Facilitated transport of hydrophilic salts by mixtures of anion and cation carriers and by ditopic carriers

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10142-10151

  Chrisstoffels, Lysander A J ^a   De Jong, Feike ^a   Reinhoudt, David N ^a   Sivelli, Stefano ^b   Gazzola, Licia ^b   Casnati, Alessandro ^b   Ungaro, Rocco ^b  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CATION;

ACTIVE TRANSPORT; ARTICLE; DIFFUSION; EXTRACTION; HYDROPHILICITY; ION TRANSPORT; MEMBRANE TRANSPORT; MOLECULAR DYNAMICS; TRANSPORT KINETICS;

EID: 0033520683     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991588g     Document Type: Article

References (80)

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33. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
34. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
35. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
36. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
37. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
38. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
39. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
40. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
41. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
42. For recognition of salts by bifunctional receptors see: (a) Olsher, U.; Frolow, F.; Dalley, N. K.; Weiming, J.; Yu, Z.-Y.; Knobeloch, J. M.; Bartsch, R. A. J. Am. Chem. Soc. 1991, 113, 6570. (b) Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 1472 (c) Arafa, E. A.; Kinnear, K. I.; Lockhart, J. C. J. Chem. Soc., Chem. Commun. 1992, 61. (d) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (e) Kinnear, K. I.; Mousley, D. P.; Arafa, E.; Lockhart, J. C. J. Chem. Soc., Dalton Trans. 1994, 3637. (f) Reetz, M. T.; Johnson, B. M.; Harms, K. Tetrahedron Lett. 1994, 35, 2525. (g) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4069. (h) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 467. Beer, P. D.; Drew, M. G. B.; Knubley, R. J.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1995, 3117. (j) Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090.
43. Rudkevich, D. M.; Mercer-Chalmers, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124.
44. (a) Rudkevich, D. M.; Stauthamer, W. P. R. V.; Verboom, W.; Engbersen, J. F. J.; Harkema, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 9671.
45. (b) Rudkevich, D. M.; Verboom, W.; Brzozka, Z.; Palys, M.; Stauthamer, W. P. R. V.; van Hummel, G. J.; Franken, S. M.; Harkema, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 4341.
46. (c) Antonisse, M. M. G.; Snellink-Ruël, B. H. M.; Yigit, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1997, 62, 9034.
47. Chrisstoffels, L. A. J., Ph.D. Thesis, University of Twente, Enschede, The Netherlands, 1998.
48. Preliminary results were described in: Visser, H. C.; Rudkevich, D. M.; Verboom, W.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 11554 and ref 17.
49. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
50. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
51. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
52. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
53. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
54. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
55. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. (c) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. (d) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
56. For complexation studies by (thio)urea based receptors see: (a) Adrian J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1992, 114, 1398. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072. Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815. (e) Raposo, C.; Almaraz, M.; Martin, M.; Weinrich, V.; Mussons, L.; Alcazar, V.; Caballero, C.; Mosan, J. R. Chem. Lett. 1995, 759. (f) Wilcox, C. S.; Kim, E.-I.; Romano, S.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. (g) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. (h) Jagessar, R. C.; Burns, D. H. Chem. Commun. 1997, 1685.
57. Casnati, A.; Pochini, A.; Ungaro, R.; Bocchi, C.; Ugozzoli, F.; Egberink, R. J. M.; Struijk, W.; Lugtenberg, R. J. W.; de Jong, F., Reinhoudt, D. N. Chem. Eur. J. 1996, 2, 436.
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62. Lipophilic, branched alkyl chains were attached to provide sufficient lipophilicity and to increase the solubility of the carriers in organic solutions.
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64. m.
65. M.
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68. 4 transport takes place.
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71. This demonstrates that extraction of KCl by anion carrier 5 individually is much less effective than the extraction of KCl by cation carrier 1.
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73. Van Esch, J.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281.
74. m,0) and follows from eq 11.
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