTIR, UV-VIS and mass spectroscopies. The preparations of epoxy polymers have been carried out at 185 °C. The prepared composites having sharp and narrow excitation/emission properties are expected to be applicable in various systems such as heat-resistant polymers and photo voltaic devices. The prepared composite is also ideal for various applications, easily prepared, safe, and maintain good fluorescence properties.

Keywords: Schiff base ligands, crystal engineering, fluorescence properties, Metal Containing Polymers (MCPs)

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Authors: Baki Cicek, Umit Calisir

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Carbazoles have been replaced lots of studies from 1960's to present and also still continues. In 1987, the first diode device had been developed. Thanks to that study, light emitting devices have been investigated and developed and also have been used on commercial applications. Nowadays, OLED (Organic Light Emitting Diodes) technology is using on lots of electronic screen such as (mobile phone, computer monitors, televisions, etc.) Carbazoles were subject a lot of study as a semiconductor material. Although this technology is used commen and widely, it is still development stage. Metal complexes of these compounds are using at pigment dyes because of colored substances, polymer technology, medicine industry, agriculture area, preparing rocket fuel-oil, determine some of biological events, etc. Becides all of these to preparing of schiff base synthesis is going on intensely. In this study, some of novel carbazole schiff bases were synthesized starting from carbazole. For that purpose, firstly, carbazole was alkylated. After purification of N-substituted-carbazole was nitrated to sythesized 3-nitro-N-substituted and 3,6-dinitro-N-substituted carbazoles. At next step, nitro group/groups were reduced to amines. Purified with using a type of silica gel-column chromatography. At the last step of our study, with sythesized 3,6-diamino-N-substituted carbazoles and 3-amino-N-substituted carbazoles were reacted with aldehydes to condensation reactions. 3-(imino-p-hydroxybenzyl)-N-isobutyl -carbazole, 3-(imino-2,3,4-trimethoxybenzene)-N-butylcarbazole, 3-(imino-3,4-dihydroxybenzene)-N-octylcarbazole, 3-(imino-2,3-dihydroxybenzene)-N-octylkarbazole and 3,6-di(α-imino-β-naphthol) -N-hexylcarbazole compounds were synthesized. All of synthesized compounds were characterized with FT-IR, 1H-NMR, 13C-NMR, and LC-MS.

Keywords: carbazole, carbazol schiff base, condensation reactions, OLED

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Authors: N. Belhadj, M. Hadj Youcef, T. Benabdallah, Belbachir Ibtissem, N. Boceiri

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This work deals with the synthesis, the structural elucidation and the exploration the extracting properties of a series of ortho-hydroxy Schiff base in sulfate medium. After the synthesis and characterization of their structures, the study of their behavior in solution was carried out by pH-metric titration in different media homogeneous and heterogeneous solution. This allowed to explore and to quantify in each of these media, some of their properties in solution such as, their acid-base behavior (determination and comparison of pKa), their distribution powers (determination and comparison of logKd), and their thermodynamic constants (determining ∆H°, ΔS° and ∆G°moy) by optimizing both the temperature and ionic strength. Study of the extraction of nickel (II) and cobalt(II) separately was undertaken in the aqueous-organic system, chloroform-water. Different extraction parameters have been thus optimized such, the pH, the concentration of extractant and the ionic strength, and the extraction constants established in each case. The extracted metal complexes have been isolated and their spatial configurations elucidated. The selective extraction of the couple cobalt (II)/nickel (II) was finally performed by our series of Schiff base in the chloroforme/water.

Keywords: selective extraction, Schiff base, distribution, cobalt(II), nickel(II)

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Authors: Maryam Nejat Dehkordi, Per Lincoln, Hassan Momtaz

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Interaction of Schiff base complexes of iron and manganese (iron [N, N’ Bis (5-(triphenyl phosphonium methyl) salicylidene) -1, 2 ethanediamine) chloride, [Fe Salen]Cl, manganese [N, N’ Bis (5-(triphenyl phosphonium methyl) salicylidene) -1, 2 ethanediamine) acetate) with DNA were investigated by spectroscopic and isothermal titration calorimetry techniques (ITC). The absorbance spectra of complexes have shown hyper and hypochromism in the presence of DNA that is indication of interaction of complexes with DNA. The linear dichroism (LD) measurements confirmed the bending of DNA in the presence of complexes. Furthermore, isothermal titration calorimetry experiments approved that complexes bound to DNA on the base of both electrostatic and hydrophobic interactions. Furthermore, ITC profile exhibits the existence of two binding phases for the complex. Antibacterial activity of ligand and complexes were tested in vitro to evaluate their activity against the gram positive and negative bacteria.

Keywords: Schiff base complexes, ct-DNA, linear dichroism (LD), isothermal titration calorimetry (ITC), antibacterial activity

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Authors: Abdol-Hassan Doulah

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In this research, some of the inorganic complexes of uranyl with N- donor ligands were synthesized. Complexes were characteriezed by FT-IR and UV spectra, ¹HNMR, ¹³CNMR and some physical properties. The uranyl unit (UO2) is composed of a center of uranium atom with the charge (+6) and two oxygen atom by forming two U=O double bonds. The structure is linear (O=U=O, 180) and usually stable. So other ligands often coordinate to the U atom in the plane perpendicularly to the O=U=O axis. The antitumor activity of some of ligand and their complexes against a panel of human tumor cell lines (HT29: Haman colon adenocarcinoma cell line T47D: human breast adenocarcinoma cell line) were determined by MTT(3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide) assay. These data suggest that some of these compounds provide good models for the further design of potent antitumor compounds.

Keywords: inorganic, uranyl complex-donor ligands, Schiff bases, anticancer activity

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Authors: Rihana Hadjeb, Djamel Barkat

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Schiff bases derived from o-hydroxybenzaldehyde has attracted a great interest not only for its promising applications towards linear and non-linear optical properties, biological activity and technological applications but also used as model compounds for the theory of hydrogen bonding. Due to its intramolecular hydrogen bonding, depending on the position of proton in the hydrogen bond o-hydroxy salicylidene Schiff bases exhibit two tautomeric forms, enol-imine (E-form) and keto-enamine (K-form) both in solution and in crystalline state. A zwitterionic structure also appears due to a proton transfer in enol – imine and keto – amine tautomer. These classes of compounds also exhibit thermochromic and photochromic behavior. We undertook in this study the synthesis of ten compounds of hydroxy Schiff bases from the condensation of salicylic aldehyde and aniline substituted in the ortho, meta and para by the methyl, chloro and nitro groups. To study the keto-enol equilibrium of the compounds; UV-VIS spectra were studied in different polarity solvents. The compounds were in tautomeric equilibrium (enol imine O–H•••N, keto-amine O•••H–N forms). For some derivatives of salicylideneanilines the keto-amine form was observed in both ethanol and dioxane. IR results showed that all Schiff bases studied favor the enol-imine form over the keto form.

Keywords: salicylideneaniline, tautomerism, keto-enol equilibrium, UV-VIS spectroscopy, solvent effect

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Authors: Harminder Kaur, Manpreet Kaur, Akanksha Kapila, Reenu

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Schiff base with general formula H₂L was derived from condensation of o-vanillin and 3-nitro-o-phenylenediamine. This Schiff base was used for the synthesis of organotin(IV) complexes with general formula R₂SnL [R=Phenyl or n-octyl] using equimolar quantities. Elemental analysis UV-Vis, FTIR, and multinuclear spectroscopic techniques (¹H, ¹³C, and ¹¹⁹Sn) NMR were carried out for the characterization of the synthesized complexes. These complexes were coloured and soluble in polar solvents. Computational studies have been performed to obtain the details of the geometry and electronic structures of ligand as well as complexes. Geometry of the ligands and complexes have been optimized at the level of Density Functional Theory with B3LYP/6-311G (d,p) and B3LYP/MPW1PW91 respectively followed by vibrational frequency analysis using Gaussian 09. Observed ¹¹⁹Sn NMR chemical shifts of one of the synthesized complexes showed tetrahedral geometry around Tin atom which is also confirmed by DFT. HOMO-LUMO energy distribution was calculated. FTIR, ¹HNMR and ¹³CNMR spectra were also obtained theoretically using DFT. Further IRC calculations were employed to determine the transition state for the reaction and to get the theoretical information about the reaction pathway. Moreover, molecular docking studies can be explored to ensure the anticancer activity of the newly synthesized organotin(IV) complexes.

Keywords: DFT, molecular docking, organotin(IV) complexes, o-vanillin, 3-nitro-o-phenylenediamine

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Authors: Shannen Lorraine, Paul Maragh, Tara Dasgupta, Kamaluddin Abdur-Rashid

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(R)-(4,4',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (R-Ph-Garphos), and (S)-(4,4',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (S-Ph-Garphos) are novel, nucleophilic, chiral atropisomeric ligands. The research explored the synthesis of chiral transition metal complexes containing these ligands and their applications in various asymmetric catalytic transformations. Herein, the transition metal complexes having ruthenium(II), rhodium(I) and iridium(I) metal centres will be discussed. These are air stable complexes and were characterized by CHN analysis, 1H, 13C, and 31P NMR spectroscopy, and polarimetry. Currently, there is an emphasis on 'greener' catalysts and the need for 'green' solvents in asymmetric catalysis. As such, the Ph-Garphos ligands were demethylated thereby introducing hydroxyl moieties unto the ligand scaffold. The facile tunability of the biaryl diphosphines led to the preparation of the (R)-(4,4',6,6'-tetrahydroxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (R-Ph-Garphos-OH), and (S)-(4,4',6,6'-tetrahydroxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (S-Ph-Garphos-OH) ligands. These were successfully characterized by CHN analysis, 1H, 13C, and 31P NMR spectroscopy, and polarimetry. The use of the Ph-Garphos and Ph-Garphos-OH ligands and their transition metal complexes in asymmetric hydrogenations will be reported. Additionally, the scope of the research will highlight the applicability of the Ph-Garphos-OH ligand and its transitional metal complexes as 'green' catalysts.

Keywords: catalysis, asymmetric hydrogenation, diphosphine transition metal complexes, Ph-Garphos ligands

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Authors: Dhivya Arumugam, Kaliyappan Thananjeyan

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The monomer of (3-((4-(methacryloyloxy)phenylimino)methyl)-2-hydroxybenzoic acid) schiff base polymer was prepared by reacting methacryloyl chloride with imine compound derived from 3-formylsalisylic acid and 4- aminophenol. The monomer was polymerized in DMF at 70oC using benzoyl peroxide as free radical initiator. Polymer metal complex was obtained in DMF solution of polymer with aqueous solution of metal ions. The polymer and the polymer metal complex were characterized by elemental analysis and spectral studies. The elemental analysis data suggest that the metal to ligand ratio is 1:1 and hence, it acts as a binucleating compartmental ligand. The IR spectral data of these complexes suggest that the metals are coordinated through nitrogen of the imine group, the oxygen of carboxylate ion and the oxygen of the phenolic –OH group which also acts as the bridging ligand. The electronic spectra and magnetic moments of the polychelates shows that octahedral and square planar structure for Ni(II) and Cu(II) complexes respectively. X-ray diffraction studies revealed that polychelates are highly crystalline. The thermal and electrical properties, catalytic activity, structure property relationships are discussed. Further the synthesized polymer was used for metal uptake studies from waste water, which is one of the effective waste water treatment strategies. And also, the polymers and polychelates were investigated for antimicrobial activity with various microorganisms by using agar well diffusion method and the results have been discussed.

Keywords: acyclic compartmental ligands, binucleating ligand, 3-formylsalicylic acid, free radical polymerization, polluting ions, polychelate

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Authors: Messai Amel, Badis Zakaria, Benali-Cherif Nourredine, Dominique Luneaub

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We are interested in molecular polymetallic species having high spin and nuclearities in relation to the field of so call single-molecule magnets (SMMs). The goal is to find a way to synthesis metal clusters which may have application in magnetism and nano sciences. With this purpose, we decided to investigate the coordination chemistry of the Schiff base. Along this way we were able to create cubane-like complexes and elaborate new Single Molecule-Magnets. The idea was to use Schiff base ligands and different metals to generate high nuclear complexes. Complexation of Shiff base with copper (II) has been investigated. Tetra nuclear complex with a cubane like core have been synthesized with (Sciff base), with the same base and cobalt (II) we obtain an other single magnetic complex completely different. In this presentation, we report the synthesis, crystal structure and magnetic properties of the tetranuclear compound (Cu4 L4), and the tetranuclear compound. (Co4L4)

Keywords: cluster-assembled materials, magnetic compounds, Sciff base, cupper, cobalt

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Authors: Emel Yildiz, Nurcan Biçer, Fazilet Aksu, Arash Alizadeh Yegani

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Plants provide the wealth of bioactive compounds, which exert a substantial strategy for the treatment of neurological disorders such as Alzheimer's disease. Recently, a lot of studies have explored the medicinal properties of curcumin, including antitumoral, antimicrobial, anti-inflammatory, antioxidant, antiviral, and anti-Alzheimer's disease effects. Metal complexes of curcumin (1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) were synthesized with Mn(II) and Fe(III). The structures of synthesized metal complexes have been characterized by using spectroscopic and analytic methods such as elemental analysis, magnetic susceptibility, FT-IR, AAS, TG and argentometric titration. It was determined that the complexes have octahedral geometry. The effects of the metal complexes on the disorder of memory, which is an important symptom of Alzheimer's Disease were studied on lab rats with Plus-Maze Tests at Behavioral Pharmacology Laboratory.

Keywords: curcumin, Mn(II), Fe(III), Alzheimer disease, beta amyloid 25-35

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Authors: Hany M. Abd El-Lateef

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Two novel Schiff bases, 5-bromo-2-[(E)-(pyridin-3-ylimino) methyl] phenol (HBSAP) and 5-bromo-2-[(E)-(quinolin-8-ylimino) methyl] phenol (HBSAQ) have been synthesized. They have been characterized by elemental analysis and spectroscopic techniques (UV–Vis, IR and NMR). Moreover, the molecular structure of HBSAP and HBSAQ compounds are determined by single crystal X-ray diffraction technique. The inhibition activity of HBSAP and HBSAQ for carbon steel in 3.5 %NaCl+0.1 M HCl for both short and long immersion time, at different temperatures (20-50 ºC), was investigated using electrochemistry and surface characterization. The potentiodynamic polarization shows that the inhibitors molecule is more adsorbed on the cathodic sites. Its efficiency increases with increasing inhibitor concentrations (92.8 % at the optimal concentration of 10-3 M for HBSAQ). Adsorption of the inhibitors on the carbon steel surface was found to obey Langmuir’s adsorption isotherm with physical/chemical nature of the adsorption, as it is shown also by scanning electron microscopy. Further, the electronic structural calculations using quantum chemical methods were found to be in a good agreement with the results of the experimental studies.

Keywords: carbon steel, Schiff bases, corrosion inhibition, SEM, electrochemical techniques

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Authors: Maha A. Younus, Dhefaf H. Badri, Maha A. Al Abayaji, Taha M. Salih

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Polymer metal complexes of poly vinyl alcohol and Cu (II), Ni (II), Mn (II) and Co (III) were prepared from the reaction of PVA with three different percentages of urea. The compound was characterized by fourier transform infrared spectrometry (FTIR) analysis and differential scanning calorimetric (DSC) Analysis. It has been established that the polymer and its metal complexes showed good activities against nine pathogenic bacteria (Escherichia coli, Klebsiellapneumonae, Staphylococcusaureus, Staphylococcus Albus, Salmonella Typhoid, Pseudomonas Aeruginosa, Shigella Dysentery, Proteus Morgani, Brucella Militensis). The polymer metal complexes show activity higher than that of the free polymer. The increasing activities were in the order (polymer < pol-Mn< pol-Co < pol-Ni ˂ pol-Cu). The ability of these compounds to show antimicrobial properties suggests that they can be further evaluated for medicinal and/or environmental applications.

Keywords: antimicrobial activity, PVA, polymer-metal complex, urea

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Authors: Omoruyi G. Idemudia, Alexander P. Sadimenko

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The need for the development of new sustainable bioactive compounds with unique properties that can become potential replacement for commonly used medicinal drugs has continued to gain tremendous research concerns because of the problems of disease resistant to these medicinal drugs and their toxicity effects. NOS-donor heterocycles are particularly of interest as they have showed good pharmacological activities in the midst of their interesting chelating properties towards metal ions, an important characteristic for transition metal based drugs design. These new compounds have also gained application as dye sensitizers in solar cell panels for the generation of renewable solar energy, as greener water purification polymer for supply and management of clean water and as catalysts which are used to reduce the amount of pollutants from industrial reaction processes amongst others, because of their versatile properties. Di-ketone acylpyrazolones and their azomethine schiff bases have been employed as pharmaceuticals as well as analytical reagents, and their application as transition metal complexes have being well established. In this research work, a new 4-propyl-3-methyl-1-phenyl-2-pyrazolin-5-one-thiosemicarbazone was synthesized from the reaction of 4-propyl-3-methyl-1-phenyl-2-pyrazolin-5-one and thiosemicarbazide in methanol. The pure isolate of the thiosemicarbazone was further reacted with aqueous solutions of palladium and platinum salts to obtain their metal complexes, in an effort towards the discovery of transition metal based synthetic drugs. These compounds were characterized by means of analytical, spectroscopic, thermogravimetric analysis TGA, as well as x-ray crystallography. 4-propyl-3-methyl-1-phenyl-2-pyrazolin-5-one thiosemicarbazone crystallizes in a triclinic crystal system with a P-1 (No. 2) space group according to x-ray crystallography. The tridentate NOS ligand formed a tetrahedral geometry on coordinating with metal ions. Reported compounds showed varying antioxidant free radical scavenging activities against 2, 2-diphenyl-1-picrylhydrazyl DPPH radical at 100, 200, 300, 400 and 500 µg/ml concentrations. The platinum complex have shown a very good antioxidant property against DPPH with an IC50 of 76.03 µg/ml compared with standard ascorbic acid (IC50 of 74.66 µg/ml) and as such have been identified as a potential anticancer candidate.

Keywords: acylpyrazolone, free radical scavenging activities, tridentate ligand, x-ray crystallography

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Authors: V. K. Srivastava

Abstract:

The chemistry of compounds containing transition metals bound to sulfur containing ligands has been actively studied. Interest in these compounds arises from the identification of the biological importance of iron-sulfur containing proteins as well as the unusual behaviour of several types of synthetic metal-sulfur complexes. Metal complexes (C₆H₅)₄P)₂ Pt(Mos₄)₂, (C₆H₅)₄P)₂ Pd(MoS₄)₂, (C₆H₅)₄P)₂ Ni(MoS₄)₂ of bioinorganic relevance were investigated. The complexes [M(M'S₄)₂]²⁻ were prepared with high yield and purity as salts of the variety of organic cations. The diamagnetism and spectroscopic properties of these complexes confirmed that their structures are essentially equivalent with two bidentate M'S₄²⁻ ligands coordinated to the central d⁸ metal in a square planer geometry. The interaction of the complexes with CT-DNA was studied. Results showed that metal complexes increased DNA's relative viscosity and quench the fluorescence intensity of EB bound to DNA. In antimicrobial activities, all complexes showed good antimicrobial activity higher than ligand against gram positive, gram negative bacteria and fungi. The antitumor properties have been tested in vitro against two tumor human cell lines, Hela (derived from cervical cancer) and MCF-7 (derived from breast cancer) using metabolic activity tests. Result showed that the complexes are promising chemotherapeutic alternatives in the search of anticancer agents.

Keywords: anti cancer, biocidal, DNA binding, spectra

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Authors: L. Mallesha, P. Mallu, B. Veeresh

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In the present study, 2, 6-diflurobenzohydrazide and 4-fluorophenylisothiocyanate were used as the starting materials to synthesize 5-phenyl-N3-(4-fluorophenyl)-4H-1, 2, 4-triazole-3, 4-diamine. Further, compound 5-phenyl-N3-(4-fluorophenyl)-4H-1, 2, 4-triazole-3,4-diamine reacted with fluoro substituted benzaldehydes to yield a series of Schiff bases. All the final compounds were characterized using IR, 1H NMR, 13C NMR, MS and elemental analyses. New compounds were evaluated for their antiproliferative effect using the MTT assay method against four human cancer cell lines (K562, COLO-205, MDA-MB231, and IMR-32) for the time period of 24 h. Among the series, few compounds showed good activity on all cell lines, whereas the other compounds in the series exhibited moderate activity.

Keywords: Schiff bases, MTT assay, antiproliferative activity, human cancer cell lines, 1, 2, 4-triazoles

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Authors: Nadia A. Mohamed, Magdy W. Sabaa, Ahmed H. H. El-Ghandour, Marwa M. Abdel-Aziz, Omayma F. Abdel-Gawad

Abstract:

Eighteen carboxymethyl chitosan (CMCh) schiff bases and their reduced derivatives have been synthesized. They were characterized by spectral analyses (FT-IR and H1-NMR) and scanning electron microscopy observation. Their antibacterial activities against Streptococcus pneumoniae (RCMB 010010), Bacillis subtilis (RCMB 010067), as Gram positive bacteria and Escherichia coli (RCMB 010052) as Gram negative bacteria and the antifungal activity against Aspergillus fumigatus (RCMB 02568), Geotricum candidum (RCMB 05097), and Candida albicans (RCMB 05031) were examined using agar disk diffusion method. The results demonstrate how the antibacterial and the antifungal activity are clearly affected by both the nature and position of the substituent groups in the aryl ring of the prepared derivatives. CMCh-4-nitroBenz Schiff base and its reduced form show higher antimicrobial activity comparing with other para substituted derivatives. CMCh-4-nitroBenz Schiff base: 18.3, 17, and 15.6 mm against Bacillis subtilis, Streptococcus pneumonia, and Escherichia coli respectively and 16.2, 17.3, and 16.4 mm against Aspergillus fumigates, Geotricum candidum, and Candida albicans respectively. CMCh-4-nitroBenz reduced form: 19.5, 18.7, and 16.2 mm against Bacillis subtilis, Streptococcus pneumonia, and Escherichia coli respectively and 17.5, 19.5, and 17.4 mm against Aspergillus fumigates, Geotricum candidum, and Candida albicans respectively. Also CMCh-3-bromoBenz show good results; CMCh-3-bromoBenz schiff base: 19.2, 16.9, and 14.6 mm Bacillis subtilis, Streptococcus pneumonia, and Escherichia coli respectively and 18.4, 17.6, and 15.9 mm against Aspergillus fumigates, Geotricum candidum, and Candida albicans respectively.

Keywords: chitosan, schiff base, minimum inhibition concentration, antimicrobial activity

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Authors: Sanja O. Podunavac-Kuzmanović, Lidija R. Jevrić, Strahinja Z. Kovačević

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In last decade, metal-organic complexes have captured intensive attention because of their wide range of biological activities such as antibacterial, antifungal, anticancerous, antimicrobial and antiHIV. Therefore, it is of great importance for the development of coordination chemistry to explore the assembly of functional organic ligands with metal ion and to investigate the relationship between the structure and property. In view of our studies, we reasoned that benzimidazoles complexed to metal ions could act as a potent antibacterial agents. Thus, we have bioassayed the inhibitory potency of benzimidazoles and their metal salts (Co or Ni) against Gram negative bacteria Escherichia coli. In order to validate our in vitro study, we performed in silico studies using molecular docking software’s. The investigated compounds and their metal complexes (Co, Ni) showed good antibacterial activity against Escherichia coli. In silico docking studies of the synthesized compounds suggested that complexed benzimidazoles have a greater binding affinity and enhanced antibacterial activity in comparison with noncomplexed ligands. In view of their enhanced inhibitory properties we propose that the studied complexes can be used as potential pharmaceuticals. This study is financially supported by COST action CM1306 and the project No. 114-451-347/2015-02, financially supported by the Provincial Secretariat for Science and Technological Development of Vojvodina.

Keywords: benzimidazoles, complexes, antibacterial, Escherichia coli, metal

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Authors: Angelo Lanzilotto, Martin Kuss-Petermann, Catherine E. Housecroft, Edwin C. Constable, Oliver S. Wenger

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We recently described the synthesis of a new tetraphenylporphyrinatozinc(II)-conjugated 2,2':6',6"-terpyridine (1) in which the tpy domain enables the molecule to act as a metalloligand. The synthetic route to 1 has been optimized, the importance of selecting a particular sequence of synthetic steps will be discussed. Three homoleptic complexes have been prepared, [Zn(1)₂]²⁺, [Fe(1)₂]²⁺ and [Ru(1)₂]²⁺, and have been isolated as the hexafluoridophosphate salts. Spectroelectrochemical measurements have been performed and the spectral changes ascribed to redox processes are partitioned on either the porphyrin or the terpyridine units. Compound 1 undergoes a reversible one-electron oxidation/reduction. The removal/gain of a second electron leads to a further irreversible chemical transformation. For the homoleptic [M(1)₂]²⁺ complexes, a suitable potential can be chosen at which both the oxidation and the reduction of the {ZnTPP} core are reversible. When the homoleptic complex contains a redox active metal such as Fe or Ru, spectroelectrochemistry has been used to investigate the metal to ligand charge transfer (MLCT) transition. The latter is sensitive to the oxidation state of the metal, and electrochemical oxidation of the metal center suppresses it. Detailed spectroelectrochemical studies will be presented.

Keywords: homoleptic complexes, spectroelectrochemistry, tetraphenylporphyrinatozinc(II), 2, 2':6', 6"-terpyridine

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