Modulation of cation binding in calix[4]arene amides: Synthesis, complexation and molecular modelling studies

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 8, 1999, Pages 1727-1738

  Arnaud Neu, Françoise ^a   Barboso, Silvia ^a   Berny, Frédéric ^c   Casnati, Alessandro ^b   Muzet, Nicolas ^c   Pinalli, Alessandra ^b   Ungaro, Rocco ^b   Schwing Weill, Marie José ^a   Wipff, Georges ^c  

^a CNRS   (France)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346541806     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902001b     Document Type: Article

References (54)

1. G. D. Andreetti, F. Ugozzoli, A. Pochini and R. Ungaro, in Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D MacNicol, Oxford University Press, Oxford, 1991, vol. 4, pp. 64-125; R. Ungaro and A. Pochini, in Topics in Inclusion Science. Calixarenes, a Versatile Class of Macrocyclic Compounds, ed. V. Böhmer and J. Vicens, Kluwer Academic Publishers, Dordrecht, 1990, pp. 127-145; M. J. Schwing and M. A. McKervey, ibid., pp. 149-171; A. McKervey, M. J. Schwing-Weill and F. Arnaud-Neu, in Comprehensive Supramoleculur Chemistry, ed. G. W. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 537-603.
2. G. D. Andreetti, F. Ugozzoli, A. Pochini and R. Ungaro, in Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D MacNicol, Oxford University Press, Oxford, 1991, vol. 4, pp. 64-125; R. Ungaro and A. Pochini, in Topics in Inclusion Science. Calixarenes, a Versatile Class of Macrocyclic Compounds, ed. V. Böhmer and J. Vicens, Kluwer Academic Publishers, Dordrecht, 1990, pp. 127-145; M. J. Schwing and M. A. McKervey, ibid., pp. 149-171; A. McKervey, M. J. Schwing-Weill and F. Arnaud-Neu, in Comprehensive Supramoleculur Chemistry, ed. G. W. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 537-603.
3. G. D. Andreetti, F. Ugozzoli, A. Pochini and R. Ungaro, in Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D MacNicol, Oxford University Press, Oxford, 1991, vol. 4, pp. 64-125; R. Ungaro and A. Pochini, in Topics in Inclusion Science. Calixarenes, a Versatile Class of Macrocyclic Compounds, ed. V. Böhmer and J. Vicens, Kluwer Academic Publishers, Dordrecht, 1990, pp. 127-145; M. J. Schwing and M. A. McKervey, ibid., pp. 149-171; A. McKervey, M. J. Schwing-Weill and F. Arnaud-Neu, in Comprehensive Supramoleculur Chemistry, ed. G. W. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 537-603.
4. G. D. Andreetti, F. Ugozzoli, A. Pochini and R. Ungaro, in Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D MacNicol, Oxford University Press, Oxford, 1991, vol. 4, pp. 64-125; R. Ungaro and A. Pochini, in Topics in Inclusion Science. Calixarenes, a Versatile Class of Macrocyclic Compounds, ed. V. Böhmer and J. Vicens, Kluwer Academic Publishers, Dordrecht, 1990, pp. 127-145; M. J. Schwing and M. A. McKervey, ibid., pp. 149-171; A. McKervey, M. J. Schwing-Weill and F. Arnaud-Neu, in Comprehensive Supramoleculur Chemistry, ed. G. W. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 537-603.
5. S. Fanni, F. Arnaud-Neu, M. A. McKervey, M. J. Schwing-Weill and K. Ziat, Tetrahedron Lett., 1996, 37, 7975.
6. A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, G. D. Andreetti, G. Calestani and F. Ugozzoli, J. Inclusion Phenom., 1988, 6, 119.
7. F. Arnaud-Neu, M. J. Schwing-Weill, K. Ziat, S. Cremin, S. J. Harris and M. A. McKervey, New J. Chem., 1991, 15, 33.
8. H. Sigel and R. B. Martin, Chem. Rev., 1982, 82, 385.
9. F. Arnaud-Neu, G. Barrett, S. Fanni, D. Marrs, W. McGregor, M. A. McKervey, M. J. Schwing-Weill, V. Vetrogon and S. Wechsler, J Chem. Soc., Perkin Trans. 2, 1995, 453.
10. S. K. Chang and I. Cho. Chem. Lett., 1987, 947.
11. Fourth European Conference on Management and Disposal of Radioactive Waste, EUR 17543 EN, ed. T. McMenamin, European Communities Publications, 1997.
12. A. Casnati, Y. Ting, D. Berti, M. Fabbi, A. Pochini, R. Ungaro, D. Sciotto and G. G. Lombardo, Tetrahedron, 1993, 49, 9815.
13. A. Casnati, C. Fischer, M. Guardigli, A. Isernia, I. Manet, N. Sabbatini and R. Ungaro, J. Chem Soc., Perkin Trans. 2, 1996, 395.
14. A. J. Speziale and P. C. Hamm, J. Am. Chem. Soc., 1956, 78, 2556.
15. H. A. Flashka, EDTA Titration, Pergamon Press, London, 1964.
16. A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M. J. Schwing, R. J. M. Egberink, F. de Jong and D. N. Reinhoudt, J. Am. Chem. Soc., 1995, 117, 2767.
17. V. I. Vetrogon, N. G. Lukyanenko, M. J. Schwing-Weill and F. Arnaud-Neu, Talanta, 1994, 41, 2105.
18. D. A. Pearlman, D. A. Case, J. C. Caldwell, W. S. Ross, T. E. Cheatham III, D. M. Ferguson, G. L. Seibel, U. C. Singh, P. Weiner and P. A. Kollman, AMBER4.1, University of California, San Francisco, CA, 1995.
19. P. A. Kollman, J. W. Caldwell, T. Fox, D. C. Spellmeyer, D. M. Ferguson, K. M. Merz, I. R. Gould, C. I. Bayly, P. Cieplak and W. D. Cornell, J. Am. Chem. Phys., 1995, 117, 5179.
20. N. Muzet, G. Wipff, A. Casnati, L. Domiano, R. Ungaro and F. Ugozzoli, J. Chem. Soc., Perkin Trans. 2, 1996, 1065.
21. W. L. Jorgensen and J. Tirado-Rives. J Am. Chem. Soc., 1988, 110, 1657.
22. G. Wipff and L. Troxler, 1st European Conference on Computational Chemistry, 1995, pp. 325-336; L. Troxler, J. M. Harrow-field and G. Wipff, J. Phys. Chem., 1998, 102, 6821.
23. G. Wipff and L. Troxler, 1st European Conference on Computational Chemistry, 1995, pp. 325-336; L. Troxler, J. M. Harrow-field and G. Wipff, J. Phys. Chem., 1998, 102, 6821.
24. J. Aqvist, J. Phys. Chem., 1990, 94, 8021.
25. W. L. Jorgensen, J. Chandrasekhar and J. D. Madura, J. Chem. Phys., 1983, 79, 926.
26. W. L. Jorgensen, J. M. Briges and M. L. Contreras, J. Phys. Chem., 1990, 94, 1683.
27. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
28. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
29. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
30. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
31. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
32. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
33. M. Lauterbach, E. Engler, N. Muzet, L. Troxler and G. Wipff, J. Phys. Chem., 1998, 102, 225; F. Berny, N. Muzet, R. Schurhammer, L. Troxler and G. Wipff, in Current Challenges in Supramolecular Assemblies, NATO ASI, ed. G. Tsoucaris, Kluwer Academic Publishers, Dordrecht, 1998, pp. 221-245 and references cited therein; F. Berny, N. Muzet, L. Troxler and G. Wipff, in Supramolecular Science: where it is and where it is going, NATO ASI, ed. R. Ungaro and E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999, pp. 95-125; Lauterbach and G. Wipff, in Physical Supramolecular Chemistry, ed. L. Echegoyen and A. Kaifer, Kluwer Academic Publishers, Dordrecht, 1996, pp. 65-102; N. Muzet, E. Engler and G. Wipff, J. Phys. Chem. B, 1998, 102, 10772; A. Varnek, L. Troxler and G. Wipff, Chem. Eur J., 1997, 3, 552; L. Troxler and G. Wipff, Anal. Sci., 1998, 14, 43.
34. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Reploge. R. Gomperts, F. Martin, D. J. J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzales and J. A. Pople, Gaussian 94, Revision B.2, Gaussian, Inc., Pittsburgh PA, 1995.
35. P. Kaupp, P. v. R. Schleyer, H. Stoll and H. Preuss, J. Chem. Phys., 1991, 94, 1360.
36. M. Dolg, H. Stoll and H. Preuss, J. Chem. Phys., 1989, 90, 1730.
37. S. F. Boys and F. Bernardi, Mol. Phys., 1970, 19, 553.
38. L. C. Groenen, B. H. M. Ruël, A. Casnati, P. Timmerman, W. Verboom, S. Harkema, A. Pochini, R. Ungaro and D. N. Reinhoudt, Tetrahedron Lett., 1991, 32, 2675; A. Arduini and A. Casnati, Calixarenes, in Macrocyclic Synthesis: a Practical Approach, ed. D. Parker, Oxford University Press, Oxford, 1996, pp. 145-173.
39. L. C. Groenen, B. H. M. Ruël, A. Casnati, P. Timmerman, W. Verboom, S. Harkema, A. Pochini, R. Ungaro and D. N. Reinhoudt, Tetrahedron Lett., 1991, 32, 2675; A. Arduini and A. Casnati, Calixarenes, in Macrocyclic Synthesis: a Practical Approach, ed. D. Parker, Oxford University Press, Oxford, 1996, pp. 145-173.
40. C. D. Gutsche and L. J. Bauer, J. Am. Chem. Soc., 1985, 107, 6052; C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto and C. Sanchez, J. Org Chem., 1991, 56, 3372.
41. C. D. Gutsche and L. J. Bauer, J. Am. Chem. Soc., 1985, 107, 6052; C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto and C. Sanchez, J. Org Chem., 1991, 56, 3372.
42. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink and D. N. Reinhoudt, Chem. Eur. J., 1996, 2, 436; I. Ikeda and S. Shinkai, J. Am. Chem. Soc., 1994, 116, 3102.
43. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink and D. N. Reinhoudt, Chem. Eur. J., 1996, 2, 436; I. Ikeda and S. Shinkai, J. Am. Chem. Soc., 1994, 116, 3102.
44. R. Taylor and O. Kennard, Acc. Chem. Res., 1984, 17, 320.
45. P. Murray-Rust and J. P. Glusker, J. Am. Chem. Soc., 1984, 106, 1018.
46. P. D. Beer, M. G. B. Drew, R. J. Knubley and M. I. Ogden, J. Chem. Soc., Dalton Trans., 1995, 3117.
47. G. Y. S. Chan, M. G. B. Drew, M. J. Hudson, P. B. Iveson, J.-O. Liljenzin, M. Skalberg, L. Spjuth and C. Madic, J. Chem. Soc., Dalton Trans. , 1997, 649.
48. N. Condamines and C. Musikas, Solv. Extract. Ion Exch., 1992, 10, 69.
49. S. Musikas, P. Vitorge, R. Fitoussi, M. Bonin and D. P. Vialard-Goudou, International Symposium on Actinide Recovery, 182nd National Meeting of the American Chemical Society, 1981, pp. 1-14.
50. R.-S. Tsai, W. Fan, N. El Tayar, P. A. Carrupt, B. Testa and L. B. Kier, J. Am. Chem. Soc. , 1993, 115, 9632.
51. G. Wipff and M. Lauterbach, Supramol. Chem., 1995, 6, 187.
52. G. Wipff, E. Engler, P. Guilbaud, M. Lauterbach, L. Troxler and A. Varnek, New J. Chem., 1996, 20, 403.
53. L. Dei, A. Casnati, P. L. Nostro, A. Pochini, R. Ungaro and P. Baglioni, Langmuir, 1996, 12, 1589.
54. Y. Ishikawa, T. Kaïnite, T. Matsuda, T. Otsuka and S. Shinkai, J. Chem. Soc., Chem. Commun., 1989, 736.