The Novel bis-dioxime-based and Boronic acid-capped Groups Containing Fe(II) and Co(II) Complexes: Synthesis, Characterization, and Spectroscopy

Yıl 2017, Cilt: 4 Sayı: 1, 11 - 22, 13.07.2017

Ahmet Kılıç Adem Erdoğan Mustafa Durgun

https://doi.org/10.18596/jotcsa.318141

Öz

In the present work, firstly the novel mono oxime (1) and asymmetric dioxime ligand (LH₂) (2) derived 4′-hydroxyvalerophenone as ketone were prepared under optimum conditions. Then,
the bis-dioxime-based and boronic acid-capped groups containing Fe(II) and
Co(II) complexes [(L)₂M(X)₂(BA)₂]
(3-6) (L= Dioxime, M = Fe(II) or
Co(II), X= Cl₂ or H₂O and BA = Butyl boronic acid (BBA)
or Ferrocene boronic acid (FBA)) were synthesized in a two-necked round-bottom
reaction flask by direct contact of dioxime ligand (2),
and different boronic acid with metal salts (FeCl₂.4H₂O
or CoCl₂) without special requirement of any additional
chemical process. The prepared ligands and its Fe(II)
and Co(II) complexes were characterized by means of NMR spectra, FT-IR spectra,
UV-Vis spectra, LC-MS, melting point and magnetic susceptibility measurements as well as elemental
analysis. The spectroscopic results demonstrated that the proposed Fe(II) and
Co(II) complexes are a six-coordinated species and octahedral geometry. The
infrared spectra (FT-IR) of the Fe(II) and Co(II) complexes indicated the
characteristic peak at range 1208-1217 cm^-1 cm corresponding υ(B-O)
stretching.

Anahtar Kelimeler

Bis-dioximates, Fe(II) and Co(II) complexes, spectroscopy, boronic acid

Kaynakça

• 1. Whyte AM, Roach B, Henderson DK, Tasker PA, Matsushita MM, Awaga K, Robertson N. Structural, magnetic, and electronic properties of phenolic oxime complexes of Cu and Ni. Inorganic chemistry. 2011 Dec; 50(24):12867-76. DOI: 10.1021/ic2020644.
• 2. Kelley P, Day MW, Agapie T. Hydrogen Evolution Catalyzed by Aluminum-Bridged Cobalt Diglyoximate Complexes. Inorg. Che. 2013 Aug; 2013(22-23:)3840–45. DOI: 10.1002/ejic.201300309.
• 3. Kilic A, Tas E, Yilmaz I. Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of 𝑁,𝑁'-(4-amino-1-benzyl piperidine)-glyoxime J. Chem. Sci. 2009 Jan; 121(1): 43-56. http://www.ias.ac.in/article/fulltext/jcsc/121/01/0043-0056.
• 4. Kilic A, Yilmaz I, Ulusoy M, Tas E. Synthesis, spectral characterization, electrochemical studies and catalytic properties in Suzuki–Miyaura coupling reactions of the mononuclear PdII, trinuclear PdII(BPh2)2 and RuII PdII RuII type complexes containing 4-amino-1-benzyl piperidine and phenyl groups. Applied Organometallic Chemistry. 2008 Sep; 22(9): 494-502. DOI:10.1002/aoc.1430.
• 5. Al-Obaidi FN, Atabey H, Macit M, Sari H. Potentiometric and Theoretical Studies of (2Z, 3Z)-2H-benzo[b][1,4]thiazine-2,3(4H)-dionedioxime with Some Divalent Transition Metal Ions. Journal of Solution Chemistry. 2014 May; 43(5):989-999. DOI: 10.1007/s10953-014-0176-1
• 6. Nakamura A, Konishi A, Ostuka 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. Dalton Transactions. 1979; 3: 488-495. DOI: 10.1039/DT9790000488.
• 7. Babahan I, Ozmen A, Orhan N, Kazar D, Degirmenci EH. Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes. Bioorganic Chemistry. 2014 Apr; 53:92-98. DOI: 10.1016/j.bioorg.2014.01.003.
• 8. Mitchell P. Keilin's Respiratory Chain Concept and Its Chemiosmotic Consequences. Science. 1979 Dec; 206:1148-59.Science1979,206, 1148-1159. http://www.jstor.org/stable/1749145.
• 9. Cervara B, Ruiz R, Lloret F, Julve M, Faus J, Munoz MC, Journnaux Y. Interaction between heterobinuclear molecules and nature of the ground spin state in oximato-bridged [CuIIMII]2 bis-binuclear complexes (M=Cu, Ni, Mn): crystal structure of [Cu(pdmg)Ni(Me3[12]N3)(EtOH)](ClO4)2. Inorganica Chimica Acta. 1999 May; 288(1): 57–68. DOI: 10.1016/S0020-1693(99)00035-3.
• 10. Herron N, Busch DH. Reversible Dioxygen Binding by a Totally Synthetic Non-Porphyrin Macrobicyclic Iron(I1) Complex Containing a Persistent Void. Journal of the American Chemical Society. 1981 Nov; 103(5):1236-37. DOI:10.1021/ja00395a050.
• 11.Earnshaw A, editor. Introduction to Magnetochemistry:Chapter 1. London: Academic Press; 1968. 126 p. ISBN: 9781322266435.
• 12. Kilic A, Tas E, Gumgum B, Yilmaz I. Synthesis, spectral characterization and electrochemical properties of new vic-dioxime complexes bearing carboxylate. Transition Metal Chemistry.2006 Aug;31(5):645-652. DOI: 10.1007/s11243-006-0043-z.
• 13. Kilic A, Kilic MV, Ulusoy M, Durgun M, Aytar E, Dagdevren M, Yilmaz I. Ketone synthesized cobaloxime/organocobaloxime catalysts for cyclic carbonate synthesis from CO 2 and epoxides: Characterization and electrochemistry. 2014 Sep;767 (2014):150-159. DOI: 10.1016/j.jorganchem.2014.05.023.
• 14.Artyushin OI, Matveeva EV, Vologzhanina AV, Voloshin YZ. Clathrochelates meet phosphorus. New thio-and phosphorylation reactions of an iron (II) dichloroclathrochelate precursor and preparation of its first phosphorus (III)-containing macrobicyclic derivative. Dalton Transactions. 2016 Feb;45(12): 5328-5333. DOI:10.1039/C6DT00164E.
• 15. Gupta BD, Qanungo K. Pyrazine bridged organodicobaloximes: a convenient one pot synthesis and cis influence studies. Journal of Organometallic Chemistry. 1998 Apr;557(2): 243–249. DOI: 10.1016/S0022-328X(97)00777-8.
• 16.Yamuna R, Sarath S, Kubandiran K, Umadevi M, Chakkaravarthi G. Synthesis, characterization and thermal studies of 1, 3-bis (4-pyridyl) propane bridged dicobaloximes. Journal of Organometallic Chemistry.2016 Jun ;811:40-47. DOI:10.1016/j.jorganchem.2016.03.015.
• 17. Wani MY, Kumar S, Arranja CT, Dias CMF, Sobral AJFN. Cycloaddition of CO 2 to epoxides using di-nuclear transition metal complexes as catalysts. New Journal of Chemistry. 2016 Mar ;40(6):4974-4980. DOI: 10.1039/C5NJ03198B.