(cis)-5,10,15,20-Tetrakis[2-(arylurea)phenyl]porphyrins: Novel neutral ligands for remarkably selective and exceptionally strong chloride anion complexation in (CD3)2SO

Chemical Communications

Volumn , Issue 17, 1997, Pages 1685-1686

  Jagessar, Raymond C ^a   Burns, Dennis H ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542790469     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702389h     Document Type: Article

References (23)

1. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
2. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
3. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
4. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
5. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
6. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
7. For reviews, see (a) R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 1995, 95, 2529; (b) B. Dietrich, Pure Appl. Chem., 1993, 65, 1457. For more recent examples (but by no means a comprehensive list), see (c) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H., Crabtree, J. Am. Chem. Soc., 1997, 119, 2325; (d) A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793; (e) M. Berger and F. P. Schmidtchen, J. Am. Chem. Soc., 1996, 118, 8947; (f) V. Král, H. Furuta, K. Schreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595; (g) P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.
8. J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro and D. N. Reinhoudt, J. Org. Chem., 1995, 60, 6448.
9. P. Bühlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron, 1997, 53, 1647.
10. J. Scheerder, M. Fochi, J. F. J. Engbersen and D. N. Reinhoudt, J. Org. Chem., 1994, 59, 7815.
11. E. Fan, S. A. Van Arman, S. Kincaid and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 369.
12. B. C. Hamann, N. R. Branda and J. Rebek, Tetrahedron Lett., 1993, 34, 6837.
13. L. Stryer, Biochemistry, W. H. Freeman, New York, 1988, pp. 963-964; J. W. Hanrahan, J. A. Tabcharani, F. Becq, C. J. Mathews, O. Augustinas, T. J. Jensen, X.-B. Chang and J. R. Riordan, in Ion Channels and Genetic Diseases, ed. D. C. Dawson and R. A. Frizzel, Rockefeller University Press, New York, 1995.
14. L. Stryer, Biochemistry, W. H. Freeman, New York, 1988, pp. 963-964; J. W. Hanrahan, J. A. Tabcharani, F. Becq, C. J. Mathews, O. Augustinas, T. J. Jensen, X.-B. Chang and J. R. Riordan, in Ion Channels and Genetic Diseases, ed. D. C. Dawson and R. A. Frizzel, Rockefeller University Press, New York, 1995.
15. P. D. Beer, M. G. B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc., Chem. Commun., 1995, 1187; P. D. Beer, Chem. Commun., 1996, 689; P. D. Beer, M. G. B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 1997, 881.
16. P. D. Beer, M. G. B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc., Chem. Commun., 1995, 1187; P. D. Beer, Chem. Commun., 1996, 689; P. D. Beer, M. G. B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 1997, 881.
17. P. D. Beer, M. G. B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc., Chem. Commun., 1995, 1187; P. D. Beer, Chem. Commun., 1996, 689; P. D. Beer, M. G. B. Drew and R. Jagessar, J. Chem. Soc., Dalton Trans., 1997, 881.
18. T. N. Sorrell, Inorg. Synth., 1980, 20, 163.
19. J. S. Lindsey, J. Org. Chem., 1980, 45, 5215.
20. A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem., 1967, 32, 476.
21. The computer program EQNMR was used to calculate binding constants: M. J. Hynes, J. Chem. Soc., Dalton Trans., 1993, 311.
22. -1 cannot be determined accurately: T. Wang, J. S. Bradshaw and R. M. Izatt, J. Heterocycl. Chem., 1994, 31, 1097.
23. K. A. Connors, Binding Constants, Wiley. New York, 1987, pp. 24-28.