Spectroscopic Characterization of N,N-bis(2-{[(2,2-Dimethyl-1,3-Dioxolan-4-yl)Methyl]Amino}Ethyl) N′,N′-Dihydroxyethanediimidamide and Its Complexes

Abstract

1 Transition metal complexes of vic -dioximes have been of particular interest as biological model compounds [1]. The high stability of the complexes prepared with dioxime ligands has been extensively used for various purposes including model compounds for vitamin B 12 or trace metal analysis [2]. Coordination compounds of vic -dioximes have been widely investigated as analytical reagents, models for biological systems, such as vitamin B 12 , compounds having columnar stacking thought to be a reason for their semiconducting properties, and recently in dioxime reactions [3]. Among three isomers, namely, anti, amphi , and syn , the first isomer is more liable to form N,N-coordinated planar complexes stabilized by hydrogen bonding [4]. The presence of mildly acidic hydroxyl groups and slightly basic nitrogen atoms make vic -dioximes amphoteric ligands forming corrin-type, square planar, square pyramidal, and octahedral complexes with transition metal ions, such as Co 2+ , Ni 2+ , Cu 2+ , and Co 3+ as central atoms [5].The chemistry of oxime/oximato metal complexes has been developed actively since the time of the first synthesis, e.g. preparation of nickel(II) dimethylglyoximate, and recognition of the chelate five-membered character of this complex by Chugaev [6]. Coordinated oxime ligands and oxime complexes display an impressively rich variety of reactivity modes and give unusual types of chemical compounds [7]. Some recently 1 The text was submitted by the authors in English. reviewed data show that oximes, although being classical ligands [8], display a variety of reactivity modes unusual even for the modern coordination chemistry [9, 10].We have focused on the synthesis and characterization of various types of vic -dioximes and their transition metal complexes [11][12][13][14][15][16][17][18][19]. The aim of this work is the synthesis and characterization of the dioxime ligand and its Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , and Cd 2+ metal complexes. EXPERIMENTALThe preparation of ( E , E )-dichloroglyoxime has been described previously [20]. All the reagents used were purchased from Merck, Fluka, or Sigma and are chemically pure.Elemental analyses (C, H, N) were performed on a LECO-932 CHNSO elemental analyses apparatus. IR spectra were recorded on a Mattson 1000 FT-IR spectrometer with KBr pellets. 1 H and 13 C NMR spectra were recorded on a Bruker GmbH Dpx-400 MHz high performance digital FT-NMR spectrometer (in DMSO-d 6 ). Electronic spectra were obtained on a Shimadzu 1240 UV spectrometer. Magnetic susceptibilities were determined on a Sherwood Scientific magnetic susceptibility balance (Model MK1) at room temperature using Hg [ Co ( SCN ) 4 ] as a calibrate; diamagnetic corrections were calculated from Pascal's constants. Melting points were determined on a Gallenkamp melting point apparatus. Molar conductances of the dioxime ligand and its Abstract -A new dioxime ligand, N , N -bis (2-{[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]amino}ethyl) N ', N '-dihydroxyethanediimidamide (H 2 L), and its mononuclear complexes...

Thermal, Electrical, and Optical Properties of Synthesized (1E, 2E)‐(4‐bromophenyl)(hydroxyimino)acetaldehyde Oxime Complexes

“…The mononuclear complex of Ni(II) is diamagnetic, while Co(II) and Cu(II) are paramagnetic. According to the literature, square-planer geometry of the structure of the Ni(II), Co(II), and Cu(II) complexes may be reasonable [29,[31][32][33].…”

“…The inflation of the t.g.a. curves of all the complexes at a temperature below 800 ∘ C indicates the decomposition of the fully organic part of the chelate, leaving the metallic oxide at the final temperature [33,35,36].…”

Synthesis, Electrochemical and Luminescence Studies of Nickel and Vanadium Complexes Containing Tetradentate Schiff Base Ligand with N2O2 Donor Atoms

“…28,29 A weak broadband in 3421 cm -1 due to the OH group in the free Schiff base ligand was not observed in the infrared spectra of the nickel and vanadyl complexes which indicated that phenolic oxygen was deprotonated and coordinated in two complexes. 30 Additional support for the formation of the complexes were provided by the existence of weak intensity bands at around 504-691 cm -1 region which were attributed to the formation of M-N and M-O, respectively. These variations confirmed the coordination of nickel with the azomethine nitrogen and phenolic oxygen of the Schiff base.…”

Synthesis, Characterization, Analytical and Cytotoxic Studies of N,N′‐Bis(2‐Hydroxynaphthylidene)‐4‐chlorophenyl Methanediamine and Its Co(II), Ni(II) and Cu(II) Complexes

“…The spectra exhibit the azomethine À C=N À carbon at 131.54 ppm. [18] The phenolic carbons appear in the range of 150.80 ppm. [18] The chemical shift of aromatic carbons appears in the range from 113.50 ppm to 131.09 ppm.…”