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Öğe The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts(Elsevier Science Sa, 2021) Kaloglu, Murat; Slimani, Ichraf; Ozdemir, Namik; Gurbuz, Nevin; Hamdi, Naceur; Ozdemir, IsmailIn this study, a series of air- and moisture-stable imidazolidin-2-ylidene-based new palladium complexes with the general formula [PdX2(NHC)(Py)] were synthesized (NHC = N-heterocyclic carbene, Py = pyridine, X = Cl or I). The structures of the palladium complexes were characterized by different techniques such as H-1 NMR, C-13 NMR, FT-IR spectroscopy and elemental analysis. The more detailed structural characterization of one of the palladium complex was determined by single-crystal X-ray diffraction study. The catalytic activities of all palladium complexes were tested in the direct arylation of five-membered aromatic N-heterocycles such as 3,5-dimethylisoxazole and 1-methyl-1H-pyrrole-2-carboxaldehyde with (hetero)aryl bromides in presence of 1 mol% catalyst loading at 120 degrees C. Desired products were obtained in moderate to good yields. (C) 2021 Elsevier B.V. All rights reserved.Öğe Experimental and Quantum Mechanical Investigation of N-heterocyclic Carbene Palladium Complex: Synthesis and Antibacterial Activity(Biointerface Research Applied Chemistry, 2022) Slimani, Ichraf; Zouaghi, Mohamed Oussama; Jebli, Nejib; Youssef, Arfaoui; Ozdemir, Namik; Ozdemir, Ismail; Gurbuz, NevinIn this study, we report the synthesis, characterization, and biological activity of Pd-NHC-PEPPSI complex 2a. Further confirmations of structural details were provided by a single-crystal X-ray. A single crystal of 2a shows that the coordination geometry around Pd slightly distorted square-planar geometry. Intermolecular interactions have been studied through the NBO analyses. Structural parameters and spectroscopic properties of the complexes are well interpreted by DFT and TD-DFT calculations. Moreover, the complex 2a showed a remarkable antimicrobial effect against Micrococcus luteus LB 14110mm, Listeria monocytogenes ATCC 19117, Salmonella typhimurium ATCC 14028, Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa, and Candida albicans.Öğe Novel N-Heterocyclic Carbene Silver(I) Complexes: Synthesis, Structural Characterization, Antimicrobial and Cytotoxicity Potential Studies(Soc Brasileira Quimica, 2020) Slimani, Ichraf; Chakchouk-Mtibaa, Ahlem; Mellouli, Lotfi; Mansour, Lamjed; Ozdemir, Ismail; Gurbuz, Nevin; Hamdi, NaceurIn this study, a series of unsymmetrical N,N-disubstituted benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) (2a-2j) and their Ag-I complexes. Their structures were characterized by elemental analyses, H-1 and C-13 nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy techniques. Further, both the salts and their silver(I)-NHC complexes have been evaluated for their potential antibacterial properties against a panel of bacterial strains namely, Micrococcus luteus, Listeria monocytogenes, Salmonella Typhimurium, Staphylococcus aureus and Pseudomonas aeruginosa. The results show that silver complexes are effective against Salmonella Typhimurium, Listeria monocytogenes, and Micrococcus luteus with moderate to high activity, and their minimum inhibitory concentrations ranging from 0.0034 to 1.26 mg mL(-1). In addition, the benzimidazoles salts 2a-2j and silver-NHC complexes 3a-3j were screened for their antitumor activity. Complex 3e exhibited the highest antitumor effect with half-maximal inhibitory concentration (IC50) value of 4.2 mu g mL(-1) against MCF-7.Öğe Rhodium(I) complexes with N-heterocyclic carbene ligands: synthesis, biological properties and catalytic activity in the hydrosilylation of aromatic ketones(Taylor & Francis Ltd, 2021) Hamdi, Naceur; Slimani, Ichraf; Mansour, Lamjed; Alresheedi, Faisal; Ozdemir, Ismail; Gurbuz, NevinNew rhodium(I) N-heterocyclic carbene (NHC) complexes 3a-f were synthesized in good yields by the reactions of rhodium dimer [Rh(OMe)(cycloocta-1,5-diene:COD)](2) with benzimidazolium salts 2a-f in tetrahydrofuran. All the complexes were characterized by IR, H-1-NMR, and C-13-NMR spectroscopy, DART-TOF mass spectrometry (for 3b, 3d and 3f) and elemental analysis. All complexes were used as catalysts in the hydrosilylation of acetophenone derivatives with triethylsilane at 80 degrees C for 1 h. These Rh(I) NHC showed good catalytic performance for the hydrosilylation of acetophenone derivatives by using 1 mol % of the rhodium complexes. In addition the new rhodium(I) NHC complexes were tested against MCF7 and MDA-MB-231 cancer cells, Micrococcus luteus LB 14110, Listeria monocytogenes ATCC 19117, Salmonella Typhimurium ATCC 14028, Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa and Candida albicans microorganisms. The synthesized rhodium(I) NHC complex 3f was found the most active against MCF7 cancer cells (half-growth inhibition concentration (IC50) = 0.3 mu g mL(-1)), as well as the most potent antimicrobial against L. monocytogenes ATCC 19117 (inhibition zone (IZ) = 29 mm). Moreover, the antioxidant activity determination of these complexes was studied with the DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) and compared with gallic acid and butylated hydroxytoluene.Öğe Rhodium(i) N-heterocyclic carbene complexes: synthesis and cytotoxic properties(Royal Soc Chemistry, 2021) Slimani, Ichraf; Sahin-Bolukbasi, Serap; Ulu, Mustafa; Evren, Enes; Gurbuz, Nevin; Ozdemir, Ilknur; Hamdi, NaceurRhodium(i) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these types of complexes. A series of benzimidazolium salts and their [RhCl(NHC)(COD)] complexes were synthesized. The obtained complexes were synthesized and characterized by elemental analysis, FT-IR, H-1 and C-13 NMR. All compounds were screened for in vitro cytotoxic activities against a panel of human cancer cells (HT-29 colon, Ishikawa endometrial, and U-87 glioblastoma) using the MTT assay for 48 h of incubation time. Mouse fibroblast cells (L-929) were used as healthy cells. Complexes had exhibited significantly higher cytotoxic activity towards cancer cells than their ligands and complex 2b showed the most selective cytotoxic activity against HT-29 cancer cells (SI;7.05) and Ishikawa cancer cells (SI; more than 9.8). The complexes showed strong in vitro cytotoxic activity against cancer cells, with IC50 values of lower than 10 mu M (except 2a against HT-29 (12.8 mu M) and 2b against U-87 (11.1 mu M)). All complexes (2a-d) showed the highest in vitro cytotoxic activity against Ishikawa endometrial cancer cells with IC50 values of 2.93 +/- 0.06, <1, 2.60 +/- 0.05, and 2.85 +/- 0.06 mu M, respectively. Complexes were found to be highly cytotoxic against HT-29, Ishikawa, and U-87 cancer cells compared to the anticancer agents, cisplatin and 5-FU.Öğe Synthesis, characterization and catalytic activity of PEPPSI-type palladium-NHC complexes(Elsevier Science Sa, 2021) Slimani, Ichraf; Mansour, Lamjed; Ozdemir, Ismail; Gurbuz, Nevin; Hamdi, NaceurEight benzimidazolium salts (2a-h) with two nitrogen atoms substituted by various alkyl groups have been synthesized in high yields. The benzimidazolium salts were readily converted into the corresponding PEPPSItype palladium-NHC complexes (PEPPSI = pyridine-enhanced precatalyst preparation, stabilization, and initiation) (3a-h). The structures of all compounds were characterized by H-1 NMR, C-13 NMR, and IR spectroscopy as well as by elemental analysis techniques, which support the proposed structures. The catalytic activity of the PEPPSI-type palladium-NHC complexes was evaluated with respect to the direct C5-arylation of 2-substituted heteroaryl derivatives (thiophene, furan and thiazole) with various aryl bromides. This arylation occurs efficiently and selectively at the C5-position of the 2-substituted thiophene, furan and thiazole derivatives.Öğe Synthesis, characterization, biological determination and catalytic evaluation of ruthenium(ii) complexes bearing benzimidazole-based NHC ligands in transfer hydrogenation catalysis(Royal Soc Chemistry, 2020) Slimani, Ichraf; Chakchouk-Mtibaa, A.; Mansour, L.; Mellouli, L.; Ozdemir, I; Gurbuzd, Nevin; Hamdi, NaceurA new series of ruthenium(ii) N-heterocyclic carbene complexes has been synthesized via transmetalation. These complexes are easily handled in very good yields via synthesis of silver-NHC complexes and subsequent reaction with [RuCl2(p-cymene)](2) in dichloromethane (DCM) under argon atmosphere. The new ruthenium(ii)-NHC complexes were applied to transfer hydrogenation of ketone derivatives using 2-propanol as a hydrogen source and KOH as a co-catalyst. The results show that the corresponding alcohols could be obtained in good yield with high catalyst activity (up to 76%) under mild conditions. All new compounds were characterized by spectroscopic and analytical methods. The antibacterial activities of the corresponding ruthenium(ii)-NHC complexes 4a-i were tested against positive and negative bacteria using the agar dilution procedure and their IC50 values have been determined. A cytotoxicity study of the ruthenium(ii)-NHC complexes 4 was performed against the two human cancer cell lines MDA-MB-231 and MCF-7. In addition, the scavenging activity of the synthesized complexes for the DPPH radical was also determined.Öğe Synthesis, crystal structures, DFT calculations, and catalytic application in hydrosilylation of acetophenone derivatives with triethylsilane of novel rhoduim-N-heterocyclic carbene (NHCs) complex(Elsevier, 2022) Hassen, Sabri; Zouaghi, Mohamed Oussama; Slimani, Ichraf; Arfaoui, Youssef; Ozdemir, Namik; Ozdemir, Ismail; Gurbuz, NevinN-Heterocylic carbenes (NHCs) and their role as universal spectator ligands in transition metal compounds have recently sparked a wide interest in the broader field of green chemistry because of their astounding catalytic properties in reactions involving organic synthesis. In this study, a new rhodium based complex has been developed that incorporate an N-heterocyclic carbene ligand. This rhodium(I) N-heterocyclic carbene complex was characterized fully and the solid-state single crystal X-ray structure of the complex was discussed. Single-crystal X-ray diffraction analysis indicates that this complex crystallizes in the centrosymmetric space group Pbca of the orthorhombic system. The carbene complex exhibits the same general structural motif with slightly distorted square-planar geometry. The ground state geometry of the complex was optimized using density functional theory (DFT) at mixed double zeta basis set, 6-31G(d) for H, C, N, O and Cl and LANL2DZ for Rh. The presence of the different functional groups and the nature of their vibrations were identified by the experimental and theoretical infrared spectra. The optical properties of the studied complex were determined experimentally using UV-visible and photoluminescence techniques in solid state and theoretically using the TD-DFT method. Hirshfeld surface analysis employing 3D molecular surface contours and 2D fingerprint plots has been used to analyze intermolecular interactions present in the solid state. The utility of this complex as catalyst precursor for in the hydrosilylation of acetophenone derivatives with triethylsilane at 80 & DEG;C for 2 h using 1 mol% of the rhodium complexes was studied.The new rhodium(I) N-heterocyclic carbene complex 3 were also tested against MCF7 and MDA-MB-231 cancer cells, as well as Micrococcus luteus LB 14,110, Listeria monocytogenes ATCC 19,117, S. Typhimurium ATCC 14,028, Staphylococcus aureus ATCC 6538, Pseudomonas aeruginosa, and Candida albicans microorganisms. (c) 2022 Elsevier B.V. All rights reserved.Öğe Synthesis, structural characterization of silver(I)-NHC complexes and their antimicrobial, antioxidant and antitumor activities(Elsevier, 2020) Slimani, Ichraf; Mansour, Lamjed; Abutaha, Nael; Harrath, Abdel Halim; Al-Tamimi, Jameel; Gurbuz, Nevin; Ozdemir, ITo prepare a novel series of silver (I) complexes, the interaction of benzimidazolium salts having their two nitrogen atoms substituted by bulky groups with Ag2O in DMF has been carried out. Their structures were characterized by elemental analyses, H-1 NMR, C-13 NMR and IR spectroscopy techniques. Further, the antibacterial properties of both the salts and their silver(I)-NHC complexes were tested against positive and negative bacteria using the agar dilution procedure. The results show that silver complexes are effective against Salmonella Typhimurium, Listeria monocytogenes, and Micrococcus luteus with moderate to high activity, and their minimum inhibitory concentrations ranging from 0.0024 to 1.25 mg/ml. Moreover, the antioxidant activity determination of these compounds were studied with the DPPH, and compared with (gallic acid GAand butylatedhydroxytoluene BHT ). They exhibited significant antioxidant activities. In addition, the of benzimidazoles salts 2a-j and silver-NHC complexes 3a-j were screened for their antitumor activity. The highest antitumor activity was observed for 3e and 3d Complexes and they exhibited IC50 values 6.85 mu g/mL against MCF-7 and 10.75 mu g/mL against T47D, respectively. (C) 2019 The Authors. Published by Elsevier B.V. on behalf of King Saud University.
