Hidrazon Grubu Taşıyan vic-Dioksim Türevlerinin ve Onların Metal Komplekslerinin Sentezi ve Spektrofotometrik İncelemesi

Year 2017, Volume: 7 Issue: 4, 161 - 168, 31.12.2017

Nursabah Sarıkavaklı

Abstract

Bu çalışmada, hidrazon ve vic-dioksim grubu içeren; (1Z,2E)-N’-[(1Z)-(4-bromofenil)metilen]-2-

(hidroksiimino)etanhidroksimhidrazid, L1H2, (1Z,2E)-N’-[(1Z)-(2-klorofenil)metilen]-2-(hidroksiimino)

etanhidroksimhidrazid, L2H2, (1Z,2E)-N’-[(1Z)-(3-klorofenil)metilen]-2-(hidroksiimino)etanhidroksimhidrazid,

L3H2 hidrazonoksim türevleri elde edilmiştir. Bu hidrazonoksim bileşikleri [(1Z,2E)-2-(hidroksiimino)

etanhidroksimhidrazid]’in aldehit ve ketonlarla verdiği kondenzasyon reaksiyonu ile sentezlenmiştir. Elde edilen

hidrazonoksim türevlerinin nikel(II), bakır(II), kobalt(II) kompleksleri izole edildikten sonra hem ligandların hem

de komplekslerin yapıları elementel analiz, manyetik süsseptibilite, erime noktası, 1H-NMR, 13C-NMR, UV-Vis,

FT-IR, TGA-DTG ile karakterize edildi.

Keywords

FTIR, hidrazonoksim, kompleks, NMR, vic-dioksim

Synthesis and Spectrophotometrical Investigation of vic-Dioxim Derivatives Bearing Hydrazone Group and Their Metal Complexes

Abstract

In this work an attempt has been to explore some important characteristics of the hydrazoneoxime

derivatives bearing hydrazone and vic-dioxime group, which were obtained from the materials such as: (1Z,2E)-

N’-[(1Z)-(4-bromophenyl)methylene]-2-(hydroxyimino)ethanehydroximohydrazide, L1H2, (1Z,2E)-N’-[(1Z)-(2-

chlorophenyl)methylene]-2-(hydroxyimino)ethanehydroximohydrazide, L2H2, (1Z,2E)-N’-[(1Z)-(3-chlorophenyl)

methylene]-2-(hydroxyimino)ethanehydroximohydrazide, L3H2. All these hydrazoneoxime compounds were

synthesized in terms of the reaction condensation of GH2, [(1Z,2E)-2-(hydroxyimino)ethanehydroximohydrazide]

with aldehydes and ketones. It has been found that some of complexes; e.g. nickel(II), copper(II), cobalt(II) from

the hydrazone-oxime derivatives have been isolated, and the structures of both ligands and complexes were

characterized by various techniques; by elemental analysis, magnetic susceptibility, melting point, 1H-NMR,

13C-NMR, UV-Vis, FT-IR and TGA-DTG.

Keywords

FTIR, hydrazoneoxime, complex, NMR, vic-dioxime

References

• Angela S, Galiano-Roth A, Collum DB, 1988. 6Li and 23Na NMR spectroscopic studies of metalated hydrazone cryptates. Effects of ion triplet formation on the stereochemistry of alkylation. J. Am. Chem. Soc., 110: 3546-3553.
• Canpolat E, Kaya M, 2004. The synthesis and characterization of N-{2-[(1,4-dioxaspiro[4.5]-dec-2-ylmethyl)amino]ethyl}-N′- hydroxy-2-(hydroxyimino)ethanimidamide and some of its transition metal complexes. Journal of Coordination Chemistry, 57 (1): 25-32.
• Canpolat E, Kaya M, Yazıcı A, 2004. Synthesis and characterization of Co(II), Ni(II), Cu(II), and Zn(II) complexes with a new vic-dioxime (E,E)-N'-hydroxy-2-(hydroxyimino)-N-(4-{[(2-phenyl-1,3-dioxolan-4yl)methyl]amino}butyl)ethanimidamide. Russian Journal of Coordination Chemistry, 30(2):87–93.
• Canpolat E, Kaya M,. Bakırdere E G, 2005. Synthesis and characterization of mononuclear cadmium(II) and dinuclear uranyl(VI) complexes with vic-dioximes. Transition Met. Chem., 30:503-507.
• Chakravorty A, 1974. Structure chemistry of transition metals complexes of oximes. Coordination Chemistry Reviews, 13(1): 1-46.
• Durmuş M, Ahsen V, Luneau D, Pecaut J, 2004. Synthesis and structures of morpholine substituted new vic-dioxime ligand and its Ni(II) complexes. Inorg. Chim. Acta., 357: 588-594.
• Ertaş M, Ahsen V, Gül A, Bekaroğlu Ö, 1987. Synthesis of bis(ferrocenylamino)glyoxime and its nickel(II) complexes. J. of Organometallic Chem., 333(3):383-385.
• Galiano-Roth A, Collum DB, 1988. Lithium-6 and sodium-23 NMR spectroscopic studies of metalated hydrazone cryptates. Effects of ion triplet formation on the stereochemistry of alkylation. J. Am. Chem. Soc., 110: 3546-3553.
• Güp R., Bedük A D, 2002. Synthesis and characterization of complexes of Ni(II), Co(II), and Cu(II) with four 4-aminobenzoate derivatives of unsymmetrical vic-dioximes. Synth. React. Inorg. Met.-Org. Chem., 32: 1043-1055.
• Gürsoy S, Koçak M, Cihan A, Gül A, Bekaroğlu Ö, 2000. Synthesis and complexation of a novel soluble vic-dioxime with hydroxyethyl pendant arms. Transition metal chemistry, 25 (4): 474-477.
• Herac R, Prelesnik B, Leova V, Chundak S, 1991. Transition metal complexes with hydrazides and hydrazones. IV. Structure of trans-diammine[2,3-butanedione bis(4-methoxybenzoylhydrazonato)]cobalt(III) nitrate monohydrate. Acta Cryst., 47:1408-1411.
• Karadeniz K, Bekaroğlu Ö, 1983. The synthesis and complex formation of four new macrocyclic vic-dioximes. Synth. React. Inorg. Met.-Org. Chem., 13: 1029-1045.
• Karataş I, İrez G, Sezgin M, Uçan H I, Bedük A D, 1991. The synthesis of some new bis(1,2-dioximes) and their polymeric metal complexes. Synth. React. Inorg. Met.-Org. Chem., 21(67): 1031-1040.
• Karataş I, Uçan H I, 1998. The synthesis of biphenylglyoxime and bis (phenylglyoxime) and their complexes with Cu(II), Ni(II) and Co(II). Synth. React. Inorg. Met.-Org. Chem., 28(3): 383-391.
• Kurtoğlu M, Ispir E, Kurtoğlu N, Serin S, 2008. Novel vic-dioximes: Synthesis, complexation with transition metal ions, spectral studies and biological activity. Dyes and Pigments, 77: 75-80.
• Kurtoğlu M, Serin S, 2002. 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., 32(3): 629-637.
• Özcan E, Karapınar E, Karapınar N. 2001. The synthesis and Ni(II), Co(II), Cu(II), Cd(II), and Zn(II) complexes of two new unsymmetrical vic-dioximes. Synth. React. Inorg. Met.-Org. Chem., 31(7): 1163-1174.
• Özkan E, Canpolat E, Kaya M, 2005. Synthesis of new glyoxime derivatives, characterization and investigation of their complexes with Co (II), Ni (II), and Cu (II) metals and thermal studies. Russian Journal of Coordination Chemistry, 31(7): 506-510.
• Raper ES, 1985. Complexes of heterocyclic thione donors. Coordination Chemistry Reviews, 61:115-184.
• Saleh AA; Khalik SME, Eid MF, El-Ghamry MA, 2003. Synthesis, spectral and magnetic studies of mononuclear and binuclear Mn(II), Co(II), Ni(II) and Cu(II) complexes with semicarbazone ligands derived from sulfonamide. J. Coor. Chem., 56: 467-480.
• Sarıkavaklı N, İrez G, 2005. Synthesis and complex formation of some novel vic-dioxime derivatives of hydrazones. Turk J Chem., 29: 107-115.
• Selwood PW, 1956. Magnetochemistry Interscience Publishers Inc., 2nd ed., New York.
• Wilkinson G, Gillard RD, Cleverly Mc, eds., 1987. Comprehensive Coordination Chemistry. Pergamon Press, Oxford, 2: 715-738.