Polymerization- and solvent-triggered cooperativity between copper(II) ions in the catalysis of the hydrolysis of amino esters by pyridine-based ligands

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1143-1153

  Scrimin, Paolo ^a   Tecilla, Paolo ^a   Tonellato, Umberto ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

Amino esters hydrolysis; Cooperativity; Copper(II) ions; Metal catalysis; Metallopolymers; Solvent effect

Indexed keywords

EID: 0003509525     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199806)1998:6<1143::aid-ejoc1143>3.0.co;2-u     Document Type: Article

References (43)

1. [1a] J. S. Lippard, M. J. Berg, Principles of Bioinorganic Chemistry, University Science Books, Mill Valley, CA, 1994, pp. 257-281.
2. [1b] D. E. Wilcox, Chem. Rev. 1996, 96, 2435.
3. [1c] N. Sträter, W. N. Lipscomb, T. Klabunde, B. Krebs, Angew. Chem. Int Ed. Eng. 1996, 35, 2024.
4. [2a] J. M. Berg, Acc. Chem. Res. 1995, 28, 14.
5. [2b] B. L. Vallee, D. S. Auld, Acc. Chem. Res. 1993, 26, 543.
6. P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, Tetrahedron 1995, 51, 527.
7. 1H-NMR analysis of the crude of the polymerization reaction does not reveal any detectable amount of unreacted dialdehyde or diamine.
8. E. Schnabel, Ann. 1964, 673, 171.
9. B. Siegel, R. Breslow, J. Am. Chem. Soc. 1975, 97, 6869.
10. Y. Couturier, C. Petitfaux, Bull. Soc. Chim. France 1978, I-435.
11. P. Scrimin, P. Tecilla, U. Tonellato, T. Vendrame, J. Org. Chem. 1989, 54, 5988.
12. K. J. Laidler, P. S. Bunting, The Chemical Kinetics of Enzyme Action, 2nd ed., Clarendon, Oxford, 1973; Chapter 11.
13. One of the reviewers pointed out whether the interactions involved in the media used in the present study are mainly London dispersion forces and do not contain a real hydrophobic component. His observation is well founded although we like to mention that rate constants (log kψ) are linear against the solvophobic scale, Sp, of Abraham (see: M. H. Abraham, L. P. Grellier, R. A. Mc Gill, J. Chem Soc., Perkin Trans. 2 1988, 339). No speculation on this point has been made in the text because of the limited number of solvent mixtures examined.
14. [11a] J. H. Fendler, Membrane Mimetic Chemistry, Wiley, New York, 1982; Chapter 2. - Metalloaggregates:
15. [11b] W. Tagaki, K. Ogino, Top. Curr. Chem. 1985, 128, 144.
16. [11c] P. Scrimin, P. Tecilla, U. Tonellato J. Org. Chem. 1991, 56, 161.
17. [11d] R. Fornasier, P. Scrimin, P. Tecilla, U. Tonellato J. Am. Chem. Soc. 1989, 111, 224.
18. [11e] P. Scrimin, P. Tecilla, U. Tonellato, J. Org. Chem 1994, 59, 18.
19. [11f] P. Scrimin, P. Tecilla, U. Tonellato J Org. Chem. 1994, 59, 4194.
20. [11g] J. G. J. Weijnen, A. Koudijs, J. F. J. Engbersen J. Chem. Soc., Perkin Trans. 2 1992, 829.
21. [11h] J. G. J. Weijnen, A. Koudijs, J. F. J. Engbersen J. Org. Chem. 1992, 57, 7259.
22. [11i] F. M. Menger,L. H. Gan, E. Johnson, D. H. Durst J. Am. Chem. Soc. 1987, 109, 2800.
23. R. Varadaraj, J. Bock, N. Brons, S. Pace, J. Phys. Chem. 1993, 97, 12991 and references therein.
24. L. G. Ionescu, L. S. Romanesco, F. Nome in Surfactants in Solution, vol. 2, K. L. Mittal, B. Lindman eds., Plenum, New York, 1984, pp. 789-803 and references cited therein.
25. The ester of γ-amino butanoic acid could not be studied because of the very fast concurrent cyclization to the corresponding γ-lactam.
26. II ions with this ester.
27. [16a] M. J. Young, D. Wahnon, R. C. Hynes, J. Chin, J Am. Chem. Soc. 1995, 117, 9441.
28. [16b] W R. W. Hay in Comprehensive Coordination Chemistry, G. Wilkinson, R. D. Gillard, J. McCleverty eds., vol. 2, Pergamon Press, Oxford, 1987, p. 413.
29. C. A. Bunton, P. Scrimin, P. Tecilla. J Chem. Soc., Perkin Trans. 2 1996, 419.
30. G. M. Loudon, J. Chem Ed. 1991, 68, 973.
31. a for the ammonium group of β-alanine is 10.1 (see: R. M. Smith, A. E. Martell, Critical Stability Constants, Plenum, New York, 1989.). It will likely decrease by coordination to the metal center.
32. K. H. Connors, Binding Constants, The Measurement of Molecular Complex Stability, Wiley, New York, 1975.
33. 7).
34. A. Fehrst, Enzyme Structure and Mechanism, Freeman, Reading, 1977.
35. For examples of metal ions-induced conformational changes of molecular receptors see: [23a] P. Tecilla, U. Tonellato, A. Veronese, F. Felluga, P. Scrimin. J. Org. Chem. 1997, 62, 7621. [23b] P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, J. Am. Chem. Soc. 1996, 118, 2505. [23c] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669. [23d] P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, J. Chem. Soc., Chem. Commun. 1995, 1163. [23e] P. Scrimin, P. Tecilla, U. Tonellato, N. Vignaga, J. Chem. Soc., Chem. Commun. 1991, 449.
36. For examples of metal ions-induced conformational changes of molecular receptors see: [23a] P. Tecilla, U. Tonellato, A. Veronese, F. Felluga, P. Scrimin. J. Org. Chem. 1997, 62, 7621. [23b] P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, J. Am. Chem. Soc. 1996, 118, 2505. [23c] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669. [23d] P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, J. Chem. Soc., Chem. Commun. 1995, 1163. [23e] P. Scrimin, P. Tecilla, U. Tonellato, N. Vignaga, J. Chem. Soc., Chem. Commun. 1991, 449.
37. For examples of metal ions-induced conformational changes of molecular receptors see: [23a] P. Tecilla, U. Tonellato, A. Veronese, F. Felluga, P. Scrimin. J. Org. Chem. 1997, 62, 7621. [23b] P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, J. Am. Chem. Soc. 1996, 118, 2505. [23c] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669. [23d] P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, J. Chem. Soc., Chem. Commun. 1995, 1163. [23e] P. Scrimin, P. Tecilla, U. Tonellato, N. Vignaga, J. Chem. Soc., Chem. Commun. 1991, 449.
38. For examples of metal ions-induced conformational changes of molecular receptors see: [23a] P. Tecilla, U. Tonellato, A. Veronese, F. Felluga, P. Scrimin. J. Org. Chem. 1997, 62, 7621. [23b] P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, J. Am. Chem. Soc. 1996, 118, 2505. [23c] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669. [23d] P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, J. Chem. Soc., Chem. Commun. 1995, 1163. [23e] P. Scrimin, P. Tecilla, U. Tonellato, N. Vignaga, J. Chem. Soc., Chem. Commun. 1991, 449.
39. For examples of metal ions-induced conformational changes of molecular receptors see: [23a] P. Tecilla, U. Tonellato, A. Veronese, F. Felluga, P. Scrimin. J. Org. Chem. 1997, 62, 7621. [23b] P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, J. Am. Chem. Soc. 1996, 118, 2505. [23c] B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669. [23d] P. Scrimin, P. Tecilla, U. Tonellato, G. Valle, A. Veronese, J. Chem. Soc., Chem. Commun. 1995, 1163. [23e] P. Scrimin, P. Tecilla, U. Tonellato, N. Vignaga, J. Chem. Soc., Chem. Commun. 1991, 449.
40. M. Wall, C. R. Hynes, J. Chin, Angew. Chem. Int. Ed. Engl. 1993, 32, 1633.
41. P. Molenveld, S. Kapsabelis, J. F. J. Engbersen, D. N. Reinhoudt, J. Am. Chem. Soc. 1997, 119, 2948.
42. Z. Holzbecher Handbook of Organic Reagents in Inorganic Analysis, Wiley, Chichester, 1976.
43. R. J. Leatherbarrow, Enzfitter, Elsevier, Amsterdam, 1987.