1,4-PİRAZİN-2,3-DİKARBOKSİLİK ASİTİN YENİ PROTON TRANSFER TUZU İLE GEÇİŞ METAL KOMPLEKSLERİNİN SENTEZİ VE KARAKTERİZASYONU

Bu çalışmada 1,4-pirazin-2,3-dikarboksilik asit (H2pyzdc) ve 2-(piperazin-1-il)etanol (H2Etppz) bileşiklerinin tepkimesinden proton transfer tuzu (H2Etppz)(pyzdc)(1) sentezlendi. Proton transfer tuzunun (1) yapısı; elementel analiz, 1H ve 13C NMR, FTIR ve UV-Vis yöntemlerinden yararlanılarak aydınlatıldı. Proton transfer tuzunun (1) Mn(II) (2), Co(II) (3), Cu(II) (4) ve Zn(II) (5) kompleksleri elde edildi. Komplekslerin yapıları; FTIR, UV-Vis, ICP-OES ve manyetik duyarlılık yöntemleri sonuçlarına göre önerildi.

SYNTHESIS AND CHARACTERIZATION OF TRANSITION METAL COMPLEXES OF NEW PROTON TRANSFER SALT OF 1,4-PYRAZINE-2,3-DICARBOXYLIC ACID

In this study, the proton tansfer salt (H2Etppz)(pyzdc)(1) was synthesized from the reaction of 1,4-pyrazine-2,3-dicarboxylic acid (H2pyzdc) with 2-(piperazine-1-yl)ethanol (H2Etppz). The proton transfer salt (1) was characterized using elemental analysis, 1H and 13C NMR, FTIR, UV-Vis techniques. The Mn(II) (2), Co(II) (3), Cu(II) (4) and Zn(II) (5) complexes of proton transfer salt (1) were synthesized. The structures of the complexes; have been suggested according to results of the FTIR, UV-Vis, ICP-OES and magnetic susceptibility methods

___

  • [1] Mirzaei, M Aghabozorg, H., Eshtiagh-Hosseini, H., (2011), Determination of the salt tolerance of some barley genotypes and the characteristics affecting tolerance. Journal of Iranian Chemical Society, 8, 580-607.
  • [2] Ockwig, N.W., Delgado-Friedrichs, O., O’Keeffe, M., Yaghi, O.M., (2005), Reticular Chemistry: Occurrence and Taxonomy of Nets and Grammar for the Design of Frameworks, Accounts of Chemical Research, 38, 176-182.
  • [3] Spokoyny, A.M., Kim, D., Sumrein, A., Mirkin, C.A., (2009), Infinite coordination polymer nano- and microparticle structures, Chemical Society Reviews, 38, 1218-1227.
  • [4] Lampeka, Ya.D., Tsymbal, L.V., (2004), Framework materials based on azamacrocyclic complexes of transition metals and carboxylates, Theoretical and Experimental Chemistry, 40, 345-371.
  • [5] Yesilel, O.Z., Mutlu, A., Buyukgungor, O.,(2008), A new coordination mode of pyrazine-2,3-dicarboxylic acid and its first monodentate complexes: Syntheses, spectral, thermal and structural characterization of [Cu(pzdca)(H2O)(en)2] · H2O and [Cu(pzdca)(H2O)(dmpen)2], Polyhedron, 2471-2477.
  • [6] Mirzaei, M., Eshtiagh-Hosseini, H., Alfi, N., Aghabozorg, H., Attar Gharamaleki, J., Beyramabadi, S.A., Khavasi, H.R., Salimi, A.R., Shokrollahi, A., Aghaei, R., Karami, E., (2011), Syntheses, crystal, molecular structures, and solution studies of Cu(II), Co(II), and Zn(II) coordination compounds containing pyridine-2,6-dicarboxylic acid and 1,4-pyrazine-2,3-dicarboxylic acid: comparative computational studies of Cu(II) and Zn(II) complexes, Structural Chemistry, 22, 1365-1377.
  • [7] Eshtiagh-Hosseini, H., Aghabozorg, H., Mirzaei, M., (2010), catena-Poly[diacridinium [zinc(II)-di--pyrazine-2,3-dicarboxylato-3N1,O2:O3;O3:N1,O2]]. Acta Crystallographica, Section E66, m882.
  • [8] Eshtiagh-Hosseini, H., Aghabozorg, H.,Shamsipur, M., Mirzaei, M., Ghanbari, M., (2011), Hydrothermal synthesis, X-Ray crystallography, TGA and SEM analyses and solution studies of a novel Nano-sized 1D zinc(II) coordination Polymer. Journal of Iranian Chemical Society, 8, 762-774.
  • [9] Mirzaei, M., Eshtiagh-Hosseini, H., Hassanpoor, A., Barba, V., (2012), X-Ray structure of a 1D-coordination polymer of copper(II) bearing pyrazine-2,3-dicarboxylic acid and 2-aminopyrimidine, Journal of Serbian Chemistry Society, 77, 67-73.
  • [10] Eshtiagh-Hosseini, H., Hassanpoor, A., Alfi, N., Mirzaei, M., Fromm, K.M., Shokrollahi, A., Gschwind, F., Karami, E., (2010), Synthesis, X-ray crystal structure, thermal and solution studies of a centrosymmetric metal–organic polymer based on proton transfer methodology, Journal of Coordination Chemistry, 63, 3175-3186.
  • [11] Yeşilel, O. Z., Mutlu, A., Büyükgüngör, O., (2008), A new coordination mode of pyrazine-2,3-dicarboxylic acid and its first monodentate complexes: Syntheses, spectral, thermal and structural characterization of [Cu(pzdca)(H2O)(en)2] · H2O and [Cu(pzdca)(H2O)(dmpen)2], Polyhedron, 27(11), 2471-2477.
  • [12] Okubo, T., Kondo, M., Kitagawa, S., (1997), Synthesis, structure, and magnetic properties of one-dimensional copper(II) coordination polymer, [Cu(pyrazine-2,3-dicarboxylate)(H2O)2]·2H2On, Synthetic Metals, 85, 1661-1662.
  • [13] Ptasiewicz-Bąk, H., Leciejewicz, J., (1999), Crystal and molecular structures of nickel(II) complexes with azine-2,3-dicarboxylic and 3-aminopyrazine-2-carboxylic acids, Polish Journal of Chemistry, 73, 717-725.
  • [14] Tang,Q., Zhang, C-J., Zhang, C-H., Wang, H-Y., Chen, Y-G., Liu, S-X., (2012), Two sandwich-type compounds from Keggin polyoxometalate, d10 metals and the product of in situ catalyzed decarboxylation of pyrazine-2,3- dicarboxylic acid, Inorganic Chemistry, Communications, 15, 238-242.
  • [15] Gryz, M., Starosta, W., Leciejewicz, J., (2007), Doubly bridged molecular ribbons in the structure of an ionic complex, hydronium zinc(II) pyrazine-2,3-dicarboxylate, Journal of Coordination Chemistry, 58, (11), 931-935.
  • [16] Günay, G., Yeşilel, O. Z., Soylu, M. S., Keskin, S., Dal, H., (2011), Two novel 2D and 3D coordination polymers constructed from pyrazine-2,3-dicarboxylic acid and chloride bridged secondary building units, Synthetic Metals, 161(21-22), 2471-2480.
  • [17] Mirzaei, M.,Eshtiagh-Hosseini, H., Hassanpoor, A., Szymańska-Buzar, T., Mague, J.T., Korabik, M., Kochel, A., (2012), Two new CuII 1D-coordination polymers containing 1,4-pyrazine-2,3-dicarboxylic acid, 2-aminopyridine, and 5-bromo-6-methyl-2-(4-methylpiperazine-1-yl)pyrimidine-4-amine: X-ray crystal structure, spectroscopic and magnetic studies, Inorganica Chimica Acta, 391, 232-238.
  • [18] Fazil, S., Ravindran, R., Devi, A.S. and Bijili, B.K., (2012), Structural studies of 1- phenyl-2,3-dimethyl-5-oxo-1,2-dihydro-1H-pyrazol-4-ammonium-2[(2- carboxyphenyl)- disulfanyl]-benzoate, Journal of Molecular Structure, 1021, 147–152.
  • [19] Majerz, I. and Olovsson, I., (2010), Influence of proton transfer on the geometry of the donor and acceptor in NHN+ hydrogen bonds, Journal of Molecular Structure, 976, 11–18.
  • [20] Özdemir, N., (2012), Structural and spectroscopic characterization of 2-mesityl-1Hbenzo[d]imidazol-3- ium chloride: A combined experimental and theoretical analysis, Spectrochimica Acta, Part A, 91, 51-60.
  • [21] Shehab, O.R. and Mansour, A.M., (2015), Sparfloxacin charge transfer complexes with 2,3-dichloro-5,6- dicyano-1,4-benzoquinone and tetracyanoquinodimethane: Molecular structures, spectral, and DFT studies. Journal of Molecular Structure, 1093, 186-194.
  • [22] Rzokee, A.A. and Ahmad, A., (2014), Synthesis, spectroscopic studies and thermal analysis of charge- transfer complex of 2,20-bipyridine with 4-hydroxybenzoic acid in different polar solvents, Journal of Molecular Structure, 1076, 453– 460.
  • [23] Refat, M.S., Adam, A.M.A. and Saad, H.A., (2015), Utility of charge-transfer complexation for the assessment of macrocyclic polyethers: Spectroscopic, thermal and surface morphology characteristics of two highly crown ethers complexed with acido acceptors, J. Mol. Struct., 1085, 178-190.
  • [24] Gopi, R., Ramanathan, N. and Sundararajan, K., (2015), Hydrogen-bonded complexes of acetylene and acetonitrile: A matrix isolation infrared and computational study, Journal of Molecular Structure, 1083, 364–373.
  • [25] Weiss, N.M., Waller, A.W. and Phillips, J.A., (2016), Infrared spectrum of CH3CN– HCl in solid neon, and modeling matrix effects in CH3CN–HCl and H3N–HCl, Journal of Molecular Structure, 1105, 341–349.
  • [26] Perpetuo, G.J. and Janczak, J., (2016), Structural and spectroscopic characterization of 1--(diaminomethylene) thiouron-1-ium benzoate and bis(1-(diaminomethylene)- thiouron-1-ium) phthalate trihydrate, Journal of Molecular Structure, 1105, 434–443.
  • [27] Dimitrova, Y. and Daskalova, L.I., (2007), Solvent effects on vibrational spectra of hydrogen-bonded complexes of propanedinitrile (malononitrile) and dimethyl sulfoxide (DMSO): Ab initio and DFT studies, Journal of Molecular Structure Theochem, 823, 65–73.
  • [28] Al-Ahmary, K.M., Habeeb, M. and Al-Solmy, E.A., (2011), Spectroscopic studies of the hydrogen bonded charge transfer complex of 2-aminopyridine with π-acceptor chloranilic acid in different polar solvents, Journal of Moecular Liquids, 162, 129–134.
  • [29] Alexeev, Y.E., Kharisov, B.I., Hermandez, T.C. and Garnovski, A.D., (2010), Coordination motifs in modern supramolecular chemistry, Coordination Chemistry Review, 254, 794–831.
  • [30] Stepanovs, D., Jure, M. and Mishnev, A., (2015), Preparation and crystal structure of sildenafil salicylate, Mendeleev Communication, 25, 49–50.
  • [31] Vepuri, S.B., Devarajegowda, H.C. and Soliman, M.E., (2016), Synthesis, characterization and molecular modelling of a novel dipyridamole supramolecule e X-ray structure, quantum mechanics and molecular dynamics study to comprehend the hydrogen bond structure reactivity relationship, Journal of Molecular Structure, 1105, 194–204.
  • [32] Büyükkıdan, N., Yenikaya, C., İlkimen, H., Karahan, C., Darcan, C., and Şahin, E., (2013), Synthesis, characterization and antimicrobial activity of a novel proton salt and its Cu(II) complex. Russian Journal of Coordination Chemistry, 39, 96-103.
  • [33] Büyükkıdan, N., Büyükkıdan, B., Demir, N., Karahan, C., (2018), Piridin-2,6-dikarboksilik asitin proton transfer tuzu ve bunun Ni(II) ve Cu(II) komplekslerinin sentezi ve karakterizasyonu, Dpü Fen Bil. Enst. Dergisi, 41, 1-12.
  • [34] Büyükkıdan, N., Demir, N., Büyükkıdan, B., (2017), Bazı karboksilik asitlerden elde edilen proton transfer tuzlarının ve Cu (II) komplekslerinin sentezi ve karakterizasyonu, BAUN Fen Bil. Enst. Dergisi 19(2), 137-152.
  • [35] Singh, K., Siddiqui, H.H., Shakya, P., Bagga, P., Kumar, A., Khalid, M., Arif, M., Alok, S., (2015) Piperazine-A Biologically Active Scaffold. International Journal of Pharmaceutial Science and Research, 6(10), 4145-58.
  • [36] Cunica, W., Claudia, R. B., (2009). Structure of (2R,3S) - 4-(aryl methyl)-1-(4- hydroxy butyl) piperazine, potential anti malarial agents. Zeitscrift fur krystallographie, 224(9), 461-470.
  • [37] Bihan, G.L., Rondu, F., Tounian, A.P., (1999). Design and Synthesis of Imidazoline Derivatives Active on Glucose Homeostasis in a Rat Model of Type II Diabetes. 2. Syntheses and Biological Activities of 1,4-Dialkyl-, 1,4-Dibenzyl, and 1-Benzyl-4-alkyl-2-(4’5’-dihydro-1’ H imidazol-2’-yl) piperazines and Isosteric Analogues of Imidazoline. Journal of Medicinal Chemistry, 42(9), 1587-1603.
  • [38] Acri, J.B., Siedleck, B.K., Witkin, J.M., (1996). Effects of benztropine on behavioral and toxic effects of cocaine: comparison with atropine and the selective dopamine uptake inhibitor 1-[2-( diphenylmethoxy) ethyl]-4-(3-phenyl-propyl)-piperazine. Journal of Pharmacology Experimantal Therapeutics, 277(1), 198-206.
  • [39] Cecchetti, V., Schiaffella, F., (2000). 1,4-Benzothiazinyloxy alkylpiperazine derivatives as potential antihypertensive agents, Bioorganic and Medicinal Chemistry Letters, 10, 465-468.
  • [40] Yenikaya, C., Büyükkıdan, N., Sarı, M., Keşli, R., İlkimen, H., Bülbül, M., and Büyükgüngör, O., (2011), Synthesis, characterization, and biological evaluation of Cu(II) complexes with the proton transfer salt of 2,6-pyridinedicarboxylic acid and 2-amino-4-methylpyridine, Journal of Coordination Chemistry, 64,19, 3353–3365.
  • [41] Büyükkıdan, N., Yenikaya, C., İlkimen, H., Karahan, C., Darcan, C., Korkmaz, T. and Süzen, Y., (2015), Synthesis, characterization and biological activities of metal(II)dipicolinate complexes derived from pyridine-2,6-dicarboxylic acid and 2-(piperazin-1-yl)ethanol, Journal of Molecular Structure, 1101, 139-146.
  • [42] Sallomi, I.J., Shaheen, A.J., (1998), Complexes of cobalt (II), nickel (II) and copper (II) with ortho-and para-phenylenediamine derivatives, Polyhedron, 17, 1429– 1433.