2,2′-Dipyridyl-6,6′-dicarboxylic acid diamides: Synthesis, complexation and extraction properties

Alyapyshev, M. Yu.; Бабаин, В. А.; Borisova, Nataliya E.; Eliseev, I. I.; Kirsanov, Dmitry; Kostin, Andrey; Legin, Andrey; Reshetova, M. D.; Smirnova, Z. I.

doi:10.1016/j.poly.2010.03.021

Cited by 62 publications

(23 citation statements)

References 24 publications

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“…When comparing these results with the data on potentiometric sensors based on 2,2'-dipyridyl-6,6-dicarboxylic acid diamides 6,7 and dipicolinamide 41,42 one can see that less rigid dipyridyldiamide and dipicolindiamide structures allow for more selective cadmium and lead sensors, correspondingly. No sensitivity to cobalt and nickel was found.…”

Section: Sensorsmentioning

confidence: 82%

1,10-Phenanthroline-2,9-dicarboxamides as ligands for separation and sensing of hazardous metals

et al. 2016

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1,10-phenanthroline-2,9-dicarboxamides of various structure were synthesized and studied as ligands for separation and sensing of d-and f-metals. It was found that the extraction ability of dialkyl-diaryl-diamide to lanthanides decreases from La to Lu and extraction of Am is close to light lanthanides (La-Pr). Tetraalkyl-diamide are not selective to lanthanides, instead exhibiting moderate selectivity in Am/Ln separation. The diamide complexes with lanthanides and d-elements were synthesized and characterized by XRD analysis. All diamides have demonstrated good extraction ability to environmentally hazardous metals (cadmium, lead, copper). The synthesized compounds were also tested as ionophores in PVC-plasticized potentiometric sensor membranes. Such sensors displayed no perceptible response to lanthanides but exhibited high sensitivity towards copper, zinc, cadmium and lead. These compositions can be considered as promising cross-sensitive sensors for multisensor systems.

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Section: Sensorsmentioning

confidence: 82%

1,10-Phenanthroline-2,9-dicarboxamides as ligands for separation and sensing of hazardous metals

et al. 2016

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“…The 4,4’‐dinitro and 4,4’‐dibrom‐2,2’‐bipyridine‐6,6’‐dicarboxylic acids 2 were prepared by the oxidation of corresponding 4,4’‐substituted 6,6’‐dimethyl‐2,2’‐bipyridines which were synthesized according to the following scheme (Scheme ). Chromium oxide oxidation were previously used for 2,2‐bipyridine‐6,6’‐dicarboxylic acid preparation ,. Bis‐N‐oxide of 6,6’‐dimethyl‐2,2’‐bipyridine was nitrated to provide 4,4’‐dinitro‐6,6’‐dimethyl‐2,2’‐bipyridine; after that the 4,4’‐dibromo‐6,6’‐dimethyl‐2,2’‐bipyridine was prepared in high yield by a method modified from the original work of Mukkala and Kankare .…”

Section: Resultsmentioning

confidence: 99%

“…However, the separation of americium by diamides of 2,2’‐bipyridine‐6,6’‐dicarboxylic acid follows the same trends as CMPO molecules. Introducing the aromatic ring into the amidic moiety shows sharp increases in metal distribution coefficients, and the subsequent substitution of the aromatic ring with alkyl groups also improves the extraction ,. The distribution coefficients demonstrate a tenfold rise when going from N ‐ethylanilide to N‐ethyl‐ p‐ alkylanilides of 2,2’‐bipyridine‐6,6’‐dicarboxylic acid .…”

Section: Introductionmentioning

confidence: 99%

Screening of the Structure of Americium Extractants Based on a 2,2’‐Bipyridyl Scaffold: a Simple Way to a N2,O2‐Tetradentate Ligands Library for Rational Design of An/Ln Extractants

et al. 2018

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A library of N-ethylanilides of 2,2'-bipyridine-6,6'-dicarboxylic acids were synthesized to evaluate the influence of the side chains on the extraction properties. The structure of the various diamides is studied in solid state by X-ray and in solution by 2D NMR. In the solid-state, the diamides featured flat Cs geometry irrespective of the nature and position of the substituents. Carboxylic groups in the crystals shifted from the residing planes of both pyridine and aromatic anilide rings indicating disruption of the conjugated system. The solution behaviour is substituent dependent. Only three types of relative orientations of amidic fragments and pyridine rings were found in solutions of diamides depending on the nature of the amidic side chain substituents. The conformations of the diamides mostly depended on the size of the substituent and less on their electronic properties. Solubility of the diamides and their metal extraction properties in relation to americium and europium ions were studied the diamides, bearing substituents in pyridine rings and in phenyl ring of diamide moiety (one or two alkyl-, alkoxy-, fluorine-, carboxylic-groups). The symmetrical substitution in the pyridine moiety critically diminished both solubility and metal extraction. Metal ions recovery strongly depended on the substitution in the anilidic moiety; distribution coefficients depended more on the spatial arrangement of the substituents and to a lesser extent on their electronic properties.[a] Dr.

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“…However, the extraction ability measured for molecules possessing as alkyl as aryl substituents is higher than for ligands, substituted only with alkyl fragments. Effect of the “anomalous aryl strengthening” was observed for different ligands: for bidentate organophosphorus compounds, carbamoylphosphineoxides, and diamides of heterocyclic dicarboxylic acids …”

Section: Introductionmentioning

confidence: 99%

Complexes of Uranyl Nitrate with 2,6-Pyridinedicarboxamides: Synthesis, Crystal Structure, and DFT Study

Alyapyshev

Бабаин

Ткаченко

et al. 2017

Z. Anorg. Allg. Chem.

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2,2′-Dipyridyl-6,6′-dicarboxylic acid diamides: Synthesis, complexation and extraction properties

Cited by 62 publications

References 24 publications

1,10-Phenanthroline-2,9-dicarboxamides as ligands for separation and sensing of hazardous metals

1,10-Phenanthroline-2,9-dicarboxamides as ligands for separation and sensing of hazardous metals

Screening of the Structure of Americium Extractants Based on a 2,2’‐Bipyridyl Scaffold: a Simple Way to a N2,O2‐Tetradentate Ligands Library for Rational Design of An/Ln Extractants

Complexes of Uranyl Nitrate with 2,6-Pyridinedicarboxamides: Synthesis, Crystal Structure, and DFT Study

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