Crystal engineering of a series of complexes and coordination polymers based on pyrazole-carboxylic acid ligands

Radi, Smaail; Massaoudi, Mohamed El; Benaissa, Houria; Adarsh, N. N.; Ferbinţeanu, Marilena; Devlin, E.; Sanakis, Yiannis; Garcia, Yann

doi:10.1039/c7nj01714f

Cited by 26 publications

(18 citation statements)

References 42 publications

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“…Bipyrazolic ester compounds 1-7 were first synthesized and then converted to their corresponding acid derivatives L1-L7 using a simple hydrolysis reaction in alkaline medium as reported in our previous works [22][23][25][26][27][28]. The structure of these intermediate compounds was checked by spectroscopic and spectrometric methods.…”

Section: Synthesis Of C1-c7mentioning

confidence: 99%

“…Furthermore, bipyrazolic compounds functionalized with two carboxylic groups (Fig. 1) have attracted more attention due to their complexing properties toward metal cations [21][22][23]. In 2008, Chandrasekhar et al reported the synthesis and structure of the first dinuclear triorganotin (IV) [(Ph3Sn)2 (µ-LH) (H2O)] based on bi(pyrazole), obtained from the reaction of (Ph3Sn)2O with 3,5-pyrazoledicarboxylic acid (LH) [24].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, X-ray structure and in vitro antifungal activity of triphenyltin complexes based on pyrazole dicarboxylic acid derivatives

Dahmani

Et-Touhami

Yahyi

et al. 2021

Journal of Molecular Structure

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A series of new ditriphenyltin(IV) dicarboxylate complexes of general formula (Ph3SnOOC-Pz)2R with Pz: pyrazole and R: alkyl or ether, have been synthesized from bipyrazoledicarboxylic acid and hydroxytripheyltin. These complexes, noted C1-C7, have been characterized by IR, 1 H and 13 C NMR spectroscopies. The molecular structures of C3: 1,3-Bis[(5-methyl-2-H-3-triphenyltincarboxylate pyrazol)]propane and C7: Bis[(2-methyl-2H-3triphenyltincarboxylate pyrazol)ethyl]oxide have been confirmed by single crystal X-ray diffraction. Both compounds crystallize in the monoclinic symmetry: C3 in P21 space group with a = 15.915(1) Å, b = 10.0791(8) Å, c = 13.823(1) Å, α = 90°, β = 100.459(3)°, γ = 90° and C7 in P21/n space group, with a = 15.0951(7) Å, b = 8.9847(3) Å, c = 34.244(1) Å, α = 90°, β = 101.421(2)°, γ = 90°.. The two cristallographically independent Sn1 and Sn2 atoms are tetra coordinated within distorted tetrahedral environments, very similar in the two compounds. The antifungal activity of these organotin complexes and their corresponding bipyrazoledicarboxylic acid (ligands) has been evaluated against the pathogenic Fusarium oxysporum f. sp. albedinis. This activity greatly depends on the nature of ligands and on the dose used. The presence of triphenyltin moiety improves considerably the antifungal activity becoming close to that of the benomyl (fungicide).

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Section: Synthesis Of C1-c7mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, X-ray structure and in vitro antifungal activity of triphenyltin complexes based on pyrazole dicarboxylic acid derivatives

Dahmani

Et-Touhami

Yahyi

et al. 2021

Journal of Molecular Structure

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“…For example, we have reported the crystal structures of Co(II)/Cu(II) coordinated complexes of pyrazole-dicarboxylate acid ligand and established their supramolecular structures [16]. In another work, we have demonstrated the effect of the aliphatic backbone of the bis-pyrazole-bis-carboxylate ligand on the supramolecular structures of their Co(II)/Cu(II)/Cd(II) coordination complexes [17]. In a further account, we have studied the effect of anions and hydrogen bonding on the supramolecular structural diversities of Cu(II) and Mn(II) coordination complexes obtained from a novel bis-pyrazole ligand [18].…”

Section: Introductionmentioning

confidence: 94%

New Bis-Pyrazole-Bis-Acetate Based Coordination Complexes: Influence of Counter-Anions and Metal Ions on the Supramolecular Structures

et al. 2020

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A new flexible bis-pyrazol-bis-acetate ligand, diethyl 2,2’-(pyridine-2,6-diylbis (5-methyl-1H-pyrazole-3,1-diyl))diacetate (L), has been synthesised, and three coordination complexes, namely, [Zn(L)2](BF4)2 (1), [MnLCl2] (2) and [CdLCl2] (3) have been obtained. All ligands and complexes were characterised by IR, mass spectroscopy, thermogravimetric analysis and single-crystal X-ray diffraction. Single crystal X-ray diffraction experiment revealed that the primary supramolecular building block of 1 is a hexagonal chair shaped 0D hydrogen bonded synthon (stabilised by C–H∙∙∙O hydrogen bonding and C=O∙∙∙π interactions), which further built into a 2D corrugated sheet-like architecture having a 3-c net honeycomb topology, and finally extended to a 3D hydrogen bonded network structure having a five nodal 1,3,3,3,7-c net, through C–H∙∙∙F interactions. On the other hand, the two crystallographically independent molecules of 2 exhibited two distinct supramolecular structures such as 2D hydrogen bonded sheet structure and 1D zigzag hydrogen bonded chain, sustained by C–H∙O and C–H∙∙∙Cl interactions, which are further self-assembled into a 3,4-c network structure, and 3 showed a 2D hydrogen bonded sheet structure. The supramolecular structural diversity in these complexes is due to the different conformations adopted by the ligands, which are mainly induced by different metal ions with coordination environments controlled by different anions. Hirshfeld surface analysis was explored for the qualitative and quantitative analysis of the supramolecular interactions.

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“…Carboxy-substituted pyrazoles were used for the construction of highly porous metal-organic frameworks [ 18 , 19 , 20 , 21 ]. Carboxylic acids based on bis(pyrazol-1-yl)alkanes are much less explored and only a few research papers were published so far [ 22 , 23 , 24 , 25 ]. In addition, a series of works devoted to the synthesis of metal-organic frameworks based on structurally related bis(4-carboxyphenylpyrazol-1-yl)methane was carried out by Sumby et al, the presence of the free chelating units in the structure of the framework allowed them to prepare catalysts with single metal sites [ 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Approaches to the Synthesis of Dicarboxylic Derivatives of Bis(pyrazol-1-yl)alkanes

Burlutskiy

Potapov

2021

Molecules

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Carboxylation of bis(pyrazol-1-yl)alkanes by oxalyl chloride was studied. It was found that 4,4′-dicarboxylic derivatives of substrates with electron-donating methyl groups and short linkers (from one to three methylene groups) can be prepared using this method. Longer linkers lead to significantly lower product yields, which is probably due to instability of the intermediate acid chlorides that are initially formed in the reaction with oxalyl chloride. Thus, bis(pyrazol-1-yl)methane gave only monocarboxylic derivative even with a large excess of oxalyl chloride and prolonged reaction duration. An alternative approach involves the reaction of ethyl 4-pyrazolecarboxylates with dibromoalkanes in a superbasic medium (potassium hydroxide–dimethyl sulfoxide) and is suitable for the preparation of bis(4-carboxypyrazol-1-yl)alkanes with both short and long linkers independent of substitution in positions 3 and 5 of pyrazole rings. The obtained dicarboxylic acids are interesting as potential building blocks for metal-organic frameworks.

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Crystal engineering of a series of complexes and coordination polymers based on pyrazole-carboxylic acid ligands

Abstract: Three new complexes and two coordination polymers have been synthesized.

Cited by 26 publications

References 42 publications

Synthesis, characterization, X-ray structure and in vitro antifungal activity of triphenyltin complexes based on pyrazole dicarboxylic acid derivatives

Synthesis, characterization, X-ray structure and in vitro antifungal activity of triphenyltin complexes based on pyrazole dicarboxylic acid derivatives

New Bis-Pyrazole-Bis-Acetate Based Coordination Complexes: Influence of Counter-Anions and Metal Ions on the Supramolecular Structures

Approaches to the Synthesis of Dicarboxylic Derivatives of Bis(pyrazol-1-yl)alkanes

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