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Öğe Application of N,N-bis(diphenylphosphino) aniline palladium(II) complexes as pre-catalysts in Heck coupling reactions(Wiley, 2007) Gümgüm, Bahattin; Biricik, Nermin; Durap, Feyyaz; Özdemir, İsmail; Guerbuez, Nevin; Ang, Wee Han; Dyson, Paul J.; 0000-0003-0899-1948Palladium(II) complexes with N,N-bis(diphenylphosphino)aniline ligands catalyse the Heck reaction between styrene and aryl bromides, affording stilbenes in good yield. The structures of two of the complexes used as pre-catalysts have been determined by single-crystal X-ray diffraction. Copyright (c) 2007 John Wiley & Sons, Ltd.Öğe Katalizör olarak kullanılabilecek heteropoli asit tuzlarının hazırlanması(1993) Yurdakoç, M. Kadir; Güzel, Fuat; Tez, Zeki; Gümgüm, Bahattin; Akba, OsmanHPA'lann heterojen ve homojen katalizör olarak kullanılmaları çeşitli organik bileşiklerin sentezlenmesi açısından yeni bir çığır açmıştır. 1982 yılında HPA'nın katalizörlüğünde metakrolein'den metakrilik asit eldesinin endüstriyel ölçekte gerçekleştirilmesiyle başlayan bu tür uygulamalar, başta Japonya ve Rusya olmak üzere gelişmiş ülkelerde bu konudaki araştırmaları hızlandırmıştır. Bu proje çalışmasında, hazırlanan çeşitli türde heteropoli asit ve tuzlarının TGA incelemeleri yoluyla formülasyon doğrulama ve yapısal kararlılık belirlemeleri yapılmış; BET-tek nokta N2 gazı adsorpsiyonu yoluyla özgül yüzey alanları belirlenmiş; SEM fotoğrafları yoluyla amorf ya da kristal durumları görüntülenmeye çalışılmış; uygun indikatör çözeltileri yanında n-bütil amin titrasyonu yöntemiyle bu katıların asitlik şiddetleri belirlenmiş ve XRD, EDX ve FTIR incelemelerinden de elde edilen katılardaki karakteristik elementlerin ağırlık otanları ve safsızlık durumları belirlenmeye çalışılmıştır. Bu çalışmanın uzantısında ise dehidratasyon, dehidrojehasyon ve oksidasyon reaksiyonlarına birer örnek teşkil edecek şekilde uygun heterojen ve homojen model test reaksiyonları eşliğinde, elde edilen HPA ve tuzlarının katalitik özellikleri ve reaksiyon kinetiksel parametreleri belirlenmeye çalışılacaktır.Öğe A modular design of metal catalysts for the transfer hydrogenation of aromatic ketones(Wiley, 2012) Aydemir, Murat; Baysal, Akın; Gümgüm, Bahattin; 0000-0001-7294-6792The ability of transition metal catalysts to add or remove hydrogen from organic substrates by transfer hydrogenation is a valuable synthetic tool. Towards a series of novel metal complexes with a P-NH ligand, [Ph2PNHCH2C4H3O] derived from furfurylamine were synthesized. Reaction of [Ph2PNHCH2C4H3O] 1 with [Ru(6-p-cymene)(mu-Cl)Cl]2, [Ru(6-benzene)(mu-Cl)Cl]2, [Rh(mu-Cl)(cod)]2 and [Ir(5-C5Me5)(mu-Cl)Cl]2 gave a range of new monodentate complexes [Ru(Ph2PNHCH2C4H3O)(6-p-cymene)Cl2] 2, [Ru(Ph2PNHCH2C4H3O)(6-benzene)Cl2] 3, [Rh(Ph2PNHCH2-C4H3O)(cod)Cl] 4, and [Ir(Ph2PNHCH2-C4H30)(5-C5Me5)Cl2] 5, respectively. All new complexes were fully characterized by analytical and spectroscopic methods. 31P-{1H} NMR, distortionless enhancement by polarization transfer (DEPT) or 1H-13C heteronuclear correlation (HETCOR) experiments were used to confirm the spectral assignments. Following activation by KOH, compounds 25 catalyzed the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of iso-PrOH as the hydrogen source. Notably [Ru(Ph2PNHCH2-C4H3O)(6-benzene)Cl2] 3 acts as an excellent catalyst, giving the corresponding alcohols in 9899% yield in 20min at 82 degrees C (time of flight=297h-1) for the transfer hydrogenation reaction in comparison to analogous rhodium or iridium complexes. Copyright (C) 2012 John Wiley & Sons, Ltd.Öğe New bis(diphenylphosphino)aniline derivatives: Synthesis and spectroscopic characterization(Wiley-Hindawi, 2007) Biricik, Nermin; Durap, Feyyaz; Kayan, Cezmi; Gümgüm, Bahattin; 0000-0003-0899-1948; 0000-0001-5700-8546Six new multidentate bis(diphenylphosphino)amine [R-N(PPh2)(2)] ligands have been prepared from the reaction of aniline derivatives, R-NH2, with Ph2PCl in the presence of triethylamine. All of the compounds were obtained in good yields and were characterized by NMR, IR, and microanalysis. (c) 2007 Wiley Periodicals, Inc.Öğe New chiral phosphinite ligands with C2-symmetric axis and their possible applications in Ru-catalyzed asymmetric transfer hydrogenation(Wiley, 2010) Aydemir, Murat; Meriç, Nermin; Baysal, Akın; Kayan, Cezmi; Toğrul, Mahmut; Gümgüm, Bahattin; 0000-0001-7294-6792; 0000-0001-5700-8546The new chiral ligands N,N'-bis-[(1R)-1-ethyl-2-O-(diphenylphosphinite)ethyl]ethanediamide, 1, and N,N'-bis-[(1S)-1-isobutyl-2-O-(diphenylphosphinite)ethyl]ethanediamide, 2, and the corresponding ruthenium complexes 3 and 4 were prepared and their structures were elucidated by a combination of multinuclear NMR spectroscopy, IR spectroscopy and elemental analysis. Following activation by NaOH, these chiral ruthenium complexes serve as catalyst precursors for the asymmetric transfer hydrogenation of acetophenone derivatives in iPrOH. The complexes 3 and 4 showed high catalytic activity but low selectivity in asymmetric transfer hydrogenation reactions. Copyright (C) 2009 John Wiley & Sons, Ltd.Öğe P-N bond cleavage during the insertion of carbon fragments into PIII-N bonds in bis(diphenylphosphino) amines(Wiley-V C H Verlag Gmbh, 2014) Biricik, Nermin; Kayan, Cezmi; Gümgüm, Bahattin; 0000-0001-5700-8546The reaction of tertiary amine functionalized phosphines with aromatic and aliphatic aldehydes gives insertion of carbon fragments into the P-III-N bonds or P-III-N bond cleavage. The reaction of bis(diphenylphosphino) amines, la lc, with two equiv. of aldehydes in toluene afforded the P-III-N bond inserted products, 2a-4a, 4b-6b, and 3c-5c, in moderate-to-good yield. The products were characterized by IR, H-1- and P-31-NMR spectroscopy and elemental analysis.Öğe Preparation and solvent extraction of nickel complex of O, O'-dinonyldithiophosphate and its application to spectrophotometric determination of nickel in sediment samples(Wiley-V C H Verlag Gmbh, 2006) Gümgüm, Bahattin; Biricik, Nermin; Baysal, Akın; Akba, Osman; Öztürk, Gülşen; 0000-0001-7294-6792Nickel complex of O, O'-dinonyldithiophosphoric acid was prepared and characterised. Solvent extraction of nickel dinonyldithiophosphate[Ni(DNDTP)(2)] from acidic aqueous solutions into different organic phases was investigated and concentration of nickel was determined spectrophotometrically. A simple and selective spectrophotometric method was developed and applied to sediment samples.Öğe Synthesis and characterization of new (N-diphenylphosphino)-isopropylanilines and their complexes: crystal structure of (Ph2P=S)NH-C6H4-4-CH(CH3)2 and catalytic activity of palladium(II) complexes in the Heck and Suzuki cross-coupling reactions(Wiley, 2010) Aydemir, Murat; Baysal, Akın; Gürbüz, Nevin; Özdemir, İsmail; Gümgüm, Bahattin; Özkar, Saim; Çaylak, Nagihan; 0000-0001-7294-6792; 0000-0003-3201-3597; 0000-0001-6325-0216Three new (N-diphenylphosphino)-isopropylanilines, having isopropyl substituent at the carbon 2- (1) 4- (2) or 2,6- (3) were prepared from the aminolysis of chlorodiphenylphosphine with 2-isopropylaniline,4-isopropylaniline or 2,6-diisopropylaniline, respectively, under anaerobic conditions. Oxidation of 1,2 and 3 with aqueous hydrogen peroxide, elemental sulfur or gray selenium gave the corresponding oxides, sulfides and selenides (Ph2P=E)NH-C6H4-2-CH(CH3)(2), (Ph2P=E)NH-C6H4-4-CH(CH3)(2) and (Ph2P=E)NH-C6H4-2,6-[CH(CH3)(2)](2), where E = O, S, or Se, respectively. The reaction of [M(cod)Cl-2] (M = Pd, Pt; cod = 1,5-cyclooctadiene) with two equivalents of 1,2 or 3 yields the corresponding monodendate complexes [M((Ph2P)NH-C6H4-2-CH(CH3)(2))(2)Cl-2], M = Pd 1d, M = Pt 1e, [M((Ph2P)NH-C6H4-4-CH(CH3)(2))(2)Cl-2], M = Pd 2d, M = Pt 2e and [M((Ph2P)NH-C6H4-2,6-(CH(CH3)(2))(2))(2)Cl-2], M = Pd 3d, M = Pt 3e, respectively. All the compounds were isolated as analytically pure substances and characterized by NMR, IR spectroscopy and elemental analysis. Furthermore, representative solid-state structure of [(Ph2P=S)NH-C6H4-4-CH(CH3)(2)] (2b) was determined using single crystal X-ray diffraction technique. The complexes 1d-3d were tested and found to be highly active catalysts in the Suzuki coupling and Heck reaction, affording biphenyls and stilbenes, respectively. Copyright (C) 2009 John Wiley & Sons, Ltd.Öğe Synthesis and characterization of transition metal complexes of thiophene-2-methylamine: X-ray crystal structure of palladium (II) and platinum (II) complexes and use of palladium(II) complexes as pre-catalyst in Heck and Suzuki cross-coupling reactions(Wiley, 2009) Aydemir, Murat; Baysal, Akın; Durap, Feyyaz; Gümgüm, Bahattin; Özkar, Saim; Yıldırım, Leyla Tatar; 0000-0001-7294-6792; 0000-0003-0899-1948The reactions of thiophene-2-(N-diphenylphosphino)methylamine, Ph2PNHCH2-C4H3S, 1 and thiophene-2-[N,N-bis(diphenylphosphino)methylamine], (Ph2P)(2)NCH2-C4H3S, 2, with MCl2(cod) (M = Pd, Pt; cod = 1,5-cyclooctadiene) or [Cu(CH3CN)(4)]PF6 yields the new complexes [M(Ph2PNHCH2-C4H3S)(2)Cl-2], M = Pd 1a, Pt 1 b, [Cu(Ph2PNHCH2-C4H3S)(4)]PF6, 1c, and [M(Ph2P)(2)NCH2-C4H3S)Cl-2], M = Pd 2a, Pt 2b, (Cu[(Ph2P)(2)NCH2-C4H3S](2))PF6, 2c, respectively. The new compounds were isolated as analytically pure crystalline solids and characterized by (31)p-, C-13-, H-1-NMR and IR spectroscopy and elemental analysis. Furthermore, the solid-state molecular structures of representative palladium and platinum complexes of bis(phosphine)amine, 2a and 2b, respectively, were determined using single crystal X-ray diffraction analysis. The palladium complexes were tested as potential catalysts in the Heck and Suzuki cross-coupling reactions. Copyright (C) 2009 John Wiley & Sons, Ltd.Öğe Synthesis and characterizations of N,N′-bis(diphenylphosphino)-2-(aminomethyl)aniline derivatives: application of a palladium(II) complex as pre-catalyst in Heck and Suzuki cross-coupling reactions(Wiley, 2009) Aydemir, Murat; Baysal, Akın; Öztürk, Gülşen; Gümgüm, Bahattin; 0000-0001-7294-6792The reaction of 2-(aminomethyl)aniline with 2 equivalents of PPh2Cl in the presence of Et3N, proceeds in CH2Cl2 to give N,N'-bis(diphenyl phosphino)-2-(aminomethyl)ani line 1 in good yield. Oxidation of 1 with aqueous H2O2, elemental sulfur or gray selenium gave the corresponding oxide, sulfide and selenide dichalcogenides [Ph2P(E)NHC6H4CH2NHP(E)Ph-2] (E: O, 2a; S, 2b; Se, 2c), respectively. The reaction of [Ph2PNHC6H4CH2NHPPh2] with PdCl2(cod), PtCl2(cod) and [Cu(MeCN)(4)]PF6 gave the corresponding chelate complexes, PdCl(2)1, PtCl(2)1 and [Cu(1)(2)]PF6. The new compounds were fully characterized by NMR, IR spectroscopy and elemental analysis. The catalytic activity of the Pd(II) complex was tested in the Suzuki coupling and Heck reactions. The Pd(II) complex catalyzes the Suzuki coupling and Heck reaction, affording biphenyls and stilbenes respectively, in good yields. Copyright (c) 2008 John Wiley & Sons, Ltd.Öğe Synthesis of new boron complexes: application to transfer hydrogenation of acetophenone derivatives(Wiley-Blackwell, 2011) Kılıç, Ahmet; Kayan, Cezmi; Aydemir, Murat; Durap, Feyyaz; Durgun, Mustafa; Baysal, Akın; Taş, Eşref; Gümgüm, Bahattin; 0000-0001-7294-6792; 0000-0003-0899-1948; 0000-0003-3012-7582; 0000-0001-9073-4339; 0000-0001-5700-8546Two new boron complexes were synthesized from N-[3-(methylmercapto)aniline]-3,5-di-tert-butylsalicylaldimine (LH) with boron reagent BPh3 or BF3 center dot Et2O. These boron complexes are stable and easily soluble in protic solvents such as ethanol (C2H5OH) but hardly soluble in nonprotic solvents such as chloroform (CHCl3), dichloromethane (CH2Cl2) and tetrahydrofuran (THF). All new boron complexes have been fully characterized by both analytical and spectroscopic methods. The catalytic activities of complexes [LBPh2], 2, and [LBF2], 3, in the transfer hydrogenation of acetophenone derivatives were tested. Stable boron complexes were found to be efficient catalysts in the transfer hydrogenation of aromatic ketones in good conversions up to 99% in the presence of iso-PrOH/KOH. Copyright (C) 2011 John Wiley & Sons, Ltd.Öğe Synthesis of new thiol-derivatized aminophosphines and their catalytic activities in C{C coupling reactions(2015) Meriç, Nermin; Gümgüm, Bahattin; Biricik, Nermin; Azizoğlu, Sevil Şeker; Özgen, Zeynep; Kayan, CezmiA series of new aminophosphines [Ph 2 PHN-C 6 H 4 -R, where R = o -SH ( 4a ), m -SH ( 4b) or p -SH ( 4c )] were readily synthesized from cheap starting materials by the phosphorylation reaction of o , m , and p -aminothiophenols with Ph 2 PCl in the presence of triethyl amine. The new compounds were characterized by NMR and IR spectroscopy and microanalysis. In addition, aminophosphine ligands{palladium systems were investigated as precatalysts in C{C coupling reactions. Compounds 4b and 4c were proved to be excellent catalysts for Suzuki and Heck cross-coupling reactions.Öğe Synthesis, Characterization, Crystal and Molecular Structure of 1,5-Dihydro-2H-cyclopenta[1,2-b:5,4-b′]dipyridin-2-imine(Wiley-V C H Verlag Gmbh, 2007) Baysal, Akın; Durap, Feyyaz; Gümgüm, Bahattin; Yıldırım, Leyla T.; Ülkü, Dinçer; Boğa, Ayşe Dilek; Özkar, Saim; 0000-0001-7294-6792; 0000-0003-0899-1948The reaction of 1,5-diliydro-2H-cyclopenta[1,2-b:5,4-b'ldipyridin-2-one (3) with an alkylamine (butvlamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5-dihydro-2H-cyclopentafl,2-b:5.4-b']dipyridin-2-imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single-crystal X-ray-diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 2(1/c)). with two molecules in the asymmetric unit. held together by intermolecular H-bonds. Compound 4 could be interesting as a bi- or even tridentate ligand, and exhibits a strong fluorescence upon excitation at 310 nm. A mechanism, based on the observed C-N bond cleavage, is proposed.Öğe Synthesis, spectroscopic and electrochemical investigations of two vic-dioximes and their mononuclear Ni(II), Cu(II) and Co(II) metal complexes containing morpholine group(Wiley-V C H Verlag Gmbh, 2006) Kılıç, Ahmet; Taş, Eşref; Gümgüm, Bahattin; Yımaz, İsmail; 0000-0001-9073-4339; 0000-0002-5046-7456Two vic-dioxime ligands (LxH2) containing morpholine group have been synthesized from 4-[2-(dimethylaminoethyl)] morpholine with anti-phenylchloroglyoxime or anti-monochloroglyoxime in absolute THF at -15 degrees C. Reaction of two vic-dioxime ligands with MCl2 center dot nH(2)O (M: Ni, Cu or Co and n=2 or 6) salts in 1 : 2 molar ratio afforded metal complexes of type [M(LxH)(2)] or [M(LxH)(2)center dot 2H(2)O]. All of metal complexes are non-electrolytes as shown by their molar conductivities (Lambda(m)) in DMF (dimethyl formamide) at 10(-3) mol.L-1. Structures of the ligands and metal complexes have been solved by elemental analyses, FT-IR, UV-Vis, H-1 NMR and C-13 NMR, magnetic susceptibility measurements, molar conductivity measurements. Furthermore, redox properties of the metal complexes were investigated by cyclic voltammetry.Öğe Teknik alüminyumoksit yardımıyla atık sulardan fosfat giderilmesi ve geri kazanılması(1996) Tez, Zeki; Gümgüm, BahattinBurada verilen sürecin adsorpsiyon basamağında su, aktif alümina ile temasa getirilir ve aktif alümina, $OH^-$ iyonlarının değişimi yoluyla fosfatla yüklenir. Rejenerasyon için yüklü aktif alümina seyrettik sodyum hidroksit çözeltisiyle işlenir ve bu sırada $OH^-$ iyonlarıyla iyon değişimine giren fosfat, çözeltiye geçer. Fosfatı değerlendirilebilir bir biçim haline getirmek için rejenerasyon çözeltisine katı kalsiyum oksit eklenir. Bu sırada kalsiyum fosfat ve kalsiyum hidroksit çökeleği oluşur. Sodyum hidroksit çözeltisi çökelekten süzüldükten sonra yeniden rejenerasyonda kullanılır. Süreçte kimyasal madde olarak yalnızca Ca(0H)2 tüketilir. Suya hiçbir yabancı iyon verilmez ve hem aktif alümina hem de NaOH çevrime geri verilir. Yaklaşık 10 mg P/1 lik bir giriş derişiminde adsorpsiyon fazının başlangıcındaki çıkış derişimi yaklaşık 0,3 mg P/1 dir.Öğe Three new vic-dioxime ligands: Synthesis, characterization, spectroscopy, and redox properties of their mononuc ear nickel(II) complexes(John Wiley & Sons Inc, 2007) Kılıç, Ahmet; Taş, Eşref; Gümgüm, Bahattin; Yılmaz, İsmail; 0000-0001-9073-4339; 0000-0001-9410-2945; 0000-0002-5046-7456Nickel(II) complexes with three new vic-dioxime reagents, N-(ethyl-4-amino-l-piperidine carboxylate)phenylglyoxime (L2H2), N-(ethyl-4-amino- 1-piperidine carboxylate)glyoxime (L2H2) and N,N'-bis(ethyl-4-amino-1-piperidine carboxylate)glyoxime (L3H2), have been prepared. Mononuclear nickel(II) complexes with a metal/ligand ratio of 1:2 were prepared using Ni(II) salt. All these nickel(II) complexes are nonelectrolytes as shown by their molar conductivities (Lambda(M)) in DMF solution at 10(-3) M concentration. The ligands are soluble in common solvents such as DMSO, DMF, CHCl3, and C2H5OH. The ligands and their Ni(II) complexes were characterized by elemental analyses, FT-IR, UV-visible, H-1 NMR, 13 C NMR, magnetic susceptibility measurements, cyclic voltammetry, and molar conductivities (Am). The cyclic voltammetric measurements show that [Ni(L1H)(2)] and [Ni(L2H)(2)]complexes exhibit almost similar electrochemical behavior, with two reduction and two oxidation processes based on either metals or oxime moities, while [Ni(L3H)(2)center dot 2H(2)O] complex displays irreversible, with one reduction and one oxidation processes based on oxime moity. This main difference could be attributed to the highly polarized [Ni(L3H)(2)center dot 2H(2)O] complex that has four carboxylate groups attached to piperidine on the oxime moieties. (c) 2007 Wiley Periodicals, Inc.
