Synthesis and characterization of a series of novel metal complexes of N-heterocyclic azo-colorants derived from 4-azo-pyrazol-5-one

Kovalchukova, O. V.; Ryabov, M. A.; Dorovatovskii, Pavel V.; Zubavichus, Yan V.; Утенышев, А. Н.; Kuznetsov, D. N.; Volyansky, Oleg V.; Воронкова, В. К.; Khrustalev, Victor N.

doi:10.1016/j.poly.2016.09.047

Cited by 26 publications

(11 citation statements)

References 35 publications

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“…In all metal complexes, the bond lengths of (C=O) pyr and (C−O) car ranged from (1.208‐1.219 o A) and (1.347‐1.349 o A), respectively, which is shorter than the equivalent values of LFX (1.302 o A) and (1.361 o A), respectively. This variation validates the coordination of pyridon and carboxylic groups via the oxygen atom [56–62] . Table S2 summarizes the total energy, heat of production, and dipole moment of all complexes.…”

Section: Resultssupporting

confidence: 67%

Structural Characterization and Antimicrobial Studies of Some New Mixed Ligand Complexes of Lomefloxacin and 3‐(Bromoacetyl)coumarin with Some Metals

et al. 2022

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The interaction of Mn(II) (1), Fe(II) (2), Co(II) (3), Ni(II) (4), Cu(II) (5), and Zn(II) (6) with lomefloxacin (LFX) in the existence of 3‐(bromoacetyl)coumarin (BAC) and NaOH in a 1 : 1 : 1 : 1 molar ratio resulted in the formation of unique mixed ligand metal complexes. The ability of two ligands to chelate metal ions was investigated by elemental analysis, molar conductance, effective magnetic moments FT‐IR, ultraviolet‐visible (UV‐Vis), 1H NMR spectra and thermogravimetric analyses (TG‐DTG). FT‐IR spectra of the complexes suggest that LFX reacted with metal ions as bi‐dentate through pyridone oxygen and carboxylate oxygen. BAC also interacts as bi‐dentate through oxygen of α,β‐unsaturated ketone and oxygen of lactone carbonyl of coumarin. These chelates are electrolytes, according to conductivity experiments, with a 1 : 1 ratio for Mn(II), Fe(II), and Zn(II) and a 1 : 2 ratio for Co(II), Ni(II), and Cu(II). Electronic and magnetic data revealed an octahedral shape for all compounds. The thermodynamic parameters of thermal breakdown processes such as Ea, ΔH*, ΔS* and ΔG* were determined from TG and DTG curves using Coats‐Redfern (CR) and Horowitz‐Metzeger (HM) techniques for LFX, BAC and their metal complexes. The structural geometry of the complexes is confirmed by molecular modeling studies. The findings show that the complexes are soft with regard to ligands, with values ranging from 0.058 eV for Fe(II) complex to 0.090 eV for Zn(II) complex and 11.11 to 17.24 eV for LFX and BAC, respectively, and 0.121, 8.26 eV and 0.111, 9.009 eV for LFX and BAC. The ligands and their complexes were tested in vitro for antibacterial activity against a variety of bacterial and fungal strains, and the results revealed that the complexes had significantly higher potency than the parent drug.

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Section: Resultssupporting

confidence: 67%

Structural Characterization and Antimicrobial Studies of Some New Mixed Ligand Complexes of Lomefloxacin and 3‐(Bromoacetyl)coumarin with Some Metals

et al. 2022

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“…Also, the angles around M(II) with surrounding oxygen atoms varied from 86.02° to 179.77°; these values not deviated from a regular octahedron. The bond lengths between metal ion and bonded oxygen atoms of NOR (O1 and O5) in all metal complexes varied from (1.925–2.086 Å) and (1.916–2.074 Å), respectively, [ 64–68 ] also, the bond lengths between central metal ion and oxygen atoms of BAC (O6 and O10) are (1.922–2.079 Å) and (1.925–2.075 Å), respectively. [ 69–76 ]…”

Section: Resultsmentioning

confidence: 99%

Study molecular modeling and the effect of some biological metals on the efficiency of norfloxacin in presence of 3‐(bromoacetyl)coumarin

El‐Shwiniy

Gamil

Sadeek

et al. 2021

Applied Organom Chemis

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A series of new mixed ligand metal complexes of Mn(II), Fe(II), Co(II), Ni(II), Cu(II), and Zn(II) have been synthesized by the reaction of norfloxacin (NOR) with 3‐(bromoacetyl)coumarin (BAC) in 1:1:1 (Mn+:NOR:BAC) molar ratio, which characterized by elemental analysis, spectroscopic measurements (FT‐IR, UV–Vis) molar conductance, effective magnetic moments, and thermogravimetric analysis (TG) and (DTG). All the complexes soluble in DMSO and the conductivity measurement indicate that the complexes are electrolyte with ratio 1:1 for Mn(II), Fe(II), and Zn(II) and 1:2 for Co(II), Ni(II), and Cu(II). Electronic and magnetic data elucidated the octahedral structure for all complexes. Assorted thermodynamic factors are calculated, and the results are explicated. Molecular modeling calculations (bond angles, dihedral angles, total energy, heat of formation, and dipole moment) confirm the structural geometry of the complexes and indicate the very good agreement between the computed and experimental geometrical parameters. The calculated data for the hardness (η) and absolute softness (σ) showed that all complexes are soft with respect to ligands. The two ligands and their metal complexes have also been screened for their antibacterial and antifungal activity against some selected species; the data showed that the complexes have remarkable potency as compared with the parent ligands.

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“…The donating centeres N5 and O1 of L are lying trans respect to other nitrogen and oxygen atoms of the other molecule and the two coordinated water molecules. The bond lengths between M‐N5a and M‐N5b of L are shorter than that M‐O1a and M‐O1b of L. [ 57–59 ] Also, the bond angles N5aCON5b is 101.22°, it reflected that the N5a and N5b of the two ligand molecules are lying cis respect to each other. The bond angles O1aCoO1b and O1aCoN5b are 134.00° and 77.99°, it reflects that O1a is trans respect to O1b and cis respect to N5b.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural elucidation, molecular modeling and antimicrobial studies of 6‐(2‐hydroxyphenylimine)‐2‐thioxotetrahydropyrimidin‐4(1H)‐one (L) Schiff base metal complexes

El‐Shwiniy

Ibrahim

Sadeek

et al. 2021

Applied Organom Chemis

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Solid complexes of Schiff base (L) with Co (II), Ni (II), Zn (II), Zr (IV) and Hg (II) in acetone as a solvent were synthesised and characterised by elemental analysis, magnetic measurements, melting point, molar conductivity, FT‐IR, UV–Vis., 1HNMR, X‐ray diffractometer (XRD) and thermogravimetric analyses (TG and DTG). Elemental analysis is in satisfactory correlation with the proposed chemical formulae of the complexes. The estimated molar conductivity of the compounds in 1 × 10−3 M DMF solution indicates the electrolytic existence of the examinated complexes and reported as 1:2 electrolytes for Co (II), Ni (II), Zr (IV) and Hg (II) complexes and 1:1 electrolytes for Zn (II) complex. Spectral and analytical results indicate that L chelated with metal ions as bidenate through the oxygen atom of the carbonyl group and nitrogen atom of azomethine group for all complexes. The XRD patterns demonstrate the non‐crystalline nature (amorphous) of the compounds (1), (4) and (5), but the compounds L, (2) and (3) lie between the amorphous and the crystalline characters. TG/DTG showed the compounds are thermally stable at room temperature and decomposed by raising the temperature to 600°C. The kinetic and thermodynamic parameters such as E*, ΔH*, ΔS* and ΔG* were calculated by using coats‐Redfern and Horowitz‐Metzger methods at n = 1 and n ≠ 1. Calculated values indicate more orderly activated complex formation. The measurements of the molecular modeling using density functional theory (DFT) confirm the structural geometry of the complexes, and the data showed the complexes are soft with respect to L where η varied from 0.068 to 0.077 eV and σ ranges from 12.987 to 14.706 eV, while η and σ for L are 0.109 and 9.174 eV−1, respectively. Complexes were tested for their in vitro antimicrobial activity against certain gram negative and gram positive bacteria in addition to two fungi species. The findings showed a clear increase in the anti‐tuberculosis activity due to complexion.

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Synthesis and characterization of a series of novel metal complexes of N-heterocyclic azo-colorants derived from 4-azo-pyrazol-5-one

Cited by 26 publications

References 35 publications

Structural Characterization and Antimicrobial Studies of Some New Mixed Ligand Complexes of Lomefloxacin and 3‐(Bromoacetyl)coumarin with Some Metals

Structural Characterization and Antimicrobial Studies of Some New Mixed Ligand Complexes of Lomefloxacin and 3‐(Bromoacetyl)coumarin with Some Metals

Study molecular modeling and the effect of some biological metals on the efficiency of norfloxacin in presence of 3‐(bromoacetyl)coumarin

Synthesis, structural elucidation, molecular modeling and antimicrobial studies of 6‐(2‐hydroxyphenylimine)‐2‐thioxotetrahydropyrimidin‐4(1H)‐one (L) Schiff base metal complexes

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