A tri-armed sulfonamide host for selective binding of chloride

New Journal of Chemistry

Volumn 27, Issue 1, 2003, Pages 172-177

  Hettche, Frank ^a   Hoffmann, Reinhard W ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 (2 AZIDO 1 METHYLETHYL) 1,3,5 TRIAZINE 2,4,6 TRIONE; ANION; CHLORIDE; NITRATE; SULFONAMIDE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHLORIDE TRANSPORT; COMPLEX FORMATION; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037242388     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b206125m     Document Type: Article

References (44)

1. (a) R. W. Hoffmann, Angew. Chem., 1992, 104, 1147; R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 1124;
2. (a) R. W. Hoffmann, Angew. Chem., 1992, 104, 1147; R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 1124;
3. (b) R. W. Hoffmann, Angew. Chem., 2000, 112, 2134; R. W. Hoffmann, Angew. Chem., Int. Ed., 2000, 39, 2054.
4. (b) R. W. Hoffmann, Angew. Chem., 2000, 112, 2134; R. W. Hoffmann, Angew. Chem., Int. Ed., 2000, 39, 2054.
5. (a) P. W. Smith and W. C. Still, J. Am. Chem. Soc., 1988, 110, 7917;
6. (b) M. Wilstermann, J. Balogh and G. Magnusson, J. Org. Chem., 1997, 62, 3659;
7. (c) D. R. Bundle, R. Alibés, S. Nilar, A. Otter, M. Warwas and P. Zhang, J. Am. Chem. Soc., 1998, 120, 5317;
8. (d) J. L. Jiménez Blanco, J. M. Benito, C. Ortiz Mellet and J. M. Garcia Fernández, Org. Lett., 1999, 1, 1217;
9. (e) K. S. Jeong, J. W. Lee, T.-Y. Park and S.-Y. Chang, J. Chem. Soc., Chem. Commun., 1999, 2069 and references therein.
10. D. J. Cram, Angew. Chem., 1986, 98, 1041; D. J. Cram, Angew. Chem., Int. Ed. Engl., 1986, 25, 1039.
11. D. J. Cram, Angew. Chem., 1986, 98, 1041; D. J. Cram, Angew. Chem., Int. Ed. Engl., 1986, 25, 1039.
12. (a) J. Scheerder, J. F. J. Engbersen and D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas, 1996, 115, 307;
13. (b) F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609;
14. (c) M. M. G. Antonisse and D. N. Reinhoudt, Chem. Commun., 1998, 443;
15. (d) P. D. Beer and P. A. Gale, Angew. Chem., 2001, 113, 502; P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 486.
16. (d) P. D. Beer and P. A. Gale, Angew. Chem., 2001, 113, 502; P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 486.
17. R. W. Hoffmann, F. Hettche and K. Harms, Chem. Commun., 2002, 782.
18. H. Sugimoto, Y. Yamane and S. Inoue, Tetrahedron: Asymmetry, 2000, 11, 2067.
19. (a) F. Johnson, Chem. Rev., 1968, 68, 375;
20. (b) R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.
21. E. Fan, S. A. Van Arman, S. Kincaid and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 369.
22. A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793.
23. A. J. Ayling, M. N. Pérez-Payan and A. P. Davis, J. Am. Chem. Soc., 2001, 123, 12 716; A. J. Ayling, S. Broderick, J. P. Clare, A. P. Davis, M. N. Pérez-Payán, M. Lahtinen, M. J. Nissinen and K. Rissanen, Chem. Eur. J., 2002, 8, 2197 and references therein.
24. A. J. Ayling, M. N. Pérez-Payan and A. P. Davis, J. Am. Chem. Soc., 2001, 123, 12 716; A. J. Ayling, S. Broderick, J. P. Clare, A. P. Davis, M. N. Pérez-Payán, M. Lahtinen, M. J. Nissinen and K. Rissanen, Chem. Eur. J., 2002, 8, 2197 and references therein.
25. M. Mascal, A. Armstrong and M. D. Bartberger, J. Am. Chem. Soc., 2002, 124, 6274.
26. H. B. Bürgi, J. D. Dunitz and E. Shefer, J. Am. Chem. Soc., 1973, 95, 5065.
27. N. Knouzi, M. Vaultier and R. Carrié, Bull. Soc. Chim. Fr., 1985, 815.
28. (a) H. Ulrich, in Cycloadditions of Heterocumulenes, Academic Press, New York, 1967 p. 128;
29. (b) for leading references see: J. Tang, T. Mohan and J. C. Verkade, J. Org. Chem., 1994, 59, 4931.
30. 5.
31. (a) R. Jairam and P. G. Potvin, J. Org. Chem., 1992, 57, 4136;
32. (b) C. Raposo, M. Almaraz, M. Martin, V. Weinrich, M. L. Mussóns, V. Alkázar, M. C. Caballero and J. R. Morán, Chem. Lett., 1995, 759;
33. (c) H. Xie, S. Yi, X. Yang and S. Wu, New J. Chem., 1999, 23, 1105;
34. (d) F. Werner and H. J. Schneider, Helv. Chim. Acta, 2000, 83, 465.
35. S. Valiyaveettil, J. F. J. Engbersen and D. N. Reinhoud, Angew. Chem., 1993, 105, 942; S. Valiyaveettil, J. F. J. Engbersen and D. N. Reinhoud, Angew. Chem., Int. Ed. Engl., 1993, 23, 900.
36. S. Valiyaveettil, J. F. J. Engbersen and D. N. Reinhoud, Angew. Chem., 1993, 105, 942; S. Valiyaveettil, J. F. J. Engbersen and D. N. Reinhoud, Angew. Chem., Int. Ed. Engl., 1993, 23, 900.
37. R. W. Hoffmann, D. Stenkamp, T. Trieselmann and R. Göttlich, Eur. J. Org. Chem., 1999, 2915.
38. P. E. Hansen, Progr. NMR Spectrosc., 1981, 14, 175.
39. SPSS Inc. 2000, We thank Prof. A. P. Davis (Bristol) and Prof. H.-J. Schneider (Saarbrücken) for special routines to analyse 1:1 complexes.
40. M. Haj-Zaroubi, N. W. Mitzel and F. P. Schmidtchen, Angew. Chem., 2002, 114, 111; M. Haj-Zaroubi, N. W. Mitzel and F. P. Schmidtchen, Angew. Chem., Int. Ed., 2002, 41, 104 and references therein.
41. M. Haj-Zaroubi, N. W. Mitzel and F. P. Schmidtchen, Angew. Chem., 2002, 114, 111; M. Haj-Zaroubi, N. W. Mitzel and F. P. Schmidtchen, Angew. Chem., Int. Ed., 2002, 41, 104 and references therein.
42. K. A. Connors, in Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davis, D. D. MacNicol and F. Vögtle, Pergamon Press, Oxford, 1996, vol. 3, p. 233.
43. B. R. Linton, M. S. Goodman, E. Fan, S. A. Van Arman and A. D. Hamilton, J. Org. Chem., 2001, 66, 7313.
44. F. Hettche, P. Reiss and R. W. Hoffmann, Chem. Eur. J., 2002, 8, 4946.