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Öğe Direct arylation of heteroarenes by PEPPSI-type palladium-NHC complexes and representative quantum chemical calculations for the compound which the structure was determined by X-ray crystallography(Taylor & Francis Ltd, 2019) Sahin, Neslihan; Serdaroglu, Goncagul; Dusunceli, Serpil Demir; Tahir, Muhammad Navaz; Arici, Cengiz; Ozdemir, IsmailIn this study, we synthesized five new PEPPSI-type Pd-NHC complexes with high yields around 78-83%. The structures of all complexes were characterized by FT-IR, H-1 NMR, and C-13{H-1} NMR spectroscopies. Further, the structure of 2c was determined by X-ray crystallography. The single-crystal structure of 2c shows that coordination geometry around Pd is distorted square planar. The Pd-NHC complexes were efficient catalysts for the direct C5-arylation of 2-n-butylthiazole, 2-n-butylfuran, and 2-n-butylthiophene with various aryl-bromides and showed high catalytic activity for arylation reaction using only 1 mol% catalyst loading at 130 degrees C for 1 h. The conversions for substrates containing electron-withdrawing groups were higher than for substituents containing electron-donating groups. In order to evaluate the catalytic activity of the complexes, representative electronic and spectroscopic simulations by DFT method have been performed for 2c. NBO analysis has revealed that the strongest interaction contributing to the lowering of the molecular stabilization energy for 2c is predicted as pi(C11-N27) -> pi*(N26-C28) with E-(2) = 73.93 kcal mol(-1). In addition, FMO analysis has implied that 2c is more chemically reactive because of its lower energy gap value. According to the other quantum chemical parameters, 2c is softer, better electrophile and has more charge-transfer capability than 1c.Öğe Novel Ag(I)-NHC complex: synthesis, in vitro cytotoxic activity, molecular docking, and quantum chemical studies(Walter De Gruyter Gmbh, 2022) Serdaroglu, Goncagul; Sahin, Neslihan; Sahin-Bolukbasi, Serap; Ustun, ElvanThe importance of organometallic complexes in cancer biology has attracted attention in recent years. In this paper, we look for the in vitro cytotoxic capability of novel benzimidazole-based N-heterocyclic carbene (NHC) precursor (1) and its Ag(I)-NHC complex (2). For this purpose, these novel Ag(I)-NHC complex (2) was characterized by spectroscopic techniques (H-1, C-13{H-1} nuclear magnetic resonance (NMR), and Fourier-transform infrared spectroscopy (FT-IR)). Then, in vitro cytotoxic activities of NHC precursor (1) and Ag(I)-NHC complex (2) were investigated against MCF-7, MDA-MB-231 human breast, DU-145 prostate cancer cells, and L-929 healthy cells using MTT assay for 24, 48, and 72 h incubation times. Ag(I)-NHC complex (2) showed promising in vitro cytotoxic activity against all cell lines for three incubation times, with IC50 values lower than 5 mu M. It was also determined that (NHC) precursor (1) were lower in vitro cytotoxic activity than Ag(I)-NHC complex (2) against all cell lines. Selectivity indexes (SIs) of Ag(I)-NHC complex (2) against cancer cells were found higher than 2 for 24 and 48 h incubation time. Besides, the electronic structure and spectroscopic data of the newly synthesized precursor and its Ag-complex have been supported by density functional theory (DFT) calculations and molecular docking analysis. After, the anticancer activity of these compounds has been discussed considering the results of the frontier molecular orbital analysis. We hope that the obtained results from the experiments and computational tools will bring a new perspective to cancer research in terms of supported by quantum chemical calculations.Öğe PEPPSI type complexes: Synthesis, x-ray structures, spectral studies, molecular docking and theoretical investigations(Pergamon-Elsevier Science Ltd, 2021) Serdaroglu, Goncagul; Sahin, Neslihan; Ustun, Elvan; Tahir, Muhammad Navaz; Arici, Cengiz; Gurbuz, Nevin; Ozdemir, IsmailIn this work, three novel potent benzimidazolium-derived PEPPSI type palladium complexes, namely dichloro[1-allyl-3-benzylbenzimidazole-2-ylidene]pyridine palladium(II) (1), dichloro[1-allyl-3-(1-naphthylmethyl)benzimidazole-2-ylidene]pyridine palladium(II) (2) and dichloro[1-allyl-3-(9-anthrylmethyl)benzimidazole-2-ylidene]pyridine palladium(II) (3), were synthesized and characterized by single X-ray crystallography, FT-IR and NMR spectroscopy. The results were compared with the relevant calculated data. After structural and spectroscopic determination, the performance of the global reactivity behavior of these derivatives was evaluated by quantum chemical parameters (QCP) obtained from DFT/B3LYP and HF methods utilized with the 6-311 g**/LANL2DZ basis set. Next, NBO analyses were conducted to enlighten the possible interactions that occur for each derivative and this revealed that the main role in the lowering of the stabilization energies of all the derivatives was sourced from n -> pi* and pi -> pi* interactions. Finally, all the complexes were analyzed for their anticancer potential by the molecular docking method with VEGFR (vascular endothelial growth factor receptor), thioredoxin reductase, breast cancer and the dodecamer structure of DNA. (C) 2021 Elsevier Ltd. All rights reserved.Öğe Synthesis, in vitro anticancer activities, and quantum chemical investigations on 1,3-bis-(2-methyl-2-propenyl)benzimidazolium chloride and its Ag(I) complex(Sage Publications Ltd, 2021) Serdaroglu, Goncagul; Sahin-Bolukbasi, Serap; Barut-Celepci, Duygu; Sevincek, Resul; Sahin, Neslihan; Gurbuz, Nevin; Ozdemir, Ismail1,3-Bis-(2-methyl-2-propenyl)benzimidazolium chloride and its Ag(I) complex are synthesized and the structures are elucidated using spectroscopies techniques. The molecular and crystal structures of the benzimidazolium salt are confirmed by X-ray crystallography. The molecular geometries of the benzimidazolium and its Ag(I) salt are analyzed using the B3LYP functional with the 6-311+G(d,p)/LANL2DZ basis set. The observed Fourier transform infrared and nuclear magnetic resonance isotropic shifts are compared with the calculated values. Besides, the quantum chemical identifiers, significant intramolecular interactions, and molecular electrostatic potential plots are used to show the tendency/site of the chemical reactivity behavior. The three-dimensional Hirshfeld surfaces and the associated two-dimensional fingerprint plots are applied to obtain an insight into the behavior of the interactions in the crystal. Both compounds are tested for their in vitro anticancer activities against DU-145 and MCF-7 cancer cells and L-929 non-cancer cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.
