ChemInform Abstract: A Novel Macrocyclic Ligand Containing 2,6‐Bis(pyrazol‐5‐yl)pyridine Units.

Gál, Melinda; Tarrago, G.; Steel, P. J.; Marzin, C.

doi:10.1002/chin.198608218

Cited by 3 publications

(4 citation statements)

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“…The literature reports several pyrazole-containing macrocycles (6,14,15). Of special interest to us were a bicyclic cryptand from a 3 + 2 alkylation of ammonia with a doubly electrophilic 2,2'-bipyrazole (15) and a macromonocycle obtained by 2 + 2 alkylation of 2,6-bis(5-methylpyrazol-3-y1)pyridine with bis(chloromethy1) ether (6). However, this latter reaction proceeded in only 2% yield and was accompanied by more substantial amounts of the 1 + 1 product.…”

Section: : X -C Hmentioning

confidence: 99%

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Short syntheses of rigid acyclic or macrocyclic poly-imine ligands and their use in Ru(II), Fe(III), and alkali metal complexation

Dash¹,

Potvin²

1992

Can. J. Chem.

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ROBERT DASH and PIERRE G. POTVIN. Can. J. Chem. 70, 2249 (1992. Lipophilic derivatives of 2,6-bis(3-pyrazoly1)pyridine and 1,3-bis (3-pyrazoly1)benzene were obtained in acceptable yields by Stork reactions and transformed by N-alkylations into three pentadentates, three bis(bidentates), and one macrocyclic octadentate ligand. The parent bis(pyrazoly1) pyridine constituted a terpyridine analogue and readily formed a Ru(I1) complex. By comparison of 'H nuclear magnetic resonance patterns, it was found that the alkylations in the bis(pyrazoly1)pyridine series conferred an anti,anti conformation of the imino nitrogens. The pentadentates were then able to extract alkali metal ions into CHCI, with only modest strength and selectivity, but the preferred extraction of Li' by one of these was notable. By variation of the reaction conditions, a tri-iron(II1) and a di-iron(II1) complex were obtained from a bis(bidentate).ROBERT DASH et PIERRE G. POTVIN. Can. J. Chem. 70, 2249Chem. 70, (1992. Des derives lipophiles de la 2,6-bis(3-pyrazo1yle)pyridine et du 1,3-bis(3-pyrazoly1e)benzkne furent prepares en rendements acceptables par des reactions de Stork, puis N-alkylks pour fournir trois pentadentates, trois bis(bidentate) et un octadentate macrocyclique. En tant qu'analogue de la terpyridine, la bis(pyrazolyle)pyridine forma aisement un complexe au Ru(I1). D'aprks la resonance magnetique nuclkaire, les alkylations de la bis(pyrazoly1e)pyridine ont force l'adoption de conformations anti,anti et les pentadentates etaient donc de modestes recepteurs pour les cations alkalins et ont demontrk une faible sClectivit6 en extraction dans le chloroforme. Neanmoins, on souligne l'extraction preferentielle du Li' par l'un d'eux. Un bis(bidentate1 forma, selon les conditions employees, des complexes bi-et tri-nuclkaires avec le Fe(II1).

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Section: : X -C Hmentioning

confidence: 99%

“…Purification was carried out by column chromatography on alumina using 2 : 98 MeOH : CH2CI2 as eluent. The pyrazole was recrystallized from EtOH (1.08 g, 64% yield), mp 123-125°C; 'H nrnr (CDC1,) 6 (20), 49 (20). Anal.…”

Section: Ih-3-phenyl-4567-tetrahydrobenzopyrazole Imentioning

confidence: 99%

Short syntheses of rigid acyclic or macrocyclic poly-imine ligands and their use in Ru(II), Fe(III), and alkali metal complexation

Dash¹,

Potvin²

1992

Can. J. Chem.

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“…Following the approach of slightly modifying the BTP skeleton, we synthesized 2,6-bis(5-(2,2-dimethylpropyl)-1 H -pyrazol-3-yl)pyridine (C5-BPP; Scheme ). − The structure of C5-BPP can be viewed as intermediate between the BTPs and 6-(3,5-dimethyl-1 H -pyrazol-1-yl)-2,2′-bipyridine (dmpbipy), a ligand with weak complexing power for the trivalent actinides studied earlier …”

Section: Introductionmentioning

confidence: 99%

2,6-Bis(5-(2,2-dimethylpropyl)-1H-pyrazol-3-yl)pyridine as a Ligand for Efficient Actinide(III)/Lanthanide(III) Separation

et al. 2012

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The N-donor complexing ligand 2,6-bis(5-(2,2-dimethylpropyl)-1H-pyrazol-3-yl)pyridine (C5-BPP) was synthesized and screened as an extracting agent selective for trivalent actinide cations over lanthanides. C5-BPP extracts Am(III) from up to 1 mol/L HNO(3) with a separation factor over Eu(III) of approximately 100. Due to its good performance as an extracting agent, the complexation of trivalent actinides and lanthanides with C5-BPP was studied. The solid-state compounds [Ln(C5-BPP)(NO(3))(3)(DMF)] (Ln = Sm(III), Eu(III)) were synthesized, fully characterized, and compared to the solution structure of the Am(III) 1:1 complex [Am(C5-BPP)(NO(3))(3)]. The high stability constant of log β(3) = 14.8 ± 0.4 determined for the Cm(III) 1:3 complex is in line with C5-BPP's high distribution ratios for Am(III) observed in extraction experiments.

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“…More recently, the synthesis of two macrocyclic tetrapyrazolic compounds was reported 3. Such structures are expected to form stable complexes both with transition and alkali metals 4–11. In fact, liquid–liquid extraction experiments carried out with the compounds represented in Figure 1 were successful with both series of metal ions 3.…”

Section: Introductionmentioning

confidence: 98%

Extraction of metal ions from water with tetrapyrazolic macrocycles bound to Merrifield resin and silica gel

Radi

Ramdani

Lekchiri

et al. 2000

J. Appl. Polym. Sci.

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Two macrocyclic tetrapyrazolic compounds having internal cavities of different sizes of were covalently bound both to a porous silica gel and to a Merrifield resin. The ability of these sorbents to extract heavy and akali metal ion from water by a solid–liquid extraction process was studied and compared to results of classical liquid–liquid extraction with the unbound pyrazole compounds. The grafting at the surface of silica does not affect the complexing properties of the ligands. However, the hydrophobic nature of the Merrifield resin has a marked effect, especially on the selectivity of extraction between the alkali metals. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 2495–2499, 2000

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ChemInform Abstract: A Novel Macrocyclic Ligand Containing 2,6‐Bis(pyrazol‐5‐yl)pyridine Units.

Abstract: Das aus Pyridin‐2,6‐dicarbonsäurediethylester, Methylketonen und Hydrazin zugängliche Bis‐pyrazolylpyridin (I) reagiert mit Bis(chlormethyl)‐ether unter Phasen‐Transfer‐Katalyse zu einem Gemisch der Makrocyclen (II) und (III).

Cited by 3 publications

References 0 publications

Short syntheses of rigid acyclic or macrocyclic poly-imine ligands and their use in Ru(II), Fe(III), and alkali metal complexation

Short syntheses of rigid acyclic or macrocyclic poly-imine ligands and their use in Ru(II), Fe(III), and alkali metal complexation

2,6-Bis(5-(2,2-dimethylpropyl)-1H-pyrazol-3-yl)pyridine as a Ligand for Efficient Actinide(III)/Lanthanide(III) Separation

Extraction of metal ions from water with tetrapyrazolic macrocycles bound to Merrifield resin and silica gel

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