Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents

Chemistry - A European Journal

Volumn 14, Issue 26, 2008, Pages 7822-7827

  Gross, Dustin E ^a   Schmidtchen, Franz P ^b   Antonius, Wiebke ^b   Gale, Philip A ^c   Lynch, Vincent M ^a   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Anions; Calix 4 pyrrole; Calorimetry; Cations; Ion pairing

Indexed keywords

BIOCHEMISTRY; DICHLOROMETHANE; NEGATIVE IONS; NITROGEN COMPOUNDS; POSITIVE IONS; SOLVENTS;

ANIONS; CALIX[4]PYRROLE; CALORIMETRY; CATIONS; ION PAIRING;

HALOGENATION;

CALIX(4)PYRROLE; CALIXARENE; CATION; PORPHYRIN; QUATERNARY AMMONIUM DERIVATIVE; SOLVENT;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; TITRIMETRY; X RAY CRYSTALLOGRAPHY;

ALKYLATION; CALIXARENES; CATIONS; CRYSTALLOGRAPHY, X-RAY; HALOGENATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PORPHYRINS; QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS; TITRIMETRY;

EID: 53849125842     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800899     Document Type: Article

References (44)

1. J. L. Sessler, P. A. Gale, W. S. Cho, Anion Receptor Chemistry, RSC, Cambridge, 2006.
2. P. A. Gale, R. Quesada, Coord. Chem. Rev. 2006, 250, 3219-3244.
3. K. Bowman-James, Acc. Chem. Res. 2005, 38, 671-678.
4. a) F. P. Schmidtchen, Top. Curr. Chem. 2005, 255, 1-29;
5. b) F.P. Schmidtchen, Coord. Chem. Rev. 2006, 250, 2918-2928;
6. a) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
7. Angew. Chem. Int. Ed. 2001, 40, 486-516;
8. b) P. A. Gale, Coord. Chem. Rev. 2003, 240, 191-221.
9. P. A. Gale, S. E. García-Garrido, J. Garric. Chem. Soc. Rev. 2008, 37, 151-190.
10. J. M. Mahoney, G. U. Nawaratna, A. M. Beatty, P. J. Duggan, B. D. Smith, Inorg. Chem. 2004, 43, 5902-5907.
11. K. A. Byriel, V. Gasperov, K. Gloe, C. H. L. Kennard, A. J. Leong, L. F. Lindoy, M. S. Mahinay, H. T. Pham, P. A. Tasker, D. Thorp, P. Turner, J. Chem. Soc. Dalton Trans. 2003, 3034-3040.
12. G. Cafeo, C. Gargiulli, G. Gattuso, F. H. Kohnke, A. Notti, S. Occhipinti. S. Pappalardo, M. F. Parisi. Tetrahedron Lett. 2002, 43, 8103-8106.
13. G. Cafeo, G. Gattuso, F. H. Kohnke, A Notti, S. Occhipinti, S. Pappalardo, M. F. Parisi, Angew. Chem. 2002, 114, 2226-2230;
14. Angew. Chem. Int. Ed. 2002, 41, 2122-2126.
15. Q. S. Qian, O.S. Wilson, K. Bowman-James, H.H. Girault, Anal. Chem. 2001, 73, 497-503.
16. K. Kavallieratos, B. A. Moyer, Chem. Commun. 2001, 1620-1621.
17. K. Kavallieratos, R. A. Sachleben, G.J. van Berkel, B. A. Mover, Chem. Commun. 2000, 187-188.
18. G.J. Kirkovits, J. A. Shriver, P.A. Gale, J. L. Sessler, J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 69-75.
19. B. D. Smith, Ion Pair Recognition by Ditopic Receptors, in Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer, Dordrecht, 2005, pp. 137-152.
20. M. K. Chae, J.-I. Lee, N.-K. Kim, K.-S. Jeong. Tetrahedron Lett. 2007, 48, 6624-6627.
21. J. M. Mahoney, A. M. Beatty, B. D. Smith, J. Am. Chem. Soc. 2001, 123, 5847-5848.
22. J. M. Mahoney, K. A. Stucker, H. Jiang, I. Carmichael, N. R. Brinkmann, A. M. Beatty, B. C. Noll B. D. Smith, J. Am. Chem. Soc. 2005, 127, 2922-2928.
23. G. Tumcharern, G.; T. Tuntulani, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Org. Lett. 2003, 5, 4971-4974.
24. J. Scheerder, J. P. M. von Duynhoven, J. F. J Engbersen, D. N. Reinhoudt, Angew. Chem. 1996, 108, 1172-1175;
25. Angew. Chem. Int. Ed. Engl. 1996, 35, 1090-1093.
26. R. Shukla, T. Kida, B. D. Smith, Org. Lett. 2000, 2, 3099-3102.
27. R. Custelcean, L. H. Delmau, B. A. Moyer, J. L. Sessler, W.-S. Cho, D. Gross, G. W. Bates, S. J. Brooks, M. E. Light, P. A. Gale, Angew. Chem. 2005, 117, 2593-2598;
28. Angew. Chem. Int. Ed. 2005, 44, 2537-2542.
29. a) G. W. Bates, P. A. Gale, M. E. Light, CrystEngComm 2006, 8, 300-302;
30. b) G. W. Bates, P. A. Gale, M. E. Light, Supramol. Chem. 2008, 20, 23-28.
31. M. P. Wintergerst, T. G. Levitskaia, B. A. Moyer. J. L. Sessler, L. H. Delmau, J. Am. Chem. Soc. 2008, 130, 4129-4139.
32. J. L. Sessler, D. E. Gross, W.-S. Cho, V. M. Lynch, F. P. Schmidtchen, G. W. Bates, M. E. Light, P. A. Gale,.J. Am. Chem. Soc. 2006, 128, 12281-12288.
33. E. A. Arafa, K. I. Kinnear, J. C. Lockhart, J. Chem. Soc. Chem. Commun. 1992, 61-64.
34. T. Tozawa, Y. Misawa, S. Tokita, Y. Kubo, Tetrahedron Lett. 2000, 41, 5219-5223.
35. a) S. Kubik, J. Am. Chem. Soc. 1999, 121, 5846-5855;
36. b) S. Kubik, R. Goddard, J. Org. Chem. 1999, 64, 9475-9486;
37. c) G. Heinrichs, S. Kubik, J. Lacour, L. Vial, J. Org. Chem. 2005, 70, 4498-4501.
38. C. S. Wilcox, in Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr). VCH, Weinheim (Germany), 1991, pp. 123-143.
39. a) W. F. van Gunsteren, S. R. Billeter, A.A. Eising, P.H. Hünenberger, P. Krüger, A. E. Mark, W. R. P. Scott, I. G. Tironi, Biomoleeular simulation: The GROMOS96 manual and user guide. Hochschulverlag AG, ETH-Zürich, 1996;
40. b) R. G. Lins, P. H. Hünenberger, J. Comput. Chem. 2005, 26, 1400-1412.
41. a) P. A. Gale, J. L. Sessler, V. Kral. Chem. Commun. 1998, 1-8:
42. b) P. A. Gale, P. Anzenbacher, Jr.. J. L. Sessler, Coord. Chem. Rev. 2001, 222, 57-102.
43. R. D. Bach, O. Dmitrenko, M. K. Glukhovtsev, J. Am. Chem. Soc. 2001, 123, 7134-7145.
44. M. Christen, P. H. Hünenberger, D. Bakowies, R. Baron, D. P. Geerke, T. N. Heinz, M. A. Kastenholz, V. Kräutler, C. Oostenbrink, C. Peter, D. Trzesniak, W. F. van Gunsteren, J. Comput. Chem. 2005, 26, 1719-1751.