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Öğe Aminophosphine ligands: synthesis, coordination chemistry, and activity of their palladium(II) complexes in Heck and Suzuki cross-coupling reactions(Springer, 2011) Kayan, Cezmi; Biricik, Nermin; Aydemir, MuratThe reaction of 4-aminodiphenylamine or 2-aminofluorene with two equivalents of PPh2Cl in the presence of Et3N gives new bis(diphenylphosphino) amines N,N-bis(diphenylphosphino)-4-aminodiphenylamine 1 and N, N-bis(diphenylphosphino)-2-aminofluorene 2 in good yields. Oxidation of 1 or 2 with hydrogen peroxide, elemental sulfur or gray selenium affords the corresponding chalcogen derivatives. The palladium and platinum complexes of these P-N-P donor ligands were prepared by the reaction of the bis(phosphino) amines with MCl2(cod) (M = Pd or Pt, cod = cycloocta-1,5-diene). All the new compounds have been characterized by analytical and spectroscopic methods, including H-1-P-31 NMR, H-1-C-13 HETCOR, or H-1-H-1 COSY correlation experiments. The Pd(II) complexes were investigated as catalysts in the Suzuki and Heck reactions; both showed good catalytic activity affording high yields of the desired products.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 Comparison of microwave and conventional digestion of copper ores and determination of heavy metals by ICP-AES(Asian Journal Of Chemistry, 2006) Akba, Osman; Ozturk, Gulsen; Biricik, Nermin; Gumgum, BahattinThis paper summarizes the results obtained in applying conventional and microwave digestion techniques to Maden and Hazro copper materials for subsequent analysis by inductively coupled plasma (ICP-AES).Öğe Dialkil ditiyofosforik asitler ile metal-dinonil ditiyofosforların sentezi ve analitik uygulamalarının araştırılması(2018) Biricik, Nermin; Gümgüm, BahattinÖzet Klasik yöntemle dinonil ditiyofosforik asidin ve ilk kez tarafımızdan olmak üze re mikrodalga yöntemiyle dinonil, dioktil, diheptil, dihekzil, dipentil ve dibütil ditiyofos forik asidin hazırlanma koşullan incelendi. Klasik yöntemle dinonil ditiyofosforik asit için, 72-74 °C ve 10 saat sürenin yeterli olduğu görüldü. Dibütil ve dipentil ditiyofos forik asit için 1 dakika süreyle 504 W, dihekzil, diheptil, dioktil ve dinonil ditiyofosforik asit için ise, 3 dakika süreyle 504 W güç uygulanmasının asitlik yüzdesi bakımından en iyi sonucu verdiği belirlendi. Her iki yöntemle elde edilen asitlerin metal kompleksleri karşılaştırıldığında, UV / görünür alan spektrumlan ve ekstraksiyon davranışları açısından fark göstermedikleri saptandı. Cu(II), Zn(E), Pb(II), Ni(II), Cd(II) ve Co(II) metallerinin ekstraksiyonunda mikrodalga yöntemiyle hazırlanan asitler kullanıldı. Bu asitlerin zincir uzunluğuna bağlı olarak ekstraksiyon davranışlarında herhangi bir farklılık gözlenmedi. Çeşitli çözücüler ile tuzların ve pH'nın ekstraksiyon üzerine önemli bir etki oluşturmadığı, ancak ekstraktant konsantrasyonunun bu konuda önemli olduğu belirlendi. Dinonil ditiyofosforik asidin Cu(II), Cu(I), Pb(H), Ni(E), Co(H), Cd(II) ve Hg(H) metal kompleksleri sentezlenerek, TGA, UV ve İR özellikleri incelendiğinde, bu bileşiklerin IR'leri arasında anlamlı bir farkın olmadığı görüldü. Cu(II), Pb(II), Ni(H), Co(II) ve Hg(H) iyonları, metal dinonil ditiyofosfat bileşiklerine dönüştürülerek spekt- rofotometrik olarak tayin edildi.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 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 Spectroscopic and Thermogravimetric Investigation of Cd(II) Dinonyldithiophosphate: Removal of Cadmium from Aqueous Solutions(Hindawi Ltd, 2015) Biricik, Nermin; Gumgum, Hadice Budak; Gumgum, BahattinDinonyldithiophosphoric acid (HDDTP) was synthesised from the reaction of phosphorus pentasulphide and nonyl alcohol. Dinonyldithiophosphate complex of cadmium [Cd(DDTP)(2)] was prepared by mixing solutions of Cd(II) with HDDTP in ethanol at room temperature. The acid and its complex were characterised by elemental analysis and spectroscopy. The thermal behaviour of Cd(DNDTP)(2) was investigated by thermogravimetric analysis. Removal of Cd(II) from aqueous media by HDDTP solution was also studied. The optimum conditions for removal of Cd(II) were investigated for effects of solvent, pH, contact time, concentration, and inorganic anions. Cd(II) was quantitatively removed from aqueous solutions at the pH range of 0.5 < pH < 6, under the conditions that the stoichiometric ratio of HDDTP/Cd(II) = 2/1. It can be stated that contact of the Cd(II) with HDDTP was sufficient for quantitative removing of cadmium from acidic aqueous solutions.Öğe Synthesis and characterization of 4,4?,-diaminodiphenylmethane Schiff bases(Asian Journal Of Chemistry, 2007) Biricik, Nermin; Kayan, CezmiFive novel Schiff bases were prepared from the reaction of 4,4'-diaminodiphenylmethane with acetylacetone; 3-chloroacetylacetone, salicylaldehyde, benzaldehyde and m-tolualdehyde. The synthesized Schiff-bases were characterized by spectroscopic methods and elemental analysis.Öğe Synthesis and characterization of ether-derivatized aminophosphines and their application in C-C coupling reactions(Elsevier Science Sa, 2010) Biricik, Nermin; Kayan, Cezmi; Gumgum, Bahattin; Fei, Zhaofu; Scopelliti, Rosario; Dyson, Paul J.; Gurbuz, NevinFour new bis(phosphino) amine ligands (Ph2P)(2)N-C6H3-R, where R = 3,5-OMe (1), 2,5-OMe (2), 2,4-OMe (3) or 3,4-OMe (4), were prepared via aminolysis of the corresponding dimethoxyanilines with 2 equiv. of diphenylphosphine chloride in the presence of triethyl amine. Oxidation of these ligands with aqueous H2O2, elemental S-8 or Se powder afforded the corresponding chalcogen oxides 1a-4a, sulfides 1b-4b and selenides 1c-4c in good yields. Reaction of 1-4 with [MCl2(cod)] (M = Pt, Pd; cod = cycloocta-1,5-diene) in equimolar ratios afforded cis-[MCl2{(Ph2P)(2)N-C6H3-R}] (M = Pt; R = 3,5-OMe 1d, R = 2,5-OMe 2d, R = 2,4-OMe 3d, and R = 3,4-OMe 4d. M = Pd; R = 3,5-OMe 1e, R = 2,5-OMe 2e, R = 2,4-OMe 3e, and R = 3,4-OMe 4e). Similarly, reaction of [Cu(CH3CN)(4)]PF6 with the 1-4 in 1:2 ratio gave [Cu{(Ph2P)(2)N-C6H3-R}(2)]PF6 (R = 3,5-OMe 1f, 2,5-OMe 2f, 2,4-OMe 3f and 3,4-OMe 4f). All new compounds were fully characterized by spectroscopy and elemental analysis and the molecular structures of seven representative compounds were determined by single-crystal X-ray crystallography. In addition, the palladium complexes were investigated as pre-catalysts in C-C coupling reactions. (C) 2009 Elsevier B.V. All rights reserved.Öğe Synthesis and characterizations of N,N-bis(diphenylphosphino)ethylaniline derivatives and X-ray crystal structure of palladium (II), platinum (II) complexes(Pergamon-Elsevier Science Ltd, 2008) Durap, Feyyaz; Biricik, Nermin; Guemguem, Bahattin; Oezkar, Saim; Ang, Wee Han; Fei, Zhaofu; Scopelliti, RosarioN,N-Bis(diphenylphosphino)ethylaniline compounds, [Ph2P](2)N-C6H4-C2H5, with ethyl groups at the ortho- and para-positions have been synthesized. Oxidation of the aminophosphines with hydrogen peroxide, elemental sulfur and selenium gave the corresponding oxides, sulfides and selenides [Ph2P(E)](2)N-C6H4-C2H5 (E = O, S, Se). Complexes [MCl2{(Ph2P)(2)N-C6H4-(C2H5)}] (M = Pd, Pt) and [Cu{(Ph2P)(2)N-C6H4-C2H5)(2)]PF6 were obtained by the reaction of NN-bis(diphenylphosphino)ethylaniline with [MCl2(COD)] (M = Pd, Pt) and (Cu(MeCN)(4)]PF6. The new compounds were characterized by NMR, IR spectroscopy and microanalysis. In addition, representative solid-state structures of the palladium and platinum complexes were determined using single crystal X-ray diffraction analyses. (C) 2007 Elsevier Ltd. All rights reserved.Öğe Synthesis and reactivity of bis(diphenylphosphino)amine ligands and their application in Suzuki cross-coupling reactions(Elsevier Science Sa, 2012) Kayan, Cezmi; Biricik, Nermin; Aydemir, Murat; Scopelliti, RosarioTwo new bis(diphenylphosphino) amines, N,N-bis(diphenylphosphino) benzidine 1 and N, N-bis(diphenylphosphino)- 3,3-dimethoxybenzidine 2 were prepared by aminolysis. Their corresponding oxides, sulfides and selenides were readily prepared by reaction with hydrogen peroxide, elemental sulfur or grey selenium, respectively. Symmetric dinuclear palladium and platinum complexes were also isolated from the reaction with [M(cod)Cl-2] (M = Pd or Pt, cod = cycloocta-1,5-diene). All compounds were characterized by IR and NMR spectroscopy and elemental analysis and the structure of [(Ph2P)(2)N-C6H4-C6H4-N(PPh2)(2)] was determined by single crystal X-ray diffraction. The catalytic activity of palladium complexes in Suzuki coupling reactions was also investigated. (C) 2012 Elsevier B.V. All rights reserved.Öğe Synthesis and reactivity of N,N-bis(diphenylphosphino)dimethylaniline compounds(Springer, 2007) Biricik, Nermin; Durap, Feyyaz; Gumgum, Bahattin; Fei, Zhaofu; Scopelliti, RosarioNew chalcogenides and complexes of N,N-bis(diphenylphosphino)dimethylanilines were prepared by the reaction of N,N-bis(diphenylphosphino)dimethylaniline ligands with aqueous H2O2, elemental S and Se and transition metal complexes based on Cu, Pd and Pt. All the new compounds have been characterised by spectroscopy and the molecular structures of the three complexes of N,N-bis(diphenylphosphino)dimethylanilines have been determined by X-ray crystallography.Öğe Synthesis of new aminophosphine complexes and their catalytic activities in C-C coupling reactions(Elsevier Science Sa, 2008) Biricik, Nermin; Durap, Feyyaz; Kayan, Cezmi; Guemguema, Bahattin; Guerbuez, Nevin; Oezdemir, Ismail; Ang, Wee HanTwo new aminophosphines, benzyl-N(Ph2P)(2) and 2-picolyl-N(Ph2P)(2), have been synthesized. Oxidation of the aminophosphines with either hydrogen peroxide, elemental sulfur and selenium gave the corresponding oxides, sulfides and selenides benzyl-N(Ph2P=E)(2) and 2-picolyl-N(Ph2P=E)(2), where E = O, S, or Se. Complexes [benzyl-N(Ph2P)(2)]MCl2 and [2-picolyl-N(Ph2P)(2)]MCl2, where M = Pd, Pt, were obtained by the reaction of the aminophosphines with MCl2(cod). The new compounds were characterised by NMR, IR spectroscopy and microanalysis. Furthermore, representative solid-state structures of the palladium and platinum complexes were determined using single crystal X-ray diffraction analysis. The palladium complexes were further investigated as potential catalysts in C-C coupling reactions. (c) 2008 Elsevier B. V. All rights reserved.Öğe Synthesis of new thiol-derivatized aminophosphines and their catalytic activities in C-C coupling reactions(Tubitak Scientific & Technological Research Council Turkey, 2015) Biricik, Nermin; Meric, Nermin; Kayan, Cezmi; Ozgen, Zeynep; Azizoglu, Sevil Seker; Gumgum, BahattinA series of new aminophosphines [Ph2PHN-C6H4-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 Ph2PCl 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 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 Thermal and spectral characterization of Co(II) and Cu(II) dinonyldithiophosphates: Removal of Co(II) and Cu(II) from Aqueous Solutions(Chemical Publishing Co., 2015) Gümgüm, Hadice Budak; Biricik, NerminDinonyldithiophosphoric acid (HDDTP) was prepared by addition of phosphorus pentasulphide to nonyl alcohol. Dinonyldithiophosphate complexes of Co(II) and Cu(II) with general formula [M(DDTP)2] [M = Co(II) or Cu(II)] were prepared by mixing solutions of M(II) with dinonyldithiophosphoric acid in ethanol at room temperature. The acid and its complexes were caharacterized by elemental analysis and infrared, ultraviolet-visible and inductively coupled plasma-optical emission spectrometry. The thermal behaviour of M(DNDTP)2 was investigated by thermogravimetric analysis under a nitrogen atmosphere. Removal of Co(II) and Cu(II) from aqueous media by dinonyldithiophosphoric acid solutions were investigated. The optimum conditions for extraction, such as the organic solvent, pH of the aqueous phase, time of equilibration, concentration and effect of anions, were studied. It was found that dinonyldithiophosphoric acid is an effective substance for removing Cu(II) and Co(II) from aqueous solutions.
