Metallomicelles Made of Ni(II) Complexes of Lipophilic 2-Pyridineketoximes as Powerful Catalysts of the Cleavage of Carboxylic Acid Esters

Langmuir

Volumn 15, Issue 2, 1999, Pages 405-412

  Hampl, Frantisek ^a   Liska, Frantisek ^a   Mancin, Fabrizio ^b   Tecilla, Paolo ^b   Tonellato, Umberto ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSTS; COBALT COMPOUNDS; COPPER COMPOUNDS; ESTERS; HYDROLYSIS; NICKEL COMPOUNDS; NITROGEN COMPOUNDS; ORGANOMETALLICS; PH EFFECTS; STOICHIOMETRY; ZINC COMPOUNDS;

DIPHENYLPHOSPHORIC ACID; PYRIDINEKETOXIMES;

MICELLES;

EID: 0032804170     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la980861+     Document Type: Article

References (45)

1. (a) Gellman, S. H.; Petter, R.; Breslow, R. J. Am. Chem. Soc. 1986, 108, 2388.
2. (b) Menger, F. M.; Can, L. H.; Johnson, E.; Durst, D. H. J. Am. Chem. Soc. 1987, 109, 2800.
3. (c) Fornasier, R.; Scrimin, P.; Tecilla, P.; Tonellato, U. J. Am. Chem. Soc. 1989, 111, 224.
4. (d) Weijnen, J. G. J.; Koudijs, A.; Engbersen, J. F. J J. Org. Chem. 1992, 57, 7258.
5. (e) Ogino, K.; Kashihara, N.; Ueda, T.; Isaka, T.; Yoshida, T.; Tagaki, W. Bull. Chem. Soc. Jpn. 1992, 65, 373.
6. (f) Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1991, 56, 161.
7. (g) Scrimin, P.; Tecilla, P.; Tonellato, U. J. Am. Chem. Soc. 1992, 114, 5086.
8. (h)Scrimin, P.; Tecilla, P.; Tonellato, U. J. Org. Chem. 1994, 59, 18.
9. (i) Bunton, C. A.; Scrimin, P.; Tecilla, P. J. Chem. Soc., Perkin Trans. 2 1996, 419.
10. (j) Krisle, A. G.; Vizitiu, D.; Thatcher, R. J. Chem. Commun. 1996, 913.
11. (k) Scrimin, P.; Tecilla, P.; Moss, R. A.; Bracken, K. J. Am. Chem. Soc. 1998, 120, 1179.
12. (a) Bedford, C. D.; Harris, R. W.; Howd, R. A.; Miller, A.; Nolen, H. W., III; Kenley, R. A. J. Med. Chem. 1984, 27, 1431.
13. (b) Kenley, R. A.; Bedford, C. D.; Dailey, O. D.; Howd, R. A.; Miller, A. J. Med. Chem. 1984, 27, 1201.
14. (c) Bedford, C. D.; Miura, M.; Bottaro, J. C.; Howd, R. A.; Nolen, H. W., III. J. Med. Chem. 1986, 29, 1689.
15. Terrier, F.; MacCormack, P.; Kizilian, E.; Hallè, J.-C.; Demergeman, P.; Guir, F.; Lion, C. J. Chem. Soc., Perkin Trans. 21991, 153 and references cited therein.
16. (a) Orama, M.; Saarinen, H.; Korvenranta, J. Acta Chem. Scand. 1989, 43, 407.
17. (b) Suh, J.; Cheong, M.; Suh, M. P. J. Am. Chem. Soc. 1982, 104, 1645.
18. (c) Breslow, R.; Chipman, D. J. Am. Chem. Soc. 1965, 87, 4195.
19. (d) Suh, J.; Suh, M. P.; Lee, J. D. Inorg. Chem. 1985, 24, 3088.
20. (e) Suh, J.; Cheong, M.; Han, H. Bioorg. Chem. 1984, 12, 188.
21. (a) Fendler, J. Membrane Mimetic Chemistry; Wiley: New York, 1982.
22. (b) Fendler, J. H.; Fendler, J. E. Catalysis in Micellar and Macromolecular Systems; Academic Press: New York, 1975.
23. (c) Bunton, C. A.; Savelli, G. Adv. Phys. Org. Chem. 1986, 22, 213.
24. (d) Fornasier, R.; Tonellato, U. J. Chem. Soc., Faraday Trans. 1980, 76, 1301.
25. (e) Bunton, C. A.; Nome, F.; Quina, F. H.; Romsted, L. Acc. Chem. Res. 1991, 24, 357.
26. (f) Menger, F. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1088.
27. Budka, J.; Hampl, F.; Liska, F.; Scrimin, P.; Tecilla, P.; Tonellato, V. J. Mol. Catal., A 1996, 104 (3), 201.
28. A similar slow complexation of Ni(II) by lipophilic 2-pyridine aldoxime comicellized with CTABr has already been described: Hebrant, M.; Bouraine, A.; Tondre, C.; Brembilla, A.; Lochen, P. Langmuir 1994, 10, 3994.
29. Riggle, K.; Lynde-Kernell, T.; Schlemper, E. O. J. Coord. Chem. 1992, 25, 117.
30. b which follow the same trend.
31. Suh, J.; Cheong, M.; Han, H. Bioorg. Chem. 1984, 12, 188.
32. (a) Suh, J. Bioorg, Chem. 1990, 18, 345.
33. (h) Suh, J. Acc. Chem. Res. 1992, 25, 274 and references therein.
34. Suh, J.; Chang, B. Bioorg. Chem. 1987, 15, 167.
35. A decrease of the formation constant by dissolving the ligand in cationic micelles is expected: Scrimin, P.; Tecilla, P.; Tonellato, U.; Vendrame, T. J. Org. Chem. 1989, 64, 5988.
36. Cibulka, R.; Dvorak, D.; Hampl, F.; Liska, F. Collect. Czech. Chem. Commun. 1997, 62, 1342.
37. (a) Epstein, J.; Kaminski, J., J.; Bodor, N.; Enever, R.; Sowa, J.; Higuchi, T. J. Org. Chem. 1978, 43, 2816.
38. (b) Reiner, R.; Rossman, K. Monatsh, Chem. 1982, 113, 223.
39. (c) Lion, C.; Despapie, B.; Delmas, G.; Fosset, L. Bull. Soc. Chim. Belg. 1991, 700, 549.
40. (d) Hampl, F.; Mazac, J.; Liska, F.; Srogl, J.; Kabrt, L.; Suchanek, M. Collect. Czech. Chem. Commun. 1995, 60, 883.
41. Holzbecher, Z. Handbook of Organic Reagents in Inorganic Analysis; Wiley: Chicheater, 1976.
42. Gulick, W. M., Jr.; Geske, D. H. J. Am. Chem. Soc. 1966, 88, 2928.
43. Blanch, J. H.; Onsanger, O. T. J. Chem. Soc. 1965, 3737.
44. Menassè, R.; Klein, G.; Erlenmeyer, H. Helv. Chim. Acta 1966, 38, 1289.
45. The fit of the data was made using the software package Enzfuter: Leatherbarrow, R. J. Enzfitter, Elsevier: Amsterdam, 1987.