Ni(II), Zn(II), and Fe(III) complexes derived from novel unsymmetrical salen-type ligands: preparation, characterization and some properties

Portakal, Eylem Dilmen; Kaya, Yeliz; Demirayak, Emire; Yeldir, Elif Karacan; Erçağ, Ayşe; Kaya, İsmet

doi:10.1080/00958972.2022.2070485

Cited by 4 publications

(5 citation statements)

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“…Based on the catalytic role of transitional metal complexes in multicomponent reactions, ,,,,,− for the first time in this work, Ni–unsymmetrical salen complexes are utilized as catalysts in a one-pot MCR for the efficient synthesis of ACP derivatives. Multicomponent reactions involving aromatic aldehydes, malononitrile, and dicarbonyl compounds have been carried out under different reaction conditions, with the best results achieved within 1 h at 80 °C under an EtOH solvent medium (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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In this report, four new Ni(II)−unsymmetrical salen complexes, [NiL 1−4 ], were prepared by refluxing Ni(Ac) 2 •4H 2 O with unsymmetrical salen ligands, H 2 L 1−4 . All of the synthesized ligands and complexes were characterized by various physicochemical methods. Also, the solid-state structures of [NiL 1 ], [NiL 2 ], and [NiL 4 ] were defined through single-crystal X-ray diffraction methods. The catalytic potential of [NiL 1−4 ] was investigated by economic and environmentally friendly one-pot-three-component reactions (using reagent: 1,3-dicarbonyls, malononitrile, benzaldehyde, or its derivatives) for the synthesis of biologically active 2amino-3-cyano-4H-pyran derivatives (total 16 derivatives). After optimization of the reaction conditions, this new synthetic protocol by taking Ni(II)−unsymmetrical salen complexes as catalysts shows excellent conversion with a maximum yield of up to 98% of the effective catalytic products within 1 h of reaction time. In addition, it was observed that the aromatic aldehyde containing an electron-withdrawing group as a ring substituent shows better conversion (up to 98%), and the electron-donating group substituent shows similar or less conversion compared to benzaldehyde under the optimized reaction conditions. From the comparison of results between all these Ni complexes, it was found that the efficiency of the catalytic performance follows the order [NiL 1 ] > [NiL 3 ] > [NiL 2 ] > [NiL 4 ]. A possible reaction pathway was predicted and established through UV−vis spectroscopy. Intermediate II proposed in the reaction pathway was also trapped and characterized through 1 H and 13 C NMR.

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Section: Resultsmentioning

confidence: 99%

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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“…The 13 C{H}NMR spectra of all the complexes shows characteristic signals that account for the number of carbon atoms in the respective compounds. The peaks at 165.2, 172.2, 163.9, and 170.9 in the spectra of C1, C2, C3, and C4, respectively, due to the azomethine carbon atoms, affirmed the existence of Schiff base in the complexes (Dilmen et al, 2022).…”

Section: Synthesis and Physico-chemical Characteristics Of The Complexesmentioning

confidence: 86%

“…Similarly, the signal for the azomethine (HC=N) proton in all the complexes appears at 8.88, 9.01, 7.89, and 8.41 ppm in the spectra of C1, C2, C3, and C4, respectively. This signals are expected to appear in the spectra of uncoordinated ligands (Dilmen et al, 2022) around 8.5-8.7 ppm. The shifts to the downfield in C1 and C2, and to the upfield in C3 and C4, are due to the participation of nitrogen atom from the azomethine in the formation of bonding with metal ions through the lone pair of electrons, resulting to M-N bond (Dilmen et al, 2022).…”

Section: Synthesis and Physico-chemical Characteristics Of The Complexesmentioning

confidence: 88%

“…This signals are expected to appear in the spectra of uncoordinated ligands (Dilmen et al, 2022) around 8.5-8.7 ppm. The shifts to the downfield in C1 and C2, and to the upfield in C3 and C4, are due to the participation of nitrogen atom from the azomethine in the formation of bonding with metal ions through the lone pair of electrons, resulting to M-N bond (Dilmen et al, 2022). Aromatic protons were observed in the spectra of C1, C2, C3, and C4 at 7.68-8.14, 6.52-7.91, 6.52-7.26, and 6.43-7.14 ppm, respectively.…”

Section: Synthesis and Physico-chemical Characteristics Of The Complexesmentioning

confidence: 88%

“…The signal for the proton of the hydroxyl (OH) group was completely absent in all the spectra. This signal is expected to be downfield at around 13.00 ppm in the uncoordinated ligand due to the deshielding effect arising from the electronegative oxygen atom (Dilmen Portakal et al, 2022). The disappearance of this signal in all the complexes is due to the deprotonation of the phenolic proton and formation of bond between the metal and oxygen atom of the phenolate group.…”

Section: Synthesis and Physico-chemical Characteristics Of The Complexesmentioning

confidence: 96%

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Template Synthesis of Ni(II) and Zn(II) Complexes Derived from N2O2 Donor Symmetrical Tetradentate Ligands System: Comparative Antioxidant, Xanthine inhibitory, and Computational Studies

Waziri¹

2023

AJBAR

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Four mononuclear symmetric coordination compounds of Ni(II) and Zn(II) (C1–C4), obtained from N2O2 donor Schiff base ligand systems were synthesized in-situ and characterized with a variety of analytical and spectroscopic techniques such as elemental CHN-analysis, 1H-NMR, 13C{H}NMR, UV-Visible, Infrared, powder X-ray diffraction, scanning electron, and high-resolution mass spectroscopies. These analyses revealed that the ligands chelate the metal ions through the oxygen and nitrogen (N2O2) atoms of the phenolate and azomethine functional groups, resulting in distorted and perfect square planar geometry around Zn(II) and Ni(II) ions, respectively. The 2,2-diphenylpicrylhydrazyl (DPPH) radical scavenging and xanthine oxidase activity of the complexes were investigated using in vitro assay techniques. The studies revealed that the complexes possess moderate radical scavenging activity with no or very weak xanthine oxidase activity, in which the controls show better activity than the complexes in both assays. However, C3 and C1 demonstrated some level of activity at higher concentrations but not commensurate with the controls. The DFT calculation of the complexes using the M06- 2X/B3LYP-311G9d.p) level of the theory presented electronic properties that supported the experimental findings on the complexes

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Synthesis, characterization, antioxidant and anticancer activities of a new Schiff base and its M(II) complexes derived from 5-fluorouracil

et al. 2022

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Ni(II), Zn(II), and Fe(III) complexes derived from novel unsymmetrical salen-type ligands: preparation, characterization and some properties

Cited by 4 publications

References 43 publications

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Template Synthesis of Ni(II) and Zn(II) Complexes Derived from N2O2 Donor Symmetrical Tetradentate Ligands System: Comparative Antioxidant, Xanthine inhibitory, and Computational Studies

Synthesis, characterization, antioxidant and anticancer activities of a new Schiff base and its M(II) complexes derived from 5-fluorouracil

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