Lipophilic N-[2-hydroxyimino-2-(pyridin-2-yl)ethyl]trialkylammonium salts - New ligands for metal ion extractions into organic solvents

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6849-6852

  Cibulka, Radek ^a   Hampl, František ^a   Šmidrkal Jr , Jan ^a   Liška, František ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Complexes; Liquid membrane; Oximes; Pyridines

Indexed keywords

AMMONIUM CHLORIDE; HYDROXYLAMINE; METAL ION; NICKEL; ORGANIC SOLVENT; OXIME; PYRIDINE DERIVATIVE; SURFACTANT;

AQUEOUS SOLUTION; ARTICLE; CHELATION; CHEMICAL STRUCTURE; EXTRACTION; ION TRANSPORT; LIQUID MEMBRANE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033543615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01382-9     Document Type: Article

References (17)

1. Moyer, B. A.: in Comprehensive Supramolecular Chemistry, Vol. I (Atwood, J. B., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.), 377-413; Elsevier Science, Ltd., Oxford, 1996 and references cited therein;
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3. c) Rydberg, J., Musikas, C., Choppin, G. R., Eds.: Principles and Practices of Solvent Extraction. Dekker, New York, 1992;
4. d) Noble, R. D., Way, J. D.: in Liquid Membranes, Theory and Applications (Noble, R. D., Way, J. D., Eds.), 1-27 and 110-122, ACS; Washington DC, 1987;
5. e) Araki, T., Tsukube, H., Eds.: Liquid Membranes: Chemical Applications; CRC Press, Boca Raton, 1990;
6. f) Cecille, L., Casarci, M., Pietrelli, L., Eds.: New Separation Chemistry Techniques for Radioactive Waste and Other Specific Applications; Elsevier Applied Science, Amsterdam, 1991 and references cited therein.
7. Cibulka, R., Dvořák, D., Hampl, F., Liška, F.: Collect. Czech. Chem. Commun. 1997, 62, 1342-1354.
8. 2; 7.49 ddd, 1H, J(5′,4′) = 7.3, J(5′,6′) = 5.0, J(5′3′) = 1.6, (H-5′); 7.91 ddd, 1H, J(4′,3′) = J(4′,5′) = 7.6, J(4′,6′) = 1.6, (H-4′); 7.97 d, 1H, J(3′,4′) = 7.6, (H-3′); 8.13 dd, 2H, J(3,2) = J(3,4) = J(5,4) = = J(5,6) = 6.9, (H-3, H-5); 8.59 t, 1H, J(4,3) = J(4,5) = 8.2 (H-4); 8.64 d, 1H, J(6′,5′) = 4.9, (H-6′); 9.13 d, 2H, J(2,3) = J(6,5) = 6.8, (H-2, H-6);
9. 2C=); 7.50 dd, 1H, J(5,4) = 7.3; J(5,3) = 5.2, (H-5); 7.95 m, 2H, (H-3, H-4); 8.63 d, 1H, J(6,5) = 4.4, (H-6);
10. 2C=); 7.28 m, 1H, (H-5); 7.70 ddd, 1H, J(4,3) = J(4,5) = 7.8, J(4,6) = = 1.7, (H-4); 8.11 d, 1H, J(3,4) = 8.1, (H-3); 8.50 d, 1H, J(6,5) = 4.6, (H-6).
11. Wimalasena, K., Haines, D. C.: J. Org. Chem. 1994, 6472-6475, 59.
12. 6, we expected 1 : 2 metal : ligand stoichiometry.
13. Hampl, F., Liška, F., Mancin, F., Tecilla, P., Tonellato, U.: Langmuir 1999, 15, 405.
14. 2+) was added to this solution and stirred at 60 °C for 3 h. The solid was filtered off and washed with 50% aqueous ethanol. The filtrate was extracted with chloroform, the extract dried with sodium sulfate and the solvent was evaporated. The crude product was dissolved in methanol and then treated with Amberlite IRA 400 (OH), neutralized with nitric acid, evaporated and crystallized from ethyl acetate (single-chained salts 1a-c) or petroleum ether (double-chained salts 1d,e).
15. A glass tube (48 mm and 44.5 mm were the external and the internal diameters, respectively) was immersed coaxially into a cylindrical glass vessel (internal diameter 57 mm) beneath the surface of the chloroform layer (70 ml), thus separating two aqueous phases: the source phase (50 ml) and the receiving phase (25 ml). The chloroform layer (liquid membrane) was stirred slowly by a mechanical stirrer keeping the phase interfaces motionless.
16. a) Menger, F., Jeng-Jong, L.: J. Org. Chem. 1993, 58, 1909-1916;
17. b) Pflaum, R. T., Wehking, M. W., Jensen, R. E.: Talanta 1964, 11, 1193-1196.