Multidentate chelating agents from Quinoline-8-aldehyde. I. Tridentate and quadridentate Schiff bases from primary diamines

1966 ◽  
Vol 19 (12) ◽  
pp. 2241 ◽  
Author(s):  
J Dekkers ◽  
HA Goodwin

Complexes of 1,2-bis(8-quinolylmethyleneimino)ethane with cobalt(II), nickel(II), and copper(II) are described. The copper complexes are five-covalent and, it is suggested, trigonal bipyramidal. Reaction of the Schiff base with iron(II), cobalt(III), and, under certain conditions, nickel(II) leads to its partial hydrolysis, and complexes of the tridentate 1-amino-2-(8-quinolylmethyleneimino)ethane are obtained. The hydrolysis of the Schiff base in the presence of metal ions is discussed in terms of steric effects within the base and of the stereochemical demands of the metal ions. Complexes of 1,2-bis(8-quinolylmethyleneimino)benzene and its hydrolysis derivative 1-amino-2-(8-quinolylmethyleneimino)ethane are also described.

2012 ◽  
Vol 77 (11) ◽  
pp. 1589-1597 ◽  
Author(s):  
Maryam Lashanizadegan ◽  
Marzieh Sarkheil

The Schiff base ligand trans-N,N?-bis[2-pyridinecarboxylidene] cyclohexane-1,2-diamine (L) was synthesized. This ligand when stirred with 1 equiv of MCl2.xH2O (M = Cu, Co, Zn) in ethanol, undergoes partial hydrolysis of the imino bond and the result tridentate ligand (L') and immediately forms the complexes with N3 coordination sphere. The reactions of L with MCl2.xH2O (M = Cu, Co, Zn) in THF give complexes [ML]Cl2. The ligand (L), complexes [M(L')Cl]Cl and [ML]Cl2 were characterized by elemental analysis, UV-Vis, FT-IR, 1H NMR, GC/MS and luminescence properties. The 1H NMR spectra of the ligand and its diamagnetic complexes were recorded in CDCl3 and DMSO solvents, respectively. Obtained data confirm that the donor atoms N in ligand coordinated to the metal ions. The luminescence studies show ligands and their complexes display intraligand (?- ?


1980 ◽  
Vol 58 (7) ◽  
pp. 727-732 ◽  
Author(s):  
M. Akbar Ali

New Schiff base ligands formed from 2-methoxybenzaldehyde and 2,4-dimethoxybenzaldehyde with N-methyl-S-alkyldithiocarbazates and their nickel(II) and copper(II) complexes have been prepared and characterised by elemental analysis and magnetic and spectroscopic measurements. The Schiff bases behave as neutral tridentate chelating agents forming stable nickel(II) complexes of stoichiometry NiLX2•xC2H5OH (L = 2-methoxy- or 2,4-dimethoxybenzaldehyde Schiff bases of N-methyl-S-methyldithiocarbazate; X = I−, SCN−; x = 0, 1). Conductivity, magnetic, and spectral data support an octahedral structure for the nickel(II) complexes. The CuLCl2 complexes were also isolated. Magnetic and spectral evidence are in accord with a chloro-bridged dimeric structure. The chloro-complex of copper(II) with the 2-methoxybenzaldehyde Schiff base displays a room-temperature magnetic moment of 1.81 BM, which remains virtually constant over the temperature range 343–123 K.Hydrated copper(II) chloride promotes complete hydrolysis of the 2,4-dimethoxybenzaldehyde and 2-methoxybenzaldehyde Schiff bases of N-methyl-S-benzyldithiocarbazate with the concomitant formation of copper(II) complexes of the parent N-methyl-S-benzyldithiocarbazate of general formula, Cu(N—SR)Cl2 (R = C6H5CH2—).


1972 ◽  
Vol 8 (1-2) ◽  
pp. 55 ◽  
Author(s):  
E.C. Lingafelter ◽  
L.C. Andrews ◽  
R.M. Kirchner ◽  
N.J. Rose ◽  
L.J. Wilson

1969 ◽  
Vol 22 (8) ◽  
pp. 1613 ◽  
Author(s):  
PSK Chia ◽  
SE Livinhstone

Mono-ligand complexes of 6-methylpyrid-2-yl-N-(2?-methylthiophenyl)- methyleneimine (SNSMe) of the type MX2(SNNMe) (M = Mn, Fe, Co, Xi, and Cu; X = Cl, Br, I, or NCS) have been prepared. Infrared data show that in all the complexes the ligand (SNNMe) is tridentate. The electronic and infrared spectra indicate that the complexes of manganese, iron, and cobalt are five-coordinate, whereas the nickel and copper complexes are six-coordinate and polymeric. The complex CO(NO3)2(SNNMe) is six- coordinate and contains one bidentate and one unidentate nitrato group. ��� The bis-ligand complexes [N(SNNMe)2]Y2 (M = Fe, Ni, and Cu; Y = ClO4 or BF4) were also isolated. The iron complex is low-spin (μ 1.5 B.M.) but the magnetic moment of the nickel complex (μ 3.0 B.M.) is normal for high-spin octahedral nickel(II).


2021 ◽  
Vol 11 (4) ◽  
pp. 3989-4006

In the present research, a series of Ce+3 metal ions complexation with INZ incorporating Schiff bases have been reported. INZ incorporated Schiff Bases (3a-e) were developed by condensing INZ with substituted aromatic aldehyde and confirmed with various spectral Techniques such as Elemental analysis, UV, IR, 1H-NMR, 13H NMR. All the synthesized organic ligands were evaluated against antibacterial and antifungal stains and found moderate to significant results. The Ce+3 metal ion solution mixed with newly prepared bio-active INZ Schiff bases (3a-e) to afford the [Ce-INZ Schiff Base] complexes (4a-e). The stability constants of prepared complexes were evaluated and found in order as a (3e) > (3d) > (3a) > (3b) > (3c).


2019 ◽  
Vol 43 (13) ◽  
pp. 5139-5149 ◽  
Author(s):  
Atanu Panja ◽  
Kumaresh Ghosh

The cholesterol appended hydroxybenzaldehyde derived Schiff bases1–4have been designed and synthesized. They are suitable for the naked-eye detection of metal ions such as Hg2+and Ag+using sol–gel methodology involving either rupturing or maintaining the imine bonds.


RSC Advances ◽  
2020 ◽  
Vol 10 (39) ◽  
pp. 23372-23378
Author(s):  
Aiying Han ◽  
Hao Su ◽  
Guohong Xu ◽  
Maroof Ahmad Khan ◽  
Hui Li

Acylhydrazone Schiff bases are rich in N and O atoms to coordinate with metal ions to form multidentate complexes.


2016 ◽  
Vol 72 (3) ◽  
pp. 239-242
Author(s):  
Kazem Barati ◽  
William Clegg ◽  
Mohammad Hossein Habibi ◽  
Ross W. Harrington ◽  
Arash Lalegani ◽  
...  

Transition metal complexes of Schiff base ligands have been shown to have particular application in catalysis and magnetism. The chemistry of copper complexes is of interest owing to their importance in biological and industrial processes. The reaction of copper(I) chloride with the bidentate Schiff baseN,N′-bis(trans-2-nitrocinnamaldehyde)ethylenediamine {Nca2en, systematic name: (1E,1′E,2E,2′E)-N,N′-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]} in a 1:1 molar ratio in dichloromethane without exclusion of air or moisture resulted in the formation of the title complex μ-chlorido-μ-hydroxido-bis(chlorido{(1E,1′E,2E,2′E)-N,N′-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]-κ2N,N′}copper(II)) dichloromethane sesquisolvate, [Cu2Cl3(OH)(C20H18N4O4)2]·1.5CH2Cl2. The dinuclear complex has a folded four-membered ring in an unsymmetrical Cu2OCl3core in which the approximate trigonal bipyramidal coordination displays different angular distortions in the equatorial planes of the two CuIIatoms; the chloride bridge is asymmetric, but the hydroxide bridge is symmetric. The chelate rings of the two Nca2en ligands have different conformations, leading to a more marked bowing of one of the ligands compared with the other. This is the first reported dinuclear complex, and the first five-coordinate complex, of the Nca2en Schiff base ligand. Molecules of the dimer are associated in pairs by ring-stacking interactions supported by C—H...Cl interactions with solvent molecules; a further ring-stacking interaction exists between the two Schiff base ligands of each molecule.


2020 ◽  
Vol 21 (2) ◽  
pp. 555 ◽  
Author(s):  
Sokratis T. Tsantis ◽  
Demetrios I. Tzimopoulos ◽  
Malgorzata Holynska ◽  
Spyros P. Perlepes

Even 155 years after their first synthesis, Schiff bases continue to surprise inorganic chemists. Schiff-base ligands have played a major role in the development of modern coordination chemistry because of their relevance to a number of interdisciplinary research fields. The chemistry, properties and applications of transition metal and lanthanoid complexes with Schiff-base ligands are now quite mature. On the contrary, the coordination chemistry of Schiff bases with actinoid (5f-metal) ions is an emerging area, and impressive research discoveries have appeared in the last 10 years or so. The chemistry of actinoid ions continues to attract the intense interest of many inorganic groups around the world. Important scientific challenges are the understanding the basic chemistry associated with handling and recycling of nuclear materials; investigating the redox properties of these elements and the formation of complexes with unusual metal oxidation states; discovering materials for the recovery of trans-{UVIO2}2+ from the oceans; elucidating and manipulating actinoid-element multiple bonds; discovering methods to carry out multi-electron reactions; and improving the 5f-metal ions’ potential for activation of small molecules. The study of 5f-metal complexes with Schiff-base ligands is a currently “hot” topic for a variety of reasons, including issues of synthetic inorganic chemistry, metalosupramolecular chemistry, homogeneous catalysis, separation strategies for nuclear fuel processing and nuclear waste management, bioinorganic and environmental chemistry, materials chemistry and theoretical chemistry. This almost-comprehensive review, covers aspects of synthetic chemistry, reactivity and the properties of dinuclear and oligonuclear actinoid complexes based on Schiff-base ligands. Our work focuses on the significant advances that have occurred since 2000, with special attention on recent developments. The review is divided into eight sections (chapters). After an introductory section describing the organization of the scientific information, Sections 2 and 3 deal with general information about Schiff bases and their coordination chemistry, and the chemistry of actinoids, respectively. Section 4 highlights the relevance of Schiff bases to actinoid chemistry. Sections 5–7 are the “main menu” of the scientific meal of this review. The discussion is arranged according the actinoid (only for Np, Th and U are Schiff-base complexes known). Sections 5 and 7 are further arranged into parts according to the oxidation states of Np and U, respectively, because the coordination chemistry of these metals is very much dependent on their oxidation state. In Section 8, some concluding comments are presented and a brief prognosis for the future is attempted.


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