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Öğe 1,3-Bis(3-phenylpropyl)-1H-1,3-benzimidazole-2(3H)-selone(Wiley-Blackwell, 2011) Akkurt, Mehmet; Yilmaz, Ulku; Kucukbay, Hasan; Buyukgungor, OrhanThe title molecule, C25H26N2Se, has mirror symmetry, with the mirror plane passing through the atoms of the C=Se bond and the mid-points of the two C-C bonds of the benzene ring of the benzimidazole group. The dihedral angle between the benzimidazole ring system and the phenyl ring is 71.62 (14)degrees.Öğe 1,3-Bis(3-phenylpropyl)-1H-benzimidazol-3-ium-2-carbodithioate(Wiley-Blackwell Publishing, Inc, 2009) Akkurt, Mehmet; Yilmaz, Ulku; Kucukbay, Hasan; Gencaslan, Mustafa; Buyukgungor, OrhanThe title compound, C(26)H(26)N(2)S(2), was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidine-2-ylidene] and CS(2) in toluene. The molecular structure is composed of a benzimidazole ring system with two phenylpropyl substituents and a dithiocarboxylate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) angstrom, and makes dihedral angles of 72.72 (10) and 27.62 (12)degrees, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)degrees. The molecular packing is stabilized by a C-H center dot center dot center dot S intermolecular hydrogen-bonding interaction and a C-H center dot center dot center dot pi interaction between a benzene H atom and the phenyl ring of a neighbouring molecule.Öğe 1,3-Bis(3-phenylpropyl)-1H-benzimidazole-2(3H)-tellurone(Blackwell Publishing, 2008) Yalcin, Serife Pinar; Akkurt, Mehmet; Yilmaz, Uelkue; Kucukbay, Hasan; Buyukgungor, OrhanThe title compound, C25H26N2Te, was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidin-2-ylidene] and Te in a toluene solution. The molecule possesses a twofold rotation axis passing through the Te atom and the center of the benzimidazole ring system. The benzimidazole ring system makes an angle of 67.9 (4) with the phenyl rings.Öğe 1,3-bis(3-phenylpropyl)benzimidazolium bromide monohydrate(Int Union Crystallography, 2008) Akkurt, Mehmet; Karaca, Selvi; Yilmaz, Ulku; Kucukbay, Hasan; Buyukgungor, OrhanIn the title compound, C25H27N2+center dot Br-center dot H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) angstrom. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)degrees with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)degrees. In the crystal structure, there are C-H center dot center dot center dot O hydrogen bonds, a C H center dot center dot center dot pi interaction between a phenyl H atom and the phenyl ring of a neighbouring molecule, and pi-pi interaction [3.512 (3) angstrom] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent molecule.Öğe 1,3-Difurfurylbenzimidazolium chloride monohydrate(Wiley-Blackwell, 2009) Akkurt, Mehmet; Sireci, Nihat; Deniz, Selma; Kucukbay, Hasan; Buyukgungor, OrhanThe title compound, C17H15N2O2+center dot Cl-center dot H2O, was synthesized from benzimidazole and furfryl chloride in dimethylformamide. The cationic benzimidazolium ring is connected to two furan rings via methylene bridges. The furan rings make dihedral angle of 79.09 (18)degrees with respect to each other, and make dihedral angles of 73.92 (12) and 72.58 (13)degrees with respect to the benzimidazole ring. O-H center dot center dot center dot Cl, C-H center dot center dot center dot O and C-H center dot center dot center dot Cl hydrogen bonds and C-H center dot center dot center dot pi interactions contribute to the stabilization of the crystal structure. Furthermore, there is a pi-pi interaction between adjacent five- and six-membered rings of the benzimidazole groups [centroid-centroid distance = 3.5305 (8) angstromÖğe 1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride monohydrate(Wiley-Blackwell, 2010) Akkurt, Mehmet; Celik, Ismail; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanThe title compound, C(18)H(23)N(2)Si(+)center dot Cl(-)center dot H(2)O, was synthesized from 1-[(trimethylsilyl)methyl]benzimidazole and benzyl chloride in dimethylformamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) angstrom, and makes an angle of 74.80 (12)degrees with the phenyl ring. The crystal packing is stabilized by O-H center dot center dot center dot Cl, C-H center dot center dot center dot Cl, C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions between symmetry-related molecules together with pi-pi stacking interactions between the imidazolium and benzene rings [centroid-centroid distance = 3.5690 (15) angstrom] and between the benzene rings [centroid-centroid distance = 3.7223 (14) angstrom].Öğe 1-cyclohexylmethyl-3-methyl-2-[(phenyl-imino)(sulfido)methyl]benzimidazolium(Int Union Crystallography, 2008) Akkurt, Mehmet; Karaca, Selvi; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanIn the zwitterionic title compound, C22H25N3S, the benzimidazole ring system makes a dihedral angle of 55.69 (11) degrees with the phenyl ring. In the crystal structure, inter- and intramolecular C-H center dot center dot center dot S interactions occur.Öğe 1-{[Dimethyl(phenyl) silyl] methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate(Int Union Crystallography, 2012) Akkurt, Mehmet; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanThe title compound, C24H27N2Si+center dot Br-center dot H2O, was synthesized from 1-(dimethylphenylsilylmethyl)-1H-benzimidazole and (2-bromoethyl) benzene in dimethylformamide. The benzimidazole ring system is nearly planar, with a maximum deviation of 0.015 (5) angstrom, and forms dihedral angles of 73.0 (3) and 39.6 (2)degrees, with the phenyl rings. In the crystal, molecules are linked by O-H center dot center dot center dot Br, C-H center dot center dot center dot Br and C-H center dot center dot center dot O hydrogen bonds. In addition, the structure features pi-pi stacking interactions, with a face-to-face separation of 3.644 (3) angstrom between parallel benzimidazole ring systems.Öğe N-Alkylation and N,C-Dialkylation of Amines with Alcohols in the Presence of Ruthenium Catalysts with Chelating N-Heterocyclic Carbene Ligands(Amer Chemical Soc, 2015) Sahin, Zeynel; Gurbuz, Nevin; Ozdemir, Ismail; Sahin, Onur; Buyukgungor, Orhan; Achard, Mathieu; Bruneau, ChristianA series of new benzimidazolium salts and ruthenium(II) complexes containing chelating N-heterocyclic carbenes (NHCs) functionalized with a benzylic group and an acetal group were prepared. All of the synthesized compounds were characterized by elemental analysis and NMR spectroscopy, and the molecular structures of 2c and 2d were determined by X-ray crystallography. All of the,complexes were tested in the alkylation of cyclic amine derivatives with alcohols and showed excellent activity in this reaction. Cyclic amines were alkylated with primary and heteroaromatic alcohols. The Ru-NHC Complexes also catalyzed N,C3-dialkylation of cyclic amines.Öğe Novel ruthenium(II)-N-heterocyclic carbene complexes; synthesis, characterization and catalytic application(Elsevier Science Sa, 2015) Yasar, Sedat; Karaca, Emine Ozge; Sahin, Caglar; Ozdemir, Ismail; Sahin, Onur; Buyukgungor, OrhanThe synthesis of highly active ruthenium(II) catalyst based on N-heterocyclic carbene (NHC) bearing alkyl and aryl groups is reported. The 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 N-2 condition. All new compounds were characterized by LC-MSMS, elemental analysis, NMR spectroscopy and X-ray diffraction. With the development of a more efficient catalytic system for transfer hydrogenation of aryl ketones and aldehydes in mind, the catalytic performance of the Ru-NHC complexes for transfer hydrogenation was investigated. (c) 2015 Elsevier B.V. All rights reserved.Öğe Palladium Complexes with Tetrahydropyrimidin-2-ylidene Ligands: Catalytic Activity for the Direct Arylation of Furan, Thiophene, and Thiazole Derivatives(Amer Chemical Soc, 2015) Karaca, Emine Ozge; Gurbuz, Nevin; Ozdemir, Ismail; Doucet, Henri; Sahin, Onur; Buyukgungor, Orhan; Cetinkaya, BekirThe synthesis and characterization of novel 1,3-benzyl-3,4,5,6-tetrahydropyrimidin-2-ylidene-based N-hetero-cyclic carbene palladium(II) complexes (1a-d) were described. The crystal structure of trans-dichlorobis[1,3-bis(4-methylbenzyl)-3,4,5,6-tetrahydropyrimidin-2-ylidend- palladium(II) was presented. Pd(II) complexes 1a-d were tested as catalysts in the direct C5 or C2 arylation of furans, thiophenes, and thiazoles, with various aryl bromides at 150 degrees C for 1 h. These complexes exhibited moderate to high catalytic activities under the given conditions.Öğe Palladium N-heterocyclic carbene complexes: Synthesis, characterization and catalytic properties in amination(Elsevier Science Sa, 2010) Ozdemir, Ismail; Demir, Serpil; Sahin, Onur; Buyukgungor, Orhan; Cetinkaya, BekirTransmetalation has proved to be a promising procedure to obtain NHC-metal complexes, which typically involves treatment of the imidazolium salt with Ag2O to form the Ag-NHC complex, followed by transmetalation to a species such as [PdCl2(CH3CN)(2)] gave the palladium complex in which the N-heterocyclic carbene was bound to the metal center. New bis(NHC)-Pd complexes were synthesized and characterized by elemental analysis, H-1 NMR, C-13 NMR, and IR spectroscopy. The crystal and molecular structure of the trans-dichlorobis{1-(2,3,5,6-tetramethylbenzyl)-3-(2,3,4,5,6-pentamethylbenzyl)imidazolidin-2-yliden}palladium(II) complex was determined by single-crystal X-ray diffraction. The activity of the Pd(II) complexes in the coupling reaction of anilines or amines with bromobenzene was investigated. A preliminary catalytic study showed that these bis(NHC)-Pd complexes were highly active in the direct synthesis of triarylamines and secondary amines in a single step. (C) 2010 Elsevier B.V. All rights reserved.Öğe Preparation of a series of Ru(II) complexes with N-heterocyclic carbene ligands for the catalytic transfer hydrogenation of aromatic ketones(Royal Soc Chemistry, 2012) Gurbuz, Nevin; Ozcan, Emine Ozge; Ozdemir, Ismail; Cetinkaya, Bekir; Sahin, Onur; Buyukgungor, OrhanThe reaction of [RuCl2(p-cymene](2) with Ag-N-heterocyclic carbene (NHC) complexes yields a series of [(p-cymene) Ru(NHC)] complexes (2a-f). All synthesised compounds were characterized by elemental analysis, NMR spectroscopy and the molecular structure of 2a was determined by X-ray crystallography. All complexes have been tested as catalysts for the transfer hydrogenation of aromatic ketones, showing excellent activity in this reaction.Öğe Synthesis and Catalytic Activity of Novel Benzimidazolinylidene-Ruthenium(II) Complexes(Georg Thieme Verlag Kg, 2010) Demir, Serpil; Ozdemir, Ismail; Sahin, Onur; Cetinkaya, Bekir; Buyukgungor, OrhanThe reaction of [RuCl2(p-cymene)](2) with 1,3-dialkyl-benzimidazolium salts 1a-d in the presence of a small excess of cesium carbonate yields chelated eta(6)-arene, eta(1)-carbene ruthenium complexes 2a-d. All compounds were characterized by elemental analysis, NMR spectroscopy and the molecular structures of two of the complexes were determined by X-ray crystallography. The catalytic activity of RuCl2(eta(6)-arene, eta(1)-benzimidazolinylidene) complexes was evaluated in the direct arylation of 2-phenylpyridine with bromobenzene derivatives.Öğe Synthesis and characterization of substituted benzimidazole Co(II), Fe(II), and Zn(II) complexes and structural characterization of dichlorobis{1-[2-(1-piperidinyl)ethyl]-1H-benzimidazole-K N3} zinc(II)(Tubitak Scientific & Technological Research Council Turkey, 2015) Kucukbay, Hasan; Yilmaz, Ulku; Akkurt, Mehmet; Buyukgungor, OrhanThe Co(II), Fe(II), and Zn(II) complexes of 1-(3-phenyl)propylbenzimidazole (PPBI), 5-nitro-1-(3-phenyl) propylbenzimidazole (PPNBI), 1-[2-(4-morpholinyl)ethyl]benzimidazole (MEBI), 1-[2-(1-piperidinyl)ethyl]benzimidazole (PEBI), and 5-nitro-1-[2-(1-piperidinyl)ethyl]benzimidazole (PENBI) were synthesized and characterized by H-1 NMR, C-13 NMR, and elemental analyses. The magnitudes of the magnetic moments for paramagnetic complexes were between 4.07 and 5.11 B.M. Moreover, the crystal structure of dichlorobis{1-[2-(1-piperidinyl)ethyl]-1 H-benzimidazole-(K) N-3} zinc(II) was determined by single crystal X-ray diffraction.Öğe Synthesis of 1-substituted benzimidazole metal complexes and structural characterization of dichlorobis(1-phenyl-1H-benzimidazole-?N3)cobalt(II) and dichlorobis (1-phenyl-1H-benzimidazole-?N3)zinc(II)(Taylor & Francis Ltd, 2011) Sireci, Nihat; Yilmaz, Ulku; Kucukbay, Hasan; Akkurt, Mehmet; Baktir, Zeliha; Turktekin, Sevim; Buyukgungor, OrhanThe Co(II), Zn(II), Ni(II), Cu(II), and Fe(II) complexes of 1-phenylbenzimidazole were synthesized and characterized by NMR and elemental analyses. The crystal structures of dichlorobis(1-phenyl-1H-benzimidazole-kappa N-3) cobalt(II) and dichlorobis(1-phenyl-1H-benzimidazole-kappa N-3)zinc(II) have been determined by single-crystal X-ray diffraction.Öğe Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc) 2 , and base in a Suzuki-Miyaura reaction(Turkish Journal of Chemistry, 2013) Yılmaz, Ülkü; Kucukbay, Hasan; Turktekın, Sevim Celıkesır; Akkurt, Mehmet; Buyukgungor, OrhanÖz (İngilizce): Novel benzimidazolium salts having N-benzyl or N-(4-substitutedbenzyl) groups were synthesized and their microwave-promoted catalytic activity for the Suzuki Miyaura cross-coupling reaction were determined using in situ formed palladium(0) nanoparticles (PdNPs) from a catalytic system consisting of Pd(OAc) 2 /K2CO 3 in DMF/H 2 O. PdNPs were characterized by X-ray diffraction (XRD) pattern and particle size of in situ generated PdNPs from the Pd(111) plane was determined to be of diameter 19.6 nm by the Debye Scherrer equation. Moreover, the yield of the Suzuki Miyaura reactions with aryl iodides and aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (1 5) were identified by 1 H and 13 C NMR and IR spectroscopic methods, and micro analysis. The molecular structure of 5 was also determined by X-ray crystallography.Öğe Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc)2, and base in a Suzuki-Miyaura reaction(Tubitak Scientific & Technological Research Council Turkey, 2013) Yilmaz, Ulku; Kucukbay, Hasan; Turktekin Celikesir, Sevim; Akkurt, Mehmet; Buyukgungor, OrhanNovel benzimidazolium salts having N-benzyl or N-(4-substitutedbenzyl) groups were synthesized and their microwave-promoted catalytic activity for the Suzuki-Miyaura cross-coupling reaction were determined using in situ formed palladium(0) nanoparticles (PdNPs) from a catalytic system consisting of Pd(OAc)(2)/K2CO3 in DMF/H2O. PdNPs were characterized by X-ray diffraction (XRD) pattern and particle size of in situ generated PdNPs from the Pd(111) plane was determined to be of diameter 19.6 nm by the Debye-Scherrer equation. Moreover, the yield of the Suzuki-Miyaura reactions with aryl iodides and aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (1-5) were identified by H-1 and C-13 NMR and IR spectroscopic methods, and micro analysis. The molecular structure of 5 was also determined by X-ray crystallography.Öğe Synthesis of novel rhodium-xylyl linked N-heterocyclic carbene complexes as hydrosilylation catalysts(Wiley, 2008) Ozdemir, Ismail; Demir, Serpil; Sahin, Onur; Buyukgungor, Orhan; Cetinkaya, BekirReaction of ortho-xylylbis(N-2,4,6-trimethylbenzylimidazolinium);xylylbis(N-butylimidazolinium) and para-xylylbis(N-2,4,6-trimethylbenzylimidazolinium); xylylbis(N-butylimidazolinium) salts with KOBut and [RhCl(COD)](2) yields ortho- and para-xylylbis{(N-alkylimidazolidin-2-ylidene)chloro(eta(4)-1,5-cyclooctadiene) rho dium(I)} complexes (2a-d). All compounds synthesized were characterized by elemental analysis and NMR spectroscopy, and the molecular structures of the 2a and 2d were determined by X-ray crystallography. Triethylsilane reacts with acetophenone derivatives in the presence of catalytic amount of the new rhodium(I)-carbene complexes (2a-d), to give the corresponding silylethers in good yields (83-99%). Copyright (C) 2008 John Wiley & Sons, Ltd.Öğe Synthesis of palladium complexes derived from imidazolidin-2-ylidene ligands and used for catalytic amination reactions(Wiley, 2016) Karaca, Emine Ozge; Gurbuz, Nevin; Sahin, Onur; Buyukgungor, Orhan; Ozdemir, IsmailN-Aryl amination and the Buchwald-Hartwig reaction are of great synthetic and industrial interest and scientists accept their usefulness and versatility for obtaining arylamines. In this study Ag-N-heterocyclic carbene complexes were used as trans-metallation reagents for the synthesis of Pd-N-heterocyclic carbene complexes. The new Pd-N-heterocyclic carbene complexes were characterized using elemental analysis and H-1 NMR, C-13 NMR and infrared spectroscopies. The crystal structure of one, namely dichlorobis[1,3-bis(2-methylbenzyl)imidazolidin-2-yliden]palladium(II), is presented. The activity of the Pd(II) complexes in the coupling reaction of anilines or amines with bromobenzene was investigated. These complexes exhibited high catalytic activities in the direct synthesis of triarylamines and secondary amines in a single step. Copyright (C) 2016 John Wiley & Sons, Ltd.
