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Inorganics
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Synthesis, Structure and Properties of Schiff Base Metal Complexes
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Synthesis, Structure and Properties of Schiff Base Metal Complexes

A special issue of Inorganics (ISSN 2304-6740). This special issue belongs to the section "Coordination Chemistry".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 15641

Special Issue Editors

Prof. Dr. Bi-Xue Zhu

E-Mail Website
Guest Editor
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China
Interests: Schiff base complexes; Schiff base macrocycles; self-assembly; organic particles
Dr. Chao Huang

E-Mail Website
Guest Editor
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China
Interests: Schiff base complex; acylhydrazone; chiral self-assembly; coordination polymer

Special Issue Information

Dear Colleagues,

Schiff bases, named after the German chemist Hugo Schiff, are a unique class of compounds with different donor atoms that exhibit fascinating coordination style towards numerous metal ions. They are important due to their ability to stabilize metal ions of various oxidation states, participate in numerous catalytic and industrial applications, and display broad-spectrum biological activities. Schiff base metal complexes are well-known for their easy synthesis and wide application. Metal complexes containing Schiff base ligands have been extensively studied for their interesting and important properties in the past several decades. In this Special Issue, we wish to cover the most recent advances in all these aspects of Schiff base metal complexes by hosting a mix of original research articles and short critical reviews.

Prof. Dr. Bi-Xue Zhu
Dr. Chao Huang
Guest Editors

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Keywords

  • Schiff base complexes
  • metal coordination chemistry
  • crystal structure
  • molecular self-assembly
  • chemical property

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Published Papers (6 papers)

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Research

19 pages, 4185 KiB  
Article
Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center
by Greg Brewer, Cynthia Brewer, Raymond J. Butcher and Peter Zavalij
Inorganics 2023, 11(10), 381; https://doi.org/10.3390/inorganics11100381 - 25 Sep 2023
Cited by 1 | Viewed by 2118
Abstract
The Schiff base reaction of imidazole-2-carboxaldehydes with the anion of alanine, leucine and phenylalanine in the presence of nickel(II) ion gives the neutral NiL2 complexes. The Schiff base ligand, L, binds through an imidazole nitrogen, NIm, the amino acid nitrogen, [...] Read more.
The Schiff base reaction of imidazole-2-carboxaldehydes with the anion of alanine, leucine and phenylalanine in the presence of nickel(II) ion gives the neutral NiL2 complexes. The Schiff base ligand, L, binds through an imidazole nitrogen, NIm, the amino acid nitrogen, NAA, and a carboxylate oxygen, O, atom. The two N2O ligands bind to the nickel(II) in a meridional fashion with the NIm and O of each ligand in trans positions. These ligands can exist as the anticipated aldimine, Im − CH = NAA − CH(R) − CO2−, or the ketimine, Im − CH2NAA = C(R) − CO2−, tautomer. Tautomerization of the initially formed aldimine Schiff base results in movement of the hydrogen atom of the alpha carbon of the amino acid to the aldehyde carbon, CAld, atom of the imidazole carboxaldehyde with resultant relocation of the imine double bond in the reverse direction. Ten structures of the structurally unprecedented ketimine tautomer, prepared from imidazole-2-carboxaldehydes and a pyrazole-3-carboxaldehyde, were presented. The structural data supported the formation of the ketimines in each case, while the aldimine tautomer was observed with imidazole-4-carboxaldehydes. A rationale of this can be explained on the basis of charge distribution in the likely intermediate in the tautomerization. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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11 pages, 3928 KiB  
Article
In-Situ EC-AFM Study of Electrochemical P-Doping of Polymeric Nickel(II) Complexes with Schiff base Ligands
by Evgenia Smirnova, Alexander Ankudinov, Irina Chepurnaya, Alexander Timonov and Mikhail Karushev
Inorganics 2023, 11(1), 41; https://doi.org/10.3390/inorganics11010041 - 14 Jan 2023
Cited by 3 | Viewed by 1732
Abstract
Conductive electrochemically active metallopolymers are outstanding materials for energy storage and conversion, electrocatalysis, electroanalysis, and other applications. The hybrid inorganic–organic nature of these materials ensures their rich chemistry and offers wide opportunities for fine-tuning their functional properties. The electrochemical modulation of the nanomechanical [...] Read more.
Conductive electrochemically active metallopolymers are outstanding materials for energy storage and conversion, electrocatalysis, electroanalysis, and other applications. The hybrid inorganic–organic nature of these materials ensures their rich chemistry and offers wide opportunities for fine-tuning their functional properties. The electrochemical modulation of the nanomechanical properties of metallopolymers is rarely investigated, and the correlations between the structure, stiffness, and capacitive properties of these materials have not yet been reported. We use electrochemical atomic force microscopy (EC-AFM) to perform in-situ quantitative nanomechanical measurements of two Schiff base metallopolymers, poly[NiSalphen] and its derivative that contains two methoxy substituents in the bridging phenylene diimine unit poly[NiSalphen(CH3O)2], during their polarization in the electrolyte solution to the undoped and fully doped states. We also get insight into the electrochemical p-doping of these polymers using electrochemical quartz crystal microgravimetry (EQCM) coupled with cyclic voltammetry (CV). Combined findings for the structurally similar polymers with different interchain interactions led us to propose a correlation between Young’s modulus of the material, its maximum doping level, and ion and solvent fluxes in the polymer films upon electrochemical oxidation. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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20 pages, 3232 KiB  
Article
Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens
by Amira A. Mohamed, Fatma M. Ahmed, Wael A. Zordok, Walaa H. El-Shwiniy, Sadeek A. Sadeek and Hazem S. Elshafie
Inorganics 2022, 10(11), 177; https://doi.org/10.3390/inorganics10110177 - 25 Oct 2022
Cited by 21 | Viewed by 1966
Abstract
Condensation of the reaction between enrofloxacin and ethylenediamine in the existence of glacial acetic acid produced a new N,N-ethylene (bis 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid Schiff base (H2Erx-en). H2Erx-en was used as a tetra-dentate ligand to produce novel complexes by [...] Read more.
Condensation of the reaction between enrofloxacin and ethylenediamine in the existence of glacial acetic acid produced a new N,N-ethylene (bis 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid Schiff base (H2Erx-en). H2Erx-en was used as a tetra-dentate ligand to produce novel complexes by interacting with metal ions iron(III), yttrium(III), zirconium(IV), and lanthanum(III). The synthetic H2Erx-en and its chelates had been detected with elemental analysis, spectroscopic methods, mass spectrometry, thermal studies, conductometric and magnetic measurements experiments. The calculated molar conductance of the complexes in 1 × 10−3 M DMF solution shows that iron(III), yttrium(III) and lanthanum(III) are 1:1 electrolytes, however the zirconium(IV) complex is non-electrolyte. The infrared spectra of H2Erx-en chelates indicated that the carboxylic group is deprotonated and H2Erx-en is associated with metals as a tetra-dentate through nitrogen and oxygen atoms. The disappearance of the carboxylic proton in all complexes corroborated information concerning H2Erx-en deprotonation and complexation with metal ions, according to 1H NMR data. Thermal analysis revealed the abundance of H2O particles in the chelates’ entrance and outlet spheres, indicating the disintegration pattern of H2Erx-en and their chelates. The Coats–Redfern and Horowitz–Metzeger approaches were utilized to calculate the thermodynamic items (Ea, ΔS *, ΔH *, and ΔG *) at n = 1 and n ≠ 1. The resulting data reveal better organized chelate building activation. Density functional theory (DFT) was created to properly grasp the optimal architecture of the molecules. The chelates are softer than H2Erx-en, with estimates varying between 95.23 eV to 400.00 eV, compared to 31.47 eV for H2Erx-en. The disc diffusion technique was utilized to assess H2Erx-en and their chelates in an antimicrobial assay against various food and phytopathogens. The zirconium(IV) chelate has the most potent antibacterial action and is particularly efficient against Salmonella typhi. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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12 pages, 1667 KiB  
Article
Thiosemicarbazones and Derived Antimony Complexes: Synthesis, Structural Analysis, and In Vitro Evaluation against Bacterial, Fungal, and Cancer Cells
by Amany Fathy, Ahmed B. M. Ibrahim, S. Abd Elkhalik, Florian Meurer, Michael Bodensteiner and S. M. Abbas
Inorganics 2022, 10(10), 172; https://doi.org/10.3390/inorganics10100172 - 14 Oct 2022
Cited by 7 | Viewed by 1627
Abstract
Two antimony complexes {[Sb(L1)Cl2] C1 and [Sb(L2)Cl2] C2} with the thiosemicarbazone ligands {HL1 = 4-(2,4-dimethylphenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide and HL2 = 4-(2,5-dimethoxyphenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide} were introduced. The structures were elucidated on the basis of a CHNS [...] Read more.
Two antimony complexes {[Sb(L1)Cl2] C1 and [Sb(L2)Cl2] C2} with the thiosemicarbazone ligands {HL1 = 4-(2,4-dimethylphenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide and HL2 = 4-(2,5-dimethoxyphenyl)-1-((pyridin-2-yl)methylene)thiosemicarbazide} were introduced. The structures were elucidated on the basis of a CHNS analysis, spectroscopic techniques (UV-Vis and FT-IR), and DMF solution electrical conductivities. Single crystal X-ray diffraction analysis of complex C1 assigned the complex pseudo-octahedral geometry and triclinic P-1 space group. Only the ligand HL1 and its derived complex C1 displayed antifungal activities against Candida albicans and this activity was enhanced from 10 mm to 21 mm for the respective complex, which is the same activity given by the drug “Amphotericin B”. The ligands HL1 and HL2 gave inhibitions, respectively, of 14 and 10 mm against Staphylococcus aureus and 15 and 10 mm against Escherichia coli; however, complexes C1 and C2 increased these inhibitions to 36 and 32 mm against Staphylococcus aureus and 35 and 31 mm against Escherichia coli exceeding the activities given by the ampicillin standard (i.e., 21 mm against Staphylococcus aureus and 25 mm against Escherichia coli). Against MCF-7 human breast cancer cells, the IC50 values of HL1 (68.9 μM) and HL2 (145.4 μM) were notably enhanced to the values of 34.7 and 37.4 μM for both complexes, respectively. Further, the complexes induced less toxicity in normal BHK cells (HL1 (126.6 μM), HL2 (110.6 μM), C1 (>210.1 μM), and C2 (160.6 μM)). As a comparison, doxorubicin gave an IC50 value of 9.66 μM against MCF-7 cells and 36.42 μM against BHK cells. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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15 pages, 3119 KiB  
Article
Synthesis, Characterization, Computational and Biological Activity of Some Schiff Bases and Their Fe, Cu and Zn Complexes
by Tareq M. A. Al-Shboul, Mohammad El-khateeb, Zaid H. Obeidat, Taher S. Ababneh, Suha S. Al-Tarawneh, Mazhar S. Al Zoubi, Walhan Alshaer, Anas Abu Seni, Taqwa Qasem, Hayato Moriyama, Yukihiro Yoshida, Hiroshi Kitagawa and Taghreed M. A. Jazzazi
Inorganics 2022, 10(8), 112; https://doi.org/10.3390/inorganics10080112 - 2 Aug 2022
Cited by 15 | Viewed by 4108
Abstract
Four new symmetrical Schiff bases derived from 2,2′-diamino-6,6′-dibromo-4,4′-dimethyl-1,1′-biphenyl or 2,2′-diamino-4,4′-dimethyl-1,1′-biphenyl, and 3,5-dichloro- or 5-nitro-salicylaldehyde, were synthesized and reacted with copper-, iron- and zinc-acetate, producing the corresponding complexes. The Schiff bases and their metal complexes were characterized by 1H-, 13C-NMR, IR and [...] Read more.
Four new symmetrical Schiff bases derived from 2,2′-diamino-6,6′-dibromo-4,4′-dimethyl-1,1′-biphenyl or 2,2′-diamino-4,4′-dimethyl-1,1′-biphenyl, and 3,5-dichloro- or 5-nitro-salicylaldehyde, were synthesized and reacted with copper-, iron- and zinc-acetate, producing the corresponding complexes. The Schiff bases and their metal complexes were characterized by 1H-, 13C-NMR, IR and UV-Vis spectroscopy and elemental analysis. The structures of one Schiff base and the two zinc complexes were resolved by X-ray structure determination. Density functional theory (DFT) calculations at the B3LYP/6-31G(d) level of the latter compounds were carried out to optimize and examine their molecular geometries. The biomedical applications of the Schiff bases and their complexes were investigated as anticancer or antimicrobial agents. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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12 pages, 2526 KiB  
Article
Field-Induced Single Molecule Magnetic Behavior of Mononuclear Cobalt(II) Schiff Base Complex Derived from 5-Bromo Vanillin
by Fikre Elemo, Sören Schlittenhardt, Taju Sani, Cyril Rajnák, Wolfgang Linert, Roman Boča, Madhu Thomas and Mario Ruben
Inorganics 2022, 10(8), 105; https://doi.org/10.3390/inorganics10080105 - 25 Jul 2022
Cited by 1 | Viewed by 2347
Abstract
A mononuclear Co(II) complex of a Schiff base ligand derived from 5-Bromo-vanillin and 4-aminoantipyrine, that has a compressed tetragonal bipyramidal geometry and exhibiting field-induced slow magnetic relaxation, has been synthesized and characterized by single crystal X-ray diffraction, elemental analysis and molecular spectroscopy. In [...] Read more.
A mononuclear Co(II) complex of a Schiff base ligand derived from 5-Bromo-vanillin and 4-aminoantipyrine, that has a compressed tetragonal bipyramidal geometry and exhibiting field-induced slow magnetic relaxation, has been synthesized and characterized by single crystal X-ray diffraction, elemental analysis and molecular spectroscopy. In the crystal packing, a hydrogen-bonded dimer structural topology has been observed with two distinct metal centers having slightly different bond parameters. The complex has been further investigated for its magnetic nature on a SQUID magnetometer. The DC magnetic data confirm that the complex behaves as a typical S = 3/2 spin system with a sizable axial zero-field splitting parameter D/hc = 38 cm−1. The AC susceptibility data reveal that the relaxation time for the single-mode relaxation process is τ = 0.16(1) ms at T = 2.0 K and BDC = 0.12 T. Full article
(This article belongs to the Special Issue Synthesis, Structure and Properties of Schiff Base Metal Complexes)
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