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    Electrochemical reduction of NAP on the glassy carbon electrodes modified with aromatic diazonium salts
    (Bentham Science Publ Ltd, 2008) Sadikoglu, Murat; Solak, Ali O.; Isiklan, Muhammet; Kilic, Zeynel
    The electrochemical reduction of 4-{[(1E)-(2-hydroxynaphthyl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one (NAP) was studied by using cyclic voltammetry in acetonitrile media at a glassy carbon (GC) and modified GC electrodes. The GC electrodes were grafted by electrochemical reduction of diazonium salts of various organic molecules. GC surfaces modified with anthraquinone, p-nitrophenyl, p-aminophenyl, p-amino-N,N-dimethylphenyl and p-methoxyphenyl radicals were used to investigate the reduction behaviors of NAP. The effect of the modified glassy carbon electrodes on the reduction of NAP was studied as being related to the role of the electron donor or the electron acceptor groups on the phenyl ring attached to the surface. The compound NAP shows two reduction peaks in a cyclic voltammogram. These peaks were observed at -2.1 V and-2.7 V on the GC electrode surface. Also, the reduction peaks of NAP were obtained for all the modified electrodes studied. The p-methoxyphenyl modified GC electrode showed a significant increase in the rate of electron transfer at the reduction of NAP. The kinetics and the mechanism of the electrode process were simulated and some parameters were calculated using BAS Digi-Sim (R) software.
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    Structural and computational characterization of 4 ',4 ',6 ',6 '-tetrachloro-3-(2-methoxyethyl)-3H,4H-spiro-1,3,2-benzoxaza phosphinine-2,2 '-[1,3,5,2,4,6]triazatriphosphinine
    (Elsevier, 2016) Isiklan, Muhammet; Yildirim, Erdem Kamil; Atis, Murat; Sonkaya, Omer; Cosut, Bunyemin
    In this study a new monospirocyclic phosphazene derivative, 4',4',6',6'-tetrachloro-3-(2-methoxyethyl)3H,4H-spiro [1,3,2-benzoxazaphosphinine-2,2'- [1,3,5,2,4,6] triazatriphosphinine] (SP1) was synthesized from the reaction of hexachlorocyclotriphosphazene (N3P3CI6) with N/0 donor-type, 2-{[(2-Metoxyethyl) amino]methylphenol. The structural investigations of the compound were verified by elemental analyses, MS, FFIR, 1H, 13C, 11 --P NMR spectroscopy and the single crystal X-ray diffraction analysis. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional method (DFT) using 6-311++G (d, p) basis set. The complete assignments of all vibrational modes were performed on the basis of the total energy distributions (TED). Isotropic chemical shifts (31P, 1H and 13C NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. Theoretical calculations of bond parameters, harmonic vibration frequencies and nuclear magnetic resonance are in good agreement with experimental results. The electrophilic and nucleophilic attack centers in SP1 were predicted with the local softness values (sit, and si) of individual atoms and it is confirmed that P atoms of the PCl2 groups are nucleophilic attack centers. (C) 2016 Elsevier B.V. All rights reserved.
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    Synthesis, structural characterization, and cytotoxic activity of new spirocyclic octachlorocyclotetraphosphazenes
    (Taylor & Francis Ltd, 2016) Isiklan, Muhammet; Sayin, Levent; Sonkaya, Omer; Hokelek, Tuncer; Turk, Mustafa; Oguztuzun, Serpil
    Octachlorocyclotetraphosphazene, N4P4Cl8, (1) was reacted with N, N-dibenzylethylenediamine to synthesize partially substituted monospiro- (2), dispiro- (5) and tetraspirocyclotetraphosphazene (8) derivatives. The reactions of 2 and 5 with excess pyrrolidine and morpholine produced fully substituted pyrrolidino (3 and 6) and morpholino (4 and 7) spirocyclotetraphosphazenes. The structures of the compounds were determined with 1D (H-1, C-13, P-31, and DEPT) NMR, 2D (HSQC) NMR, ESI-MS, FTIR, and elemental analysis. The solid-state structures of 6 and 7 were examined by X-ray crystallography. In 7, intramolecular C-H...O hydrogen bonds link the molecules into centrosymmetric dimmers. The cytotoxic activity of all the compounds against human cervix carcinoma cell lines (HeLa) was investigated. The study showed that these compounds exert limited cytotoxic, apoptotic and necrotic effects on HeLa cancer cell lines.