New functionalised C,C-bipyrazoles. Synthesis and cation binding properties

Attayibat, Ahmed; Radi, Smaail; Lekchiri, Yahya; Ramdani, Abdelkrim; Hacht, Brahim; Morcellet, Michel; Bacquet, Maryse; Willai, Stephanie

doi:10.3184/030823406779173587

Cited by 18 publications

(17 citation statements)

References 23 publications

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“…[10][11][12][13][14][15][16][17][18] However, the present ligands 5-7 towards others metals. We can thus suggest an important selectivity for these ligands towards copper and lead.…”

Section: Liquid-liquid Extraction Of Individual Cationsmentioning

confidence: 94%

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New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

Radi

Attayibat

Ramdani

et al. 2009

Journal of Chemical Research

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The synthesis of two new C,C-pyridylpyrazole isomers with a functionalised arm is described. The complexation capabilities of these ligands compared to their homologues towards bivalent metals (Hg 2+ , Cd 2+ , Pb 2+ , Cu 2+ , Zn 2+ ) and alkali metal ions (K + , Na + , Li + ) were investigated using a liquid-liquid extraction process. The percentage limits of extraction were determined by atomic absorption measurements.Chelating ligands based on the pyrazole ring have been described extensively in the literature 1-6 including several reviews. 7-9 In our recent work, a series of acyclic pyrazole compounds containing one, two, three or four pyrazole rings were prepared and demonstrated to extract only transition metal cations, 10-15 whereas macrocyclic pyrazolic compounds are expected to also form stable complexes with alkali metals. [16][17][18] This aptitude is mainly due to the presence of sp 2 hybrid nitrogen donors with the involvement of geometry and the nature of the ligands.Pyrazole-associated pyridine groups showed also the ability to complex transition metal ions. [19][20][21][22][23][24] However, complexation studies of pyridylpyrazole compounds are less well-known in the literature. It was therefore interesting to increase the diversity of pyridylpyrazole-based ligands with a view to study their complexation capabilities compared to ligands with pyrazoles units only.Here, we report the synthesis of two new C,C-pyridylpyrazole isomers 5 and 6 ( Fig. 1) with a donor heteroatom in a side chain. The complexation capabilities of these new functionalised C,C-pyridylpyrazole isomers 5 and 6 compared to their homologues such as unfunctionalised C,C-pyridylpyrazole 7, 23 C,N-pyridylpyrazole 8 24 and pyrazolylpyrazole 9 11 ligands were investigated using a liquid-liquid extraction process towards bivalent metal ions (Hg 2+ , Cd 2+ , Pb 2+ , Cu 2+ , Zn 2+ ) and alkaline metal ions (Li + , Na + , K + ). The relative capabilities of theses receptors in extracting theses cations were determined by the measurement of extracted cation percentage by atomic absorption.

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“…[10][11][12][13][14][15][16][17][18] However, the present ligands 5-7 towards others metals. We can thus suggest an important selectivity for these ligands towards copper and lead.…”

Section: Liquid-liquid Extraction Of Individual Cationsmentioning

confidence: 94%

“…Structures of synthesised C,C-pyridylpyrazole isomers 5 and 6 and literature ligands 7, 23 8 24 and 9 11. …”

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confidence: 99%

New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

Radi

Attayibat

Ramdani

et al. 2009

Journal of Chemical Research

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“…Many pyrazole derivatives have been reported to possess antimicrobal, antiinflammatory, analgesic, anticancer activities as well as the fungicidal and pesticidal activities [3,4]. In addition, due to significant complexation abilities, pyrazole based ligands found applications as extraction reagents for metal ions [5]. Different pyrazole based ligands are used in the synthesis of complexes with the pronounced magnetic properties and also as building blocks of metal organic frameworks [6].…”

Section: Commentmentioning

confidence: 99%

Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C₉H₇BrN₂O

Jaćimović

Kosović

Novaković

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Product P3 was prepared, as previously described [22,23], from 3(5)-amino-5(3)-methylpyrazole P2 by diazotation in HCl followed by reduction with tin chloride and condensation with betadiketones. Finally, the methylation of the precursor in the presence of t-BuOK as base led to one isolated isomer of P3 in good yield.…”

Section: Synthesis Of the Pyrazole Compoundsmentioning

confidence: 99%

The effect of 1′,3,5,5′-tetramethyl-1′H-1,3′-bipyrazole on the corrosion of steel in 1.0 M hydrochloric acid

et al. 2011

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The effect of some prepared compounds, namely 3,5-dimethyl-1H-pyrazole (P1), 3(5)-amino-5(3)-methylpyrazole (P2), and 1 0 ,3,5,5 0 -tetramethyl-1 0 H-1,3 0 -bipyrazole (P3), on the corrosion behaviour of steel in 1.0 M hydrochloric acid solution as corrosive medium has been investigated at 308 K using weight-loss measurement, potentiodynamic polarisation, linear polarisation, and impedance spectroscopy (EIS). Generally, inhibition efficiency of the investigated compounds was found to depend on the concentration and nature of the inhibitor. P3 was a better inhibitor than P1 and P2, and its inhibition efficiency increased with increasing concentration of inhibitor, attaining 94% above 10 -3 M. Potentiodynamic polarisation studies clearly reveal that P3 acts essentially as a cathodic inhibitor. E (%) values obtained from different methods are in reasonably good agreement. EIS measurements show an increase of transfer resistance with inhibitor concentration. Partial p-charge on atoms was calculated. Correlation between the highest occupied molecular orbital energy E HOMO and inhibition efficiencies was sought. The temperature effect on the corrosion behaviour of steel in 1.0 M HCl without and with different concentrations of inhibitor P3 was studied in the temperature range 308 to 343 K. Thermodynamic data, for example heat of adsorption (DH ads ), entropy of adsorption (DS ads ) and free energy of adsorption (DG ads ) were calculated by use of thermodynamic equations. Kinetic activation data, for example E a , DH*, DS* and pre-exponential factor, were calculated, and are discussed. The inhibiting action of P3 on the corrosion of steel in 1-10 M hydrochloric acid was also studied by weight-loss measurement. The rate constant and reaction constant were calculated for the corrosion reactions. Adsorption of P3 on the steel surface in 1.0 M HCl follows the Langmuir isotherm model.

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New functionalised C,C-bipyrazoles. Synthesis and cation binding properties

Cited by 18 publications

References 23 publications

New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C₉H₇BrN₂O

The effect of 1′,3,5,5′-tetramethyl-1′H-1,3′-bipyrazole on the corrosion of steel in 1.0 M hydrochloric acid

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New functionalised C,C-bipyrazoles. Synthesis and cation binding properties

Cited by 18 publications

References 23 publications

New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

New Functionalised C,C-pyridylpyrazoles: Synthesis and Cation Binding Properties

Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O

The effect of 1′,3,5,5′-tetramethyl-1′H-1,3′-bipyrazole on the corrosion of steel in 1.0 M hydrochloric acid

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Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C₉H₇BrN₂O