Complexation of fullerenes by calix[n]arenes: Molecular dynamic simulations and Benesi-Hildebrand equilibrium constants

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 14931-14940

  Schlachter, Ingo ^a,d   Höweler, Udo ^a   Iwanek, Waldemar ^b   Urbaniak, Mariusz ^b   Mattay, Jochen ^c  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b JAN KOCHANOWSKI UNIVERSITY   (Poland)

^c BIELEFELD UNIVERSITY   (Germany)

^d EVONIK INDUSTRIES AG   (Germany)

Author keywords

Benesi Hildebrand; Calix n arene; Complexation; Fullerene; MD Simulations

Indexed keywords

CALIXARENE; FULLERENE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; SYNTHESIS;

ARENE;

EID: 0033601462     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00967-9     Document Type: Article

References (39)

1. a) I. Schlachter, taken in part from the Ph.D. thesis, Universität Münster, 1995.
2. b) For a preliminary report see: J. Averdung, T. Budwach, W. Iwanek, I. Schlachter, G. Torres-Garcia, J. Mattay in Progress in Fullerene Research, H. Kuzmany et al. (Eds.), World Scientific Singapore, 1995, p. 137-141.
3. a) H.W. Kroto, J.R. Heath, S.C. O'Brien, R.F. Curl, R.E. Smalley, Nature 1985, 318, 162-163.
4. b) H.W. Kroto, Angew. Chem. 1992, 104, 113-252; Angew. Chem. Int. Ed. Engl. 1992, 31, 111.
5. b) H.W. Kroto, Angew. Chem. 1992, 104, 113-252; Angew. Chem. Int. Ed. Engl. 1992, 31, 111.
6. W. Krätschmer, L.D. Lamb, K. Fostiropoulos, D.R. Huffman, Nature 1990, 347, 354-358.
7. a) A. Hirsch, Chem. Unserer Zeit 1994, 28, 79-87.
8. b) A. Hirsch, The chemistry of fullerenes, Thieme Verlag, Stuttgart 1994.
9. a) J. Averdung, G. Torres-Garcia, H. Luftmann, I. Schlachter, J. Mattay, Full.Sci.Techn. 1996, 4, 633-654.
10. b) J. Mattay, G. Torres-Garcia, J. Averdung, C. Wolff, I. Schlachter, H. Luftmann, C. Siedschlag, P. Luger, M. Ramm, J. Phys.chem. Solids, 1997, 58, 1929-1937.
11. c) J. Averdung, J. Mattay, Praxis der Naturwissenschaften Chemie 1997, 46, 28-34.
12. For a spectacular example of an endohedral fullerene compound containing atomic nitrogen see: H. Mauser, N.v.E. Hommes, T. Clark, A. Hirsch, B. Pietzak, A. Weidinger, L. Dunsch, Angew. Chem. 1997, 109, 2858-2861; Angew. Chem. Int. Ed. Engl. 1997, 36, 2835-2838.
13. For a spectacular example of an endohedral fullerene compound containing atomic nitrogen see: H. Mauser, N.v.E. Hommes, T. Clark, A. Hirsch, B. Pietzak, A. Weidinger, L. Dunsch, Angew. Chem. 1997, 109, 2858-2861; Angew. Chem. Int. Ed. Engl. 1997, 36, 2835-2838.
14. J. Averdung, H. Luftmann, I. Schlachter, J. Mattay, Tetrahedron 1995, 51, 6977-6982
15. T. Grösser, M. Prato, V. Lucchini, A. Hirsch, F. Wudl, Angew. Chemie 1995, 107, 1462-1464; Angew. Chem. Int. Ed. Engl. 1995, 34, 1343-1345.
16. T. Grösser, M. Prato, V. Lucchini, A. Hirsch, F. Wudl, Angew. Chemie 1995, 107, 1462-1464; Angew. Chem. Int. Ed. Engl. 1995, 34, 1343-1345.
17. E.C. Constable, Angew. Chemie 1994, 106, 2359-2361; Angew. Chem. Int. Ed. Engl. 1994, 33, 2269-2271.
18. E.C. Constable, Angew. Chemie 1994, 106, 2359-2361; Angew. Chem. Int. Ed. Engl. 1994, 33, 2269-2271.
19. T. Andersson, G. Westman, O. Wennerström, M. Sundahl, J. Chem. Soc., Perkin Trans. 2 1994, 1097-1101.
20. R.M. Williams, J.W. Verhoeven, Recl. Trav. Chim. Pays-Bas 1992, 11, 531-532.
21. J. Atwood, G.A. Koutsantonis, C.L. Raston, Nature 1994, 368, 229-231.
22. T. Suzuki, K. Nakashima, S. Shinkai, Chem. Lett. 1994, 699-702.
23. J.L. Atwood, L.J. Barbour, P.J. Nichols, C.L. Raston, C.A. Sandoval, Chem. Eur.J. 1999, 5, 990-996 and refs. therein.
24. V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745 and literature cited therein.
25. V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745 and literature cited therein.
26. P. Timmerman, W. Verboom, D.N. Reinhoudt, Tetrahedron 1996, 52, 2663-2704.
27. a) S.J. Weiner, P.A. Kollman, D.A. Case, U.C. Singh, C. Ghio, G. Alagona, S. Profeta Jr., P. Weiner, J. Am. Chem. Soc. 1984, 106, 765-784
28. b) AMBER, 3.0: U.C. Singh, P.K. Weiner, J. Caldwell, P.A. Kollman, University of California, San Francisco, 1987.
29. P.D. Grootenhuis, P.A. Kollman, L.C. Groenen, D.N. Reinhoudt, G.J. van Hummel, F Ugozzoli, G. Andreetti, J. Am. Chem. Soc. 1990, 112, 4165-4176.
30. S. Fischer, P.D. Grootenhuis, L.C. Groenen, W.P. van Hoorn, F.C. Van Veggel, D.N. Reinhoudt, M. Karplus, J. Am. Chem. Soc. 1995, 117, 1611-1620.
31. a) I. Schlachter, J. Mattay, J. Suer, U. Höweler, G. Würthwein, E.-U. Würthwein, Tetrahedron, 1997, 53, 119-132.
32. b) U. Höweler, T. Bäcker, M. Klessinger, M. Eckert-Maksic, Z.B. Maksic, Croat. Chem. Acta 1990, 64, 539-549.
33. c) Program MAXIMOBY 3.3: Implementation of force field and semiempirical methods for calculation of structures and properties of large chemical systems. Current Version 5.1, CHEOPS, U. Höweler, 48341 Altenberge, Germany (e-mail: hoeweler@muenster.de).
34. H. A. Benesi, J.H. Hildebrand, J. Am Chem. Soc. 1949, 71, 2703-2707.
35. a) J.W. Steed, P.C. Junk, J.L. Atwood, M.J. Barnes, C.L. Raston, R.S. Burkhalter, J. Am. Chem.Soc. 1994, 10346-10347.
36. b) J.L. Atwood, M.J. Barnes, M.G. Gardiner, C.L. Raston, Chem. Commun. 1996, 1449-1450.
37. A. Ikeda, M. Yoshimura, S. Shinkai, Tetrahedron Lett. 1997, 38, 2107-2110.
38. See also ref. 14: p. 994-995.
39. C.D. Gutsche et al. in Organic Synthesis, Coll. Vol. 8, J.P. Freeman et al. (Eds.), 1993, p. 75-77, p. 77-79, and p. 80-81.