Araştırma Makalesi
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Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties

Yıl 2018, Sayı: 3, 12 - 16, 31.12.2018

Öz

In this study,  a novel
(E,E)-dioxim containing a diazatetrathiadioxa macrobicyclic moieties 
(19E,
20E)-6,7,14,15,18,21,24,25-oktahydro-13,26-(ethanothioethano-thioethano)dibenzo

[14,15:8,9]-[1,4,10,13,7,16]dioxadithiadiazacyclooctadecino[2,3-g]
quinoxaline- 19,20,27,34-tetrone 19,20-dioxime (H2L) has been
synthesized by reacting cyanogen-di-N-oxide with 2,3-diamino-6,7,14,15,22,23-hexahydro-8,21-(ethanothioethanothioethano)tribenzo[b,h,n][1,4,10,





13,7,16]dioxadithiadiazacyclooctadecine-25,32-dione (8), which was prepared by the reduction
of
2,3-dinitro-6,7,14,15,22,23-hexahydro-8,21-(ethanothioethanothioethano)-tribenzo[b,h,n]
[1,4,10,13,7,16]dioxodithiadiazacyclooctadecine-25,32dione (7). The macrobicyclic (7) was synthesized by the condensation
reaction of compound (5) with
compound (6) in the presence of the
Na2CO3 under an argon atmosphere in the refluxing
acetonitrile. Mononuclear complex (11) with metal:ligand ratio 1:2 of
this ligand has been synthesized by reacting the vic-dioxime (H2L)
with NiCl2.6H2O. The new compounds were characterized by
a combination of elemental analysis, 1H- and 13C-NMR, IR
and MS spectral data.

Kaynakça

  • 1. Kukushkini, V.Y., Pombeiro, A.J.L., Oxime and Oximate Metal Complexes: Unconventional Synthesis and Reactivity, Coord. Chem. Rev. 1999, 181, 147-175.2. Smith, A.G., Tasker, P.A., White, D.J., The structures of phenolic oximes and their complexes, Coord. Chem. Rev. 2003, 241, 61-85.3. Stynes, D.V., Vernik, I.; Zobi, F., Iron complexes of borylated vicinal dioxime macrocycles, Coord. Chem. Rev. 2002, 233, 273-287.4. Bilgin. A., Ertem, B., Gök Y, Dilber, G., Kılıçarslan, M., Synthesis and characterization of a new (E,E)-dioxime and its mono and polynuclear complexes containing a 14-membered dithiadiaza macrocyclic moiety, J. Coord. Chem. 2004, 57(10), 883–891.5. Kantekin, H., Dilber, G., Gök, Y., Ocak, Ü., Abbasoğlu, R., Synthesis and Characterization of A New (E, E)-Dioxime and Its Mono and Heterotrinuclear Complexes Containing 18-Membered Dithiatetraazamacrocycle, Trans. Met. Chem. 2003, 28, 51–57.6. Özer, M., Kandaz, M., Özkaya, A.R., Bulut, M., Güney, O., Fluorescent vic dioxime type ligand and its mono and di nuclear complexes the preparation spectroscopy and electrochemistry of its various complexes, Dyes Pigments, 2008, 76,125-132.7. Kurtoğlu, M., Serin, S., Syntheses and characterization of 4-(11-chloro-3,6,9-trioxaundecyloxy) phenylamino-glyoxime and its complexes with copper(II), nickel(II), and cobalt(II), Synth. React. Inorg. Met.- Org. Chem. 2002, 32 (3), 629-637.8. Burdinskii,D., Birkelbachi,F., Werheymuller,T., Florke, U., Hampt, H.J., Lengen, M., Encapsulation by a Chromium(III)-Containing Bicyclic Ligand Cage. Synthesis, Structures, and Physical Properties of Heterometal Complexes CrIIIMCrIII [M = (H+)2, Li(I), Mg(II), Cu(II), Ni(II), Ni(IV), Co(III), Fe(II), Fe(III), Mn(II)], Inorg. Chem. 1998, 37, 1009-1020.9. Ruiz, R., Julve, M., Faus, J., Lioret, F., Munoz, M.C., Ournaux, Y., Ferromagnetic Coupling between Copper(II) Centers through the Diamagnetic Zinc(II) Ion: Crystal Structure and Magnetic Properties of [Cu(2)Zn(Hdmg)(2)(dmg)(2)(H(2)O)].-0.5H(2)dmg.H(2)O (H(2)dmg = Dimethylglyoxime), Inorg. Chem. 1997, 36, 3434-3439.10. Leonard, J.P., Novotnik, D.P., Neirinck, R.D., Technetium-99m-d, 1-HM-PAO: a new radiopharmaceutical for imaging regional brain perfusion using SPECT--a comparison with iodine-123 HIPDM., J. Nucl. Med. 1986, 27, 1819-1823.11. Dilworth, J.R., Parrott, S.J., The biomedical chemistry of technetium and rhenium, Chem. Soc.Rev. 1998, 27, 43-55.12. Hall, I.H., Bastow, K.F., Warren, A.E., Cytotoxicity of cobalt complexes of furan oximes in murine and human tissue‐cultured cell lines, Appl. Organomet. Chem. 1999, 13, 819-828.13. Lukevics, E.; Abele, R.; Fleisher, M., Fluoride ion catalyzed silylation of ketoximes by hydrosilanes, J. Mol. Catal. A. Chem. 2003,198, 89-98. 14. Sellmann, D., Utz, J., Heinemann, F.W., Transition-Metal Complexes with Sulfur Ligands. 132.(1) Electron-Rich Fe and Ru Complexes with [MN(2)S(3)] Cores Containing the New Pentadentate Ligand 'N(2)H(2)S(3)'(2)(-) (= 2,2'-Bis(2-mercaptophenylamino)diethyl Sulfide(2-)), Inorg. Chem. 1999, 38, 459-466. 15. W.D. Cheng, D.S. Wu, J. Shen, S.P. Huang, Z. Xie, H. Zhang, Y.J. Gong, From molecule to bulk material: optical properties of hydrogen-bonded dimers [C12H12N4O2AgPF6]2 and [C28H28N6O3AgPF6]2 depend on the arrangement of the oxime moieties, Chem-Eur J. 2007,13 (18), 5151-5159.16. Ohta, K., Higashi, R., Kejima, M.I., Yamamoto, I., Kobayashi, N., Disk-like liquid crystals of transition metal complexes: Critical molecular structure change from columnar to lamellarliquid crystal in bis(diphenylglyoximato)-nickel(II)-based complexes, J. Mater. Chem. 1998, 8, 1979-1991. 17. S. Kumar, R. Singh, H. Singh, Amide–ether–amine-containing macrocycles: synthesis, transport and binding metal cations, J. Chem. Soc. Perkin. Trans. 1999, 1, 3049-3054. 18. Finke, R.G., Schiraldi, D.A., Mayer, B.J., Towards the unification of coenzyme B12-dependent diol dehydratase stereochemical and model studies: The bound radical mechanism, Coord. Chem. Rev. 1984, 54,1-22. 19. Dilworth, J.R., Parrott, S.J., The biomedical chemistry of technetium and rhenium. Chem. Soc. Rev. 1998, 27, 43.20. Chakravorty, A., Structural chemistry of transition metal complexes of oximes, Coord. Chem. Rev. 1974, 13, 1-46.21. Brown, B.G., The chemistry of vitamin B12 and related inorganic model systems. Prog. Inorg. Chem. 1973, 18, 177-286. 22. Thomas, T.W.; Underhill, A.F., Metal–metal interactions in transition-metal complexes containing infinite chains of metal atoms, Chem. Soc. Rew. 1972, 1, 99-120. 23. U. Ocak, Y. Gok, H.B. Senturk, Evaluation of mononuclear Ni(II) complex of a tetra-cryptanded vic-dioxime and its model compound 14-membered N2O2S2 macrobicyclic ligand as Pb 2+, Cd 2+, and Hg 2+ extractants, Sep. Sci. Technol. 2009, 44 (5),1240-1249. 24. Gök, Y., Kantekin, H., Alp, H., Özdemir, M., Synthesis and characterization of the free ligand 5,6:13,14‐dibenzo‐9,10‐benzo(15‐crown‐5)‐2,3‐bis(hydroxyimino)-7,12‐dioxo‐1,4,8,11‐tetraazacyclotetradecane and its mono and trinuclear complexes, Z. Anorg. Allg. Chem. 1995, 621,1237-1242. 25. Durmuş, M., Ahsen,V.,Luneau, D., Pécaut, Synthesis and structures of morpholine substituted new vic-dioxime ligand and its Ni(II) complexes, J. Inorg. Chem. Acta, 2004, 357, 588-594.26. Biyiklioğlu, Z., Dilber, G., Kantekin, H., The synthesis and characterization of a new (e,e)-dioxime and its mono and heterotrinuclear complexes containing dioxadithiadiazamacrobicyclic moieties, transition metal chemistry, Trans. Met. Chem. 2006, 31, 979-985.27. Chandra, S., Kumar, R., Synthesis and spectral studies on mononuclear complexes of chromium(III) and manganese(II) with 12-membered tetradentate N2O2, N2S2 and N4 donor macrocyclic ligands, Trans. Met. Chem. 2004, 29, 269-275.28. Kantekin, H., Ocak, Ü., Gök,Y., Alp, H., Synthesis and characterization of new (E,E)-dioxime and its homo and heterotrinuclear complexes containing dioxadithiadiaza-macrobicycle moiety, Polyhedron 2002, 21, 1865-1870.29. Perrin, D.D., Armarego, W.L.F., Perin, D.R. Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, New York, 1985.30. Gök, Y., Kantekin, H., Synthesis and characterization of novel (E,E)-dioxime and its mono- and heterotrinuclear complexes, Acta Chem. Scand. 1997, 51, 664-671. 31. Pedersen, S.B., Larsen, E., Anti-amphi and cis-trans İsomerisms in some bis-(dioximato)nickel(II) complexes, Acta Chem. Scand. 1973, 27, 3291-3301.32. Nakamura, A., Konishi, A., Otsuka, S., Chiral metal complexes. Part 5. Cobalt(II) and some other transition-metal complexes of chiral vic-dioximate ligands derived from D-camphor and L-β-pinene, J. Chem. Soc. Dalton Trans. 1979, 488-495.33. Gök, Y., Bekaroğlu, Ö., The Synthesis and Complex Formatirn of Stererisomers of some new α-Dioximes, Synth. React. Inorg. Met.-Org. Chem. 1981, 11, 621-631.34. Gök, Y., Kantekin, H., synthesis and characterization of new (e,e)-dioximes and their BF2+-capped mononuclear and trinuclear complexes with Ni(II), Pd(II) and Co(III), New J. Chem. 1995, 19, 461-467.35. Szczepura, L.F., Muller, J.G., Bessel, C.A., See, R.F., Janik, T.S., Churchill, M.R., Takeuchi, K., Characterization of protonated trans bis(dioxime) ruthenium complexes: crystal structures of trans-Ru(DPGH)2(NO)Cl, trans-[Ru(DMGH)(DMGH2)(NO)Cl]Cl, and trans-Ru(DMGH)2(NO)Cl, Inorg. Chem. 1992, 31, 859-869.36. Lance, K.A.; Goldsby, K.A.; Busch, D.H., Effective new cobalt(II) dioxygen carriers derived from dimethylglyoxime by the replacement of the linking protons with difluoroboron(1+), Inorg. Chem. 1990, 29, 4537-4544.
Yıl 2018, Sayı: 3, 12 - 16, 31.12.2018

Öz

Kaynakça

  • 1. Kukushkini, V.Y., Pombeiro, A.J.L., Oxime and Oximate Metal Complexes: Unconventional Synthesis and Reactivity, Coord. Chem. Rev. 1999, 181, 147-175.2. Smith, A.G., Tasker, P.A., White, D.J., The structures of phenolic oximes and their complexes, Coord. Chem. Rev. 2003, 241, 61-85.3. Stynes, D.V., Vernik, I.; Zobi, F., Iron complexes of borylated vicinal dioxime macrocycles, Coord. Chem. Rev. 2002, 233, 273-287.4. Bilgin. A., Ertem, B., Gök Y, Dilber, G., Kılıçarslan, M., Synthesis and characterization of a new (E,E)-dioxime and its mono and polynuclear complexes containing a 14-membered dithiadiaza macrocyclic moiety, J. Coord. Chem. 2004, 57(10), 883–891.5. Kantekin, H., Dilber, G., Gök, Y., Ocak, Ü., Abbasoğlu, R., Synthesis and Characterization of A New (E, E)-Dioxime and Its Mono and Heterotrinuclear Complexes Containing 18-Membered Dithiatetraazamacrocycle, Trans. Met. Chem. 2003, 28, 51–57.6. Özer, M., Kandaz, M., Özkaya, A.R., Bulut, M., Güney, O., Fluorescent vic dioxime type ligand and its mono and di nuclear complexes the preparation spectroscopy and electrochemistry of its various complexes, Dyes Pigments, 2008, 76,125-132.7. Kurtoğlu, M., Serin, S., Syntheses and characterization of 4-(11-chloro-3,6,9-trioxaundecyloxy) phenylamino-glyoxime and its complexes with copper(II), nickel(II), and cobalt(II), Synth. React. Inorg. Met.- Org. Chem. 2002, 32 (3), 629-637.8. Burdinskii,D., Birkelbachi,F., Werheymuller,T., Florke, U., Hampt, H.J., Lengen, M., Encapsulation by a Chromium(III)-Containing Bicyclic Ligand Cage. Synthesis, Structures, and Physical Properties of Heterometal Complexes CrIIIMCrIII [M = (H+)2, Li(I), Mg(II), Cu(II), Ni(II), Ni(IV), Co(III), Fe(II), Fe(III), Mn(II)], Inorg. Chem. 1998, 37, 1009-1020.9. Ruiz, R., Julve, M., Faus, J., Lioret, F., Munoz, M.C., Ournaux, Y., Ferromagnetic Coupling between Copper(II) Centers through the Diamagnetic Zinc(II) Ion: Crystal Structure and Magnetic Properties of [Cu(2)Zn(Hdmg)(2)(dmg)(2)(H(2)O)].-0.5H(2)dmg.H(2)O (H(2)dmg = Dimethylglyoxime), Inorg. Chem. 1997, 36, 3434-3439.10. Leonard, J.P., Novotnik, D.P., Neirinck, R.D., Technetium-99m-d, 1-HM-PAO: a new radiopharmaceutical for imaging regional brain perfusion using SPECT--a comparison with iodine-123 HIPDM., J. Nucl. Med. 1986, 27, 1819-1823.11. Dilworth, J.R., Parrott, S.J., The biomedical chemistry of technetium and rhenium, Chem. Soc.Rev. 1998, 27, 43-55.12. Hall, I.H., Bastow, K.F., Warren, A.E., Cytotoxicity of cobalt complexes of furan oximes in murine and human tissue‐cultured cell lines, Appl. Organomet. Chem. 1999, 13, 819-828.13. Lukevics, E.; Abele, R.; Fleisher, M., Fluoride ion catalyzed silylation of ketoximes by hydrosilanes, J. Mol. Catal. A. Chem. 2003,198, 89-98. 14. Sellmann, D., Utz, J., Heinemann, F.W., Transition-Metal Complexes with Sulfur Ligands. 132.(1) Electron-Rich Fe and Ru Complexes with [MN(2)S(3)] Cores Containing the New Pentadentate Ligand 'N(2)H(2)S(3)'(2)(-) (= 2,2'-Bis(2-mercaptophenylamino)diethyl Sulfide(2-)), Inorg. Chem. 1999, 38, 459-466. 15. W.D. Cheng, D.S. Wu, J. Shen, S.P. Huang, Z. Xie, H. Zhang, Y.J. Gong, From molecule to bulk material: optical properties of hydrogen-bonded dimers [C12H12N4O2AgPF6]2 and [C28H28N6O3AgPF6]2 depend on the arrangement of the oxime moieties, Chem-Eur J. 2007,13 (18), 5151-5159.16. Ohta, K., Higashi, R., Kejima, M.I., Yamamoto, I., Kobayashi, N., Disk-like liquid crystals of transition metal complexes: Critical molecular structure change from columnar to lamellarliquid crystal in bis(diphenylglyoximato)-nickel(II)-based complexes, J. Mater. Chem. 1998, 8, 1979-1991. 17. S. Kumar, R. Singh, H. Singh, Amide–ether–amine-containing macrocycles: synthesis, transport and binding metal cations, J. Chem. Soc. Perkin. Trans. 1999, 1, 3049-3054. 18. Finke, R.G., Schiraldi, D.A., Mayer, B.J., Towards the unification of coenzyme B12-dependent diol dehydratase stereochemical and model studies: The bound radical mechanism, Coord. Chem. Rev. 1984, 54,1-22. 19. Dilworth, J.R., Parrott, S.J., The biomedical chemistry of technetium and rhenium. Chem. Soc. Rev. 1998, 27, 43.20. Chakravorty, A., Structural chemistry of transition metal complexes of oximes, Coord. Chem. Rev. 1974, 13, 1-46.21. Brown, B.G., The chemistry of vitamin B12 and related inorganic model systems. Prog. Inorg. Chem. 1973, 18, 177-286. 22. Thomas, T.W.; Underhill, A.F., Metal–metal interactions in transition-metal complexes containing infinite chains of metal atoms, Chem. Soc. Rew. 1972, 1, 99-120. 23. U. Ocak, Y. Gok, H.B. Senturk, Evaluation of mononuclear Ni(II) complex of a tetra-cryptanded vic-dioxime and its model compound 14-membered N2O2S2 macrobicyclic ligand as Pb 2+, Cd 2+, and Hg 2+ extractants, Sep. Sci. Technol. 2009, 44 (5),1240-1249. 24. Gök, Y., Kantekin, H., Alp, H., Özdemir, M., Synthesis and characterization of the free ligand 5,6:13,14‐dibenzo‐9,10‐benzo(15‐crown‐5)‐2,3‐bis(hydroxyimino)-7,12‐dioxo‐1,4,8,11‐tetraazacyclotetradecane and its mono and trinuclear complexes, Z. Anorg. Allg. Chem. 1995, 621,1237-1242. 25. Durmuş, M., Ahsen,V.,Luneau, D., Pécaut, Synthesis and structures of morpholine substituted new vic-dioxime ligand and its Ni(II) complexes, J. Inorg. Chem. Acta, 2004, 357, 588-594.26. Biyiklioğlu, Z., Dilber, G., Kantekin, H., The synthesis and characterization of a new (e,e)-dioxime and its mono and heterotrinuclear complexes containing dioxadithiadiazamacrobicyclic moieties, transition metal chemistry, Trans. Met. Chem. 2006, 31, 979-985.27. Chandra, S., Kumar, R., Synthesis and spectral studies on mononuclear complexes of chromium(III) and manganese(II) with 12-membered tetradentate N2O2, N2S2 and N4 donor macrocyclic ligands, Trans. Met. Chem. 2004, 29, 269-275.28. Kantekin, H., Ocak, Ü., Gök,Y., Alp, H., Synthesis and characterization of new (E,E)-dioxime and its homo and heterotrinuclear complexes containing dioxadithiadiaza-macrobicycle moiety, Polyhedron 2002, 21, 1865-1870.29. Perrin, D.D., Armarego, W.L.F., Perin, D.R. Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, New York, 1985.30. Gök, Y., Kantekin, H., Synthesis and characterization of novel (E,E)-dioxime and its mono- and heterotrinuclear complexes, Acta Chem. Scand. 1997, 51, 664-671. 31. Pedersen, S.B., Larsen, E., Anti-amphi and cis-trans İsomerisms in some bis-(dioximato)nickel(II) complexes, Acta Chem. Scand. 1973, 27, 3291-3301.32. Nakamura, A., Konishi, A., Otsuka, S., Chiral metal complexes. Part 5. Cobalt(II) and some other transition-metal complexes of chiral vic-dioximate ligands derived from D-camphor and L-β-pinene, J. Chem. Soc. Dalton Trans. 1979, 488-495.33. Gök, Y., Bekaroğlu, Ö., The Synthesis and Complex Formatirn of Stererisomers of some new α-Dioximes, Synth. React. Inorg. Met.-Org. Chem. 1981, 11, 621-631.34. Gök, Y., Kantekin, H., synthesis and characterization of new (e,e)-dioximes and their BF2+-capped mononuclear and trinuclear complexes with Ni(II), Pd(II) and Co(III), New J. Chem. 1995, 19, 461-467.35. Szczepura, L.F., Muller, J.G., Bessel, C.A., See, R.F., Janik, T.S., Churchill, M.R., Takeuchi, K., Characterization of protonated trans bis(dioxime) ruthenium complexes: crystal structures of trans-Ru(DPGH)2(NO)Cl, trans-[Ru(DMGH)(DMGH2)(NO)Cl]Cl, and trans-Ru(DMGH)2(NO)Cl, Inorg. Chem. 1992, 31, 859-869.36. Lance, K.A.; Goldsby, K.A.; Busch, D.H., Effective new cobalt(II) dioxygen carriers derived from dimethylglyoxime by the replacement of the linking protons with difluoroboron(1+), Inorg. Chem. 1990, 29, 4537-4544.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Gülsev Dilber 0000-0001-7114-4421

Halit Kantekin

Yayımlanma Tarihi 31 Aralık 2018
Yayımlandığı Sayı Yıl 2018 Sayı: 3

Kaynak Göster

APA Dilber, G., & Kantekin, H. (2018). Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties. Karadeniz Chemical Science and Technology(3), 12-16.
AMA Dilber G, Kantekin H. Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties. Karadeniz Chem. Sci. Tech. Aralık 2018;(3):12-16.
Chicago Dilber, Gülsev, ve Halit Kantekin. “Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties”. Karadeniz Chemical Science and Technology, sy. 3 (Aralık 2018): 12-16.
EndNote Dilber G, Kantekin H (01 Aralık 2018) Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties. Karadeniz Chemical Science and Technology 3 12–16.
IEEE G. Dilber ve H. Kantekin, “Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties”, Karadeniz Chem. Sci. Tech., sy. 3, ss. 12–16, Aralık 2018.
ISNAD Dilber, Gülsev - Kantekin, Halit. “Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties”. Karadeniz Chemical Science and Technology 3 (Aralık 2018), 12-16.
JAMA Dilber G, Kantekin H. Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties. Karadeniz Chem. Sci. Tech. 2018;:12–16.
MLA Dilber, Gülsev ve Halit Kantekin. “Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties”. Karadeniz Chemical Science and Technology, sy. 3, 2018, ss. 12-16.
Vancouver Dilber G, Kantekin H. Synthesis And Characterization Of A New (E, E)-Dioxime And Its Mono Nuclear Nickel (II) Complex Containing Diazatetrathidioxa Macrobicyclic Moieties. Karadeniz Chem. Sci. Tech. 2018(3):12-6.