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Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması

Year 2008, Volume: 12 Issue: 1, 1 - 8, 09.04.2009

Abstract

Bu çalışma 5,11,17,23-tetra-ter-bütil-25,27-bis(3siyano)propoksikaliks[4]aren (2) ve bunun birden fazla kaliksaren birimininin bir arada olduğu uygun polimerik yapısının sentezini ve ekstraksiyon özelliklerini içermektedir. Başlangıç maddesi olarak kullanılan p-ter-bütilkaliks[4]aren literatürdeki metotlara göre sentezlendi. Daha sonra bu bileşiğe literatürdeki metotlar uyarlanarak 2 nolu bileşik elde edildi. Polimerik yapı (3) bileşik 2 ile Merrifield reçinesinin reaksiyonuyla elde edildi. Son olarak bu bileşiklerin faz-transfer çalışmaları sıvı-sıvı ekstraksiyon metodu kullanılarak gerçekleştirildi. Ekstraksiyon sonuçlarından görülmektedir ki monomer 2 Hg+2 katyonuna karşı bir seçicilik göstermektedir. Halbuki, bunun polimeri (3) Ni2+ hariç seçilen metallerin hepsini iyi bir şekilde organik faza taşımaktadır.

References

  • Agrawal, Y.K., Sharma, K.R. 2005. Speciation, Liquid-Liquid Extraction, Sequential Separation, Preconcentration, Transport and ICP-AES Determination of Cr(III), Mo(VI) and W(VI) with Calix-crown Hydroxamic acid in High Purity Grade Materials and Environmental Samples. Talanta, 67, 112-120.
  • Alpoguz, H.K., Memon, S., Ersoz, M., Yılmaz, M. 2004. Transport Kinetics of Hg2+ Through Bulk Liquid Membrane Using Calix[4]arene Ketone Derivative as Carrier, Sep. Sci. Technol., 39, 799-810.
  • Arnaud-Neu, F., Collins, E.M., Deasy, M., Ferguson, G., Haris, S.J. Kaitner, B., Lough, A.J., McKervey, M.A., Marques, E., Ruhl, B.L., Schwing-Weill, M.J. Stewart, E.M. 1989. Synthesis, X-Ray Crystal Structures, and Cation-Binding Properties of Alkyl Calixaryl Esters and Ketones, A New Family of Macrocyclic Molecular Receptors. J. Am. Chem. Soc., 111, 8681-8691.
  • Barakat, N., Burgard, M., Asfari, Z., Vicens, J., Montavon, G., Duplâtre, G. 1998. Solvent extraction of alkaline- earth ions by dicarboxylated calix[4]arenes. Polyhedron, 17, 3649-3656.
  • Bozkurt, S., Karakucuk, A., Sirit, A., Yılmaz, M. 2005. Synthesis of Two Calix[4]arene Diamide Derivatives for Extraction of Chromium (VI). Tetrahedron, 61, 10443-10448.
  • Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M-J., Egberink, R.J.M., Jong, F., Reinhoudt, D.N. 1995. Synthesis, Complexation, and Membrane Transport Studies of 1, 3-alternate Calix[4]arene-crown-6 Conformers, New Class of Cesium Selective Ionophores. J. Am. Chem. Soc., 117, 2767.
  • Deligöz, H., Yılmaz, M. 1995. Liquid- Liquid Extraction of Transition Metal Cation by Calixarenes- based Cyclic Ligands. Solvent Extr. Ion. Exch., 13, 19-26.
  • Demirel, A., Dogan, A., Akkus, G., Yılmaz, M., Kılıc, E. 2006. Silver(I)-selective PVC Membrane Potentiometric Sensor Based on a Recently Synthesized Calix[4]arene. Electroanalysis, 18, 1019-1027.
  • Gungor, O., Memon, S., Yılmaz, M., Roundhill, D.M. 2005. Synthesis of Alkyl Nitrile and Alkyl Benzonitrile Derivatives of Calix[4]arene and Their Polymer Supported Analogues: A Comparative Study in Two-Phase Extraction Systems. React. Funct. Polym., 63, 1-9.
  • Gutsche, C. D., Iqbal, M. 1986. Calixarenes. 18. Synthesis Procedures for p-tert - Butycalix[4]arene. J. Org. Chem., 51, 742-745.
  • Gutsche, C.D., Iqbal, M. 1990. p-tert-Butylcalix[4] arene. Org. Syn., 68, 234-235.
  • Kaledkowski, A., Trochimczuk, A.W. 2006. Novel Chelating Resins Containing Calix [4] pyrroles: Synthesis and Sorptive Properties. React. and Funct. Polym., 66, 740-746.
  • Kaledkowski, A., Trochimczuk, A.W. 2006. Chelating Resin Containing Hybrid Calixpyrroles: New Sorbent for Noble Metal Cations. React. and Funct. Polym., 66, 957-966.
  • Karakucuk, A., Kocabas, E., Sirit, A., Memon, S., Yılmaz, M., Roundhill, D. M. 2005. Polymer Supported Calix [4] arene Schiff Bases: A Novel Chelating Resin for Hg2+ and Dichromate Anions. J. Macromol. Sci. Part A: Pure Appl. Chem., 42, 691-704.
  • Marcus, Y., Kertes, A.S. 1969. Ion Exchange and Solvent Extraction of Metal Complexes. Wiley-Interscience, London, 1046 pp.
  • Marinsky, J.A., Marcus, Y. 1992. Ion-exchange and Solvent Extraction. Marcel Dekker, New York, 378 pp.
  • Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D., Yılmaz, M. 2003. Polymer Supported Calix[4]arene Derivatives for the Extraction of Metals and Dichromate Anions. J. Polym. Environ., 11, 67–74.
  • Memon, S., Oğuz O., Yılmaz, A., Tabakcı, M., Yılmaz, M., Ertul, Ş. 2001. Synthesis and Extraction Study of Calix[4]arene Dinitrile Derivatives Incorporated in a Polymeric Backbone with Bisphenol-A. Polymers and the Environment, 9, 97-101.
  • Memon, S., Tabakci., Roundhill, D.M., Yılmaz, M. 2006. Synthesis and Evaluation of the Cr (VI) Extraction Ability of Amino/nitrile Calix[4]arenes Immobilized onto a Polymer Backbone. Reactive and Functional Polymers, 66, 1342-1349.
  • Memon, S, Uysal, G., Yılmaz, M. 2000. Selective Complexation of Hg2+ by Biscalix[4]arene Nitriles. Separation Sci. and Tech., 35,1247-1256.
  • Memon, S., Yılmaz, A., Roundhill, D. M., Yılmaz, M. 2004. Synthesis of Polymeric Calix[4]arene Dinitrile and Diamino-Derivatives: Exploration of Their Extraction Properties Towards Dichromate Anion. J. Macromol. Sci. Part A: Pure Appl. Chem., 41, 435–449.
  • Memon, S., and Yılmaz, M. 2001. A Complimentary Study of Calixarene Based by Functional Receptor for Alkali or Transition Metal Cations and Cr2O7 = . J. Molecular. Struct., 595, 1, 101-109.
  • Mendes, A. R., Gregório, C.C., Barata, P.D., Costa, A.I., Prata, J.V. 2005. Linear and Crosslinked Copolymers of p-tert-butylcalix[4]arene Derivatives and Styrene: New Synthetic Approaches to Polymer-bound Calix[4]arenes. React., and Funct. Polym., 65, 9-21.
  • Mohapatra, P.K., Ansara, S.A., Sarkar, A., Bhattacharyya, A., Manchanda, V.K. 2006. Evaluation of Calix-crown Ionophores for Selective Separation of Radio-cesium from Acidic Nuclear Waste Solution. Analytica Chimica Acta, 571, 308-314.
  • Ohto, K., Fujimoto, Y., Inoue, K. 1999. Stepwise Extraction of Two Lead Ions with a Single Molecule of Calix[4]arene Tetracarboxylic Acid. Analytics Chimica Acta, 387, 61-6.
  • Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R. 2005. New Azothiacalix[4]arenes Containing Biheterocyclic Subunits: Extraction and Complexation Properties. Supramol. Chem., 17, 227-232.
  • Pearson, R.G. 1963. Hard and soft acids and bases. J. Am. Chem. Soc., 85, 3533-3534.
  • Pedersen, C.J. 1967. Cyclic Polyethers and Their Complexes with Metal Salts. J. Am. Chem. Soc., 89, 7017-7036.
  • Shinkai, S., Shigematsu, K., Michiko, S., Manabe, O. 1982. Photoreponsive Crown Ethers. Part 6. Ion Transport Mediated by Photoinduced Cis Trans Interconversion of Azobis (Benzocrown Ethers). J. Chem. Soc. Perkin Trans. I, 2735-2738.
  • Tabakci, M., Ersöz, M, Yılmaz, M. 2006. A Calix[4]arene-containing Polysiloxane Resin for Removal of Heavy Metals and Dichromate Anion. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 43, 1–13.
  • Tabakci, M., Memon, S., Yılmaz, M. 2007. Synthesis and Extraction Properties of New ‘Proton - Switchable’ Tri-and Tetra-substituted Calix[4]arene Derivatives Bearing Pyridinium Units. Tetrahedron, 63, 6861 6865.
  • Talanov, V.S., Roper, E.D., Buie, N.M., Talanova, G.G. 2007. A New Fluorogenic Mono-ionizable Calix[4]arene Dansylcarboxamide as a Selective Chemosensor of Soft Metal Ions, Tl+ and Hg2+. Tetrahedron Letters, 48, 8022–8025.
  • Tilki, T., Şener, İ.¸ Karcı, F., Gülce, A., Deligöz, H. 2005. An Approach to The Synthesis of Chemically Modified Bisazocalix[4]arenes and their Extraction Properties. Tetrahedron, 61, 9624–9629.
  • Tu, C., Surowiec, K., Bartsch, R.A. 2007. Efficient Divalent Metal Cation Extractions with Di-ionizable Calix[4]arene-1, 2-crown-4 Compounds. Tetrahedron, 63, 4184-4189.
  • Uysal, G., Memon, S., Yılmaz, M. 2002. Synthesis and Binding Properties of Polymeric Calix[4]arene Nitriles. Reactive and Funct. Polym., 50, 77-84.
  • Uysal Akkus, G., Memon, S., Gürkas, D.E., Aslan, S., Yılmaz, M. 2008. The Synthesis and Metal Cation Extraction Studies of Novel Polymer-bound Calix(aza)crowns. React. Funct. Polym. 68, 125-132.
  • Vicens, J., Bohmer, V. 1991. Calixarenes: A Versatile Class of Macrocyclic Compounds Topics in Inclusion Science. Kluwer Academic Publishers, Dordrecht. 263 pp.
  • Weiss, H., Bertine, K., Kolse, M., Goldberg, F.D. 1975. The Chemical Composition of Greenland Glaciers. Geochim, Cosmochim, Acta, 39, 1-10.
  • Yılmaz, A., Memon, S., Yılmaz, M. 2002. Synthesis and Study of Allosteric Effects on Extraction Behaviour of Novel Calixarene-based Dichromate Anion Receptors. Tetrahedron, 58, 7735-7740.
  • Yılmaz, A., Yılmaz, M., Bartsch, R.A. 2006. Synthesis of a Calix[4]crown-6 Cone Conformer-based Oligomer and its Metal Cation Extraction Abilities. J. Macromol. Sci. Part A: Pure and Appl. Chem., 43, 637–645.
  • Yılmaz, M. 1998. Synthesis and Characterisation of Complexes of Copper(II), Nickel(II) and Cobalt (II) with A Schiff Base Derivative of p-tert Butylcalix[4]arene. Synthesis of React. Inorg. Met-Org. Chem., 28, 1759-1768.
  • Yılmaz, M., Deligöz, H. 1996. Selective Extraction of Fe3+ Cation by Calixarene Based Cyclic Ligands. Separation Science and Technology, 31, 2395-2402.
  • Yordanov, A.T., Roundhill, D.M. 1996. Chemically Modified Calix[4]arenes as Selective Complexants for Hevy Metal Ions, Comparison with Crowns and Thiacrowns and Oxyion Salts. New J. Chem., 20, 447-451.
  • Zhou, X., Li, X., Zeng, Z. 2006. Solid-phase Microextraction Coupled with Capillary Electrophoresis for the Determination of Propranolol Enantiomers in Urine Using a Sol-gel Derived Calix[4]arene Fiber. Journal of Chromatography A, 1104, 359-365.
Year 2008, Volume: 12 Issue: 1, 1 - 8, 09.04.2009

Abstract

References

  • Agrawal, Y.K., Sharma, K.R. 2005. Speciation, Liquid-Liquid Extraction, Sequential Separation, Preconcentration, Transport and ICP-AES Determination of Cr(III), Mo(VI) and W(VI) with Calix-crown Hydroxamic acid in High Purity Grade Materials and Environmental Samples. Talanta, 67, 112-120.
  • Alpoguz, H.K., Memon, S., Ersoz, M., Yılmaz, M. 2004. Transport Kinetics of Hg2+ Through Bulk Liquid Membrane Using Calix[4]arene Ketone Derivative as Carrier, Sep. Sci. Technol., 39, 799-810.
  • Arnaud-Neu, F., Collins, E.M., Deasy, M., Ferguson, G., Haris, S.J. Kaitner, B., Lough, A.J., McKervey, M.A., Marques, E., Ruhl, B.L., Schwing-Weill, M.J. Stewart, E.M. 1989. Synthesis, X-Ray Crystal Structures, and Cation-Binding Properties of Alkyl Calixaryl Esters and Ketones, A New Family of Macrocyclic Molecular Receptors. J. Am. Chem. Soc., 111, 8681-8691.
  • Barakat, N., Burgard, M., Asfari, Z., Vicens, J., Montavon, G., Duplâtre, G. 1998. Solvent extraction of alkaline- earth ions by dicarboxylated calix[4]arenes. Polyhedron, 17, 3649-3656.
  • Bozkurt, S., Karakucuk, A., Sirit, A., Yılmaz, M. 2005. Synthesis of Two Calix[4]arene Diamide Derivatives for Extraction of Chromium (VI). Tetrahedron, 61, 10443-10448.
  • Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud, F., Fanni, S., Schwing, M-J., Egberink, R.J.M., Jong, F., Reinhoudt, D.N. 1995. Synthesis, Complexation, and Membrane Transport Studies of 1, 3-alternate Calix[4]arene-crown-6 Conformers, New Class of Cesium Selective Ionophores. J. Am. Chem. Soc., 117, 2767.
  • Deligöz, H., Yılmaz, M. 1995. Liquid- Liquid Extraction of Transition Metal Cation by Calixarenes- based Cyclic Ligands. Solvent Extr. Ion. Exch., 13, 19-26.
  • Demirel, A., Dogan, A., Akkus, G., Yılmaz, M., Kılıc, E. 2006. Silver(I)-selective PVC Membrane Potentiometric Sensor Based on a Recently Synthesized Calix[4]arene. Electroanalysis, 18, 1019-1027.
  • Gungor, O., Memon, S., Yılmaz, M., Roundhill, D.M. 2005. Synthesis of Alkyl Nitrile and Alkyl Benzonitrile Derivatives of Calix[4]arene and Their Polymer Supported Analogues: A Comparative Study in Two-Phase Extraction Systems. React. Funct. Polym., 63, 1-9.
  • Gutsche, C. D., Iqbal, M. 1986. Calixarenes. 18. Synthesis Procedures for p-tert - Butycalix[4]arene. J. Org. Chem., 51, 742-745.
  • Gutsche, C.D., Iqbal, M. 1990. p-tert-Butylcalix[4] arene. Org. Syn., 68, 234-235.
  • Kaledkowski, A., Trochimczuk, A.W. 2006. Novel Chelating Resins Containing Calix [4] pyrroles: Synthesis and Sorptive Properties. React. and Funct. Polym., 66, 740-746.
  • Kaledkowski, A., Trochimczuk, A.W. 2006. Chelating Resin Containing Hybrid Calixpyrroles: New Sorbent for Noble Metal Cations. React. and Funct. Polym., 66, 957-966.
  • Karakucuk, A., Kocabas, E., Sirit, A., Memon, S., Yılmaz, M., Roundhill, D. M. 2005. Polymer Supported Calix [4] arene Schiff Bases: A Novel Chelating Resin for Hg2+ and Dichromate Anions. J. Macromol. Sci. Part A: Pure Appl. Chem., 42, 691-704.
  • Marcus, Y., Kertes, A.S. 1969. Ion Exchange and Solvent Extraction of Metal Complexes. Wiley-Interscience, London, 1046 pp.
  • Marinsky, J.A., Marcus, Y. 1992. Ion-exchange and Solvent Extraction. Marcel Dekker, New York, 378 pp.
  • Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D., Yılmaz, M. 2003. Polymer Supported Calix[4]arene Derivatives for the Extraction of Metals and Dichromate Anions. J. Polym. Environ., 11, 67–74.
  • Memon, S., Oğuz O., Yılmaz, A., Tabakcı, M., Yılmaz, M., Ertul, Ş. 2001. Synthesis and Extraction Study of Calix[4]arene Dinitrile Derivatives Incorporated in a Polymeric Backbone with Bisphenol-A. Polymers and the Environment, 9, 97-101.
  • Memon, S., Tabakci., Roundhill, D.M., Yılmaz, M. 2006. Synthesis and Evaluation of the Cr (VI) Extraction Ability of Amino/nitrile Calix[4]arenes Immobilized onto a Polymer Backbone. Reactive and Functional Polymers, 66, 1342-1349.
  • Memon, S, Uysal, G., Yılmaz, M. 2000. Selective Complexation of Hg2+ by Biscalix[4]arene Nitriles. Separation Sci. and Tech., 35,1247-1256.
  • Memon, S., Yılmaz, A., Roundhill, D. M., Yılmaz, M. 2004. Synthesis of Polymeric Calix[4]arene Dinitrile and Diamino-Derivatives: Exploration of Their Extraction Properties Towards Dichromate Anion. J. Macromol. Sci. Part A: Pure Appl. Chem., 41, 435–449.
  • Memon, S., and Yılmaz, M. 2001. A Complimentary Study of Calixarene Based by Functional Receptor for Alkali or Transition Metal Cations and Cr2O7 = . J. Molecular. Struct., 595, 1, 101-109.
  • Mendes, A. R., Gregório, C.C., Barata, P.D., Costa, A.I., Prata, J.V. 2005. Linear and Crosslinked Copolymers of p-tert-butylcalix[4]arene Derivatives and Styrene: New Synthetic Approaches to Polymer-bound Calix[4]arenes. React., and Funct. Polym., 65, 9-21.
  • Mohapatra, P.K., Ansara, S.A., Sarkar, A., Bhattacharyya, A., Manchanda, V.K. 2006. Evaluation of Calix-crown Ionophores for Selective Separation of Radio-cesium from Acidic Nuclear Waste Solution. Analytica Chimica Acta, 571, 308-314.
  • Ohto, K., Fujimoto, Y., Inoue, K. 1999. Stepwise Extraction of Two Lead Ions with a Single Molecule of Calix[4]arene Tetracarboxylic Acid. Analytics Chimica Acta, 387, 61-6.
  • Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R. 2005. New Azothiacalix[4]arenes Containing Biheterocyclic Subunits: Extraction and Complexation Properties. Supramol. Chem., 17, 227-232.
  • Pearson, R.G. 1963. Hard and soft acids and bases. J. Am. Chem. Soc., 85, 3533-3534.
  • Pedersen, C.J. 1967. Cyclic Polyethers and Their Complexes with Metal Salts. J. Am. Chem. Soc., 89, 7017-7036.
  • Shinkai, S., Shigematsu, K., Michiko, S., Manabe, O. 1982. Photoreponsive Crown Ethers. Part 6. Ion Transport Mediated by Photoinduced Cis Trans Interconversion of Azobis (Benzocrown Ethers). J. Chem. Soc. Perkin Trans. I, 2735-2738.
  • Tabakci, M., Ersöz, M, Yılmaz, M. 2006. A Calix[4]arene-containing Polysiloxane Resin for Removal of Heavy Metals and Dichromate Anion. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 43, 1–13.
  • Tabakci, M., Memon, S., Yılmaz, M. 2007. Synthesis and Extraction Properties of New ‘Proton - Switchable’ Tri-and Tetra-substituted Calix[4]arene Derivatives Bearing Pyridinium Units. Tetrahedron, 63, 6861 6865.
  • Talanov, V.S., Roper, E.D., Buie, N.M., Talanova, G.G. 2007. A New Fluorogenic Mono-ionizable Calix[4]arene Dansylcarboxamide as a Selective Chemosensor of Soft Metal Ions, Tl+ and Hg2+. Tetrahedron Letters, 48, 8022–8025.
  • Tilki, T., Şener, İ.¸ Karcı, F., Gülce, A., Deligöz, H. 2005. An Approach to The Synthesis of Chemically Modified Bisazocalix[4]arenes and their Extraction Properties. Tetrahedron, 61, 9624–9629.
  • Tu, C., Surowiec, K., Bartsch, R.A. 2007. Efficient Divalent Metal Cation Extractions with Di-ionizable Calix[4]arene-1, 2-crown-4 Compounds. Tetrahedron, 63, 4184-4189.
  • Uysal, G., Memon, S., Yılmaz, M. 2002. Synthesis and Binding Properties of Polymeric Calix[4]arene Nitriles. Reactive and Funct. Polym., 50, 77-84.
  • Uysal Akkus, G., Memon, S., Gürkas, D.E., Aslan, S., Yılmaz, M. 2008. The Synthesis and Metal Cation Extraction Studies of Novel Polymer-bound Calix(aza)crowns. React. Funct. Polym. 68, 125-132.
  • Vicens, J., Bohmer, V. 1991. Calixarenes: A Versatile Class of Macrocyclic Compounds Topics in Inclusion Science. Kluwer Academic Publishers, Dordrecht. 263 pp.
  • Weiss, H., Bertine, K., Kolse, M., Goldberg, F.D. 1975. The Chemical Composition of Greenland Glaciers. Geochim, Cosmochim, Acta, 39, 1-10.
  • Yılmaz, A., Memon, S., Yılmaz, M. 2002. Synthesis and Study of Allosteric Effects on Extraction Behaviour of Novel Calixarene-based Dichromate Anion Receptors. Tetrahedron, 58, 7735-7740.
  • Yılmaz, A., Yılmaz, M., Bartsch, R.A. 2006. Synthesis of a Calix[4]crown-6 Cone Conformer-based Oligomer and its Metal Cation Extraction Abilities. J. Macromol. Sci. Part A: Pure and Appl. Chem., 43, 637–645.
  • Yılmaz, M. 1998. Synthesis and Characterisation of Complexes of Copper(II), Nickel(II) and Cobalt (II) with A Schiff Base Derivative of p-tert Butylcalix[4]arene. Synthesis of React. Inorg. Met-Org. Chem., 28, 1759-1768.
  • Yılmaz, M., Deligöz, H. 1996. Selective Extraction of Fe3+ Cation by Calixarene Based Cyclic Ligands. Separation Science and Technology, 31, 2395-2402.
  • Yordanov, A.T., Roundhill, D.M. 1996. Chemically Modified Calix[4]arenes as Selective Complexants for Hevy Metal Ions, Comparison with Crowns and Thiacrowns and Oxyion Salts. New J. Chem., 20, 447-451.
  • Zhou, X., Li, X., Zeng, Z. 2006. Solid-phase Microextraction Coupled with Capillary Electrophoresis for the Determination of Propranolol Enantiomers in Urine Using a Sol-gel Derived Calix[4]arene Fiber. Journal of Chromatography A, 1104, 359-365.
There are 44 citations in total.

Details

Primary Language English
Journal Section TEMEL BİLİMLER
Authors

Gülderen Uysal Akkuş This is me

Dilek Erol This is me

Publication Date April 9, 2009
Published in Issue Year 2008 Volume: 12 Issue: 1

Cite

APA Uysal Akkuş, G., & Erol, D. (2009). Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 12(1), 1-8. https://doi.org/10.19113/sdufbed.51068
AMA Uysal Akkuş G, Erol D. Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması. J. Nat. Appl. Sci. April 2009;12(1):1-8. doi:10.19113/sdufbed.51068
Chicago Uysal Akkuş, Gülderen, and Dilek Erol. “Nitril Grubu Tasıyan Kaliks[4]aren Ve Polimer Destekli Türevinin Sentezi Ve Civa Taşıma Özelliklerinin Karşılaştırılması”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 12, no. 1 (April 2009): 1-8. https://doi.org/10.19113/sdufbed.51068.
EndNote Uysal Akkuş G, Erol D (April 1, 2009) Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 12 1 1–8.
IEEE G. Uysal Akkuş and D. Erol, “Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması”, J. Nat. Appl. Sci., vol. 12, no. 1, pp. 1–8, 2009, doi: 10.19113/sdufbed.51068.
ISNAD Uysal Akkuş, Gülderen - Erol, Dilek. “Nitril Grubu Tasıyan Kaliks[4]aren Ve Polimer Destekli Türevinin Sentezi Ve Civa Taşıma Özelliklerinin Karşılaştırılması”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 12/1 (April 2009), 1-8. https://doi.org/10.19113/sdufbed.51068.
JAMA Uysal Akkuş G, Erol D. Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması. J. Nat. Appl. Sci. 2009;12:1–8.
MLA Uysal Akkuş, Gülderen and Dilek Erol. “Nitril Grubu Tasıyan Kaliks[4]aren Ve Polimer Destekli Türevinin Sentezi Ve Civa Taşıma Özelliklerinin Karşılaştırılması”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 12, no. 1, 2009, pp. 1-8, doi:10.19113/sdufbed.51068.
Vancouver Uysal Akkuş G, Erol D. Nitril Grubu Tasıyan Kaliks[4]aren ve Polimer Destekli Türevinin Sentezi ve Civa Taşıma Özelliklerinin Karşılaştırılması. J. Nat. Appl. Sci. 2009;12(1):1-8.

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