Lower rim-upper rim hydrogen-bonded adducts of calix[4]arenes

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4282-4288

  Vreekamp, Remko H ^a   Verboom, Willem ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000398232     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9603082     Document Type: Article

References (57)

1. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304.
2. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312.
3. Whitesides, G. M.; Simanek, E. K.; Mathias, J. P.; Seto, C. T.; Donovan, N. C.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37.
4. Lindsey, J. S. New J. Chem. 1991, 15, 153.
5. Ozin, G. A. Adv. Mat. 1992, 4, 612.
6. (a) Gutsche, C. D. Calixarenes; Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989; Vol. 1.
7. (b) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer Academic Press: Dordrecht, 1991.
8. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
9. For a few recent examples see: (a) Cobben, P. L. H. M.; Egberink, R. J. M.; Borner, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 10573. (b) Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1505. (c) Arnaud-Neu, F.; Barrett, G.; Harris, S. J.; Owens, M.; McKervey, M. A.; Schwing-Weill, M.-J.; Schwinte, P. Inorg. Chem. 1993, 32, 2644.
10. For a few recent examples see: (a) Cobben, P. L. H. M.; Egberink, R. J. M.; Borner, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 10573. (b) Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1505. (c) Arnaud-Neu, F.; Barrett, G.; Harris, S. J.; Owens, M.; McKervey, M. A.; Schwing-Weill, M.-J.; Schwinte, P. Inorg. Chem. 1993, 32, 2644.
11. For a few recent examples see: (a) Cobben, P. L. H. M.; Egberink, R. J. M.; Borner, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 10573. (b) Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1505. (c) Arnaud-Neu, F.; Barrett, G.; Harris, S. J.; Owens, M.; McKervey, M. A.; Schwing-Weill, M.-J.; Schwinte, P. Inorg. Chem. 1993, 32, 2644.
12. For a few recent examples see: (a) Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. (b) Beer, P. D.; Chen, Z.; Goulden, A. J.; Graydon, A.; Stokes, S. E.; Wear, T. J. Chem. Soc., Chem. Commun. 1993, 1834.
13. For a few recent examples see: (a) Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. (b) Beer, P. D.; Chen, Z.; Goulden, A. J.; Graydon, A.; Stokes, S. E.; Wear, T. J. Chem. Soc., Chem. Commun. 1993, 1834.
14. (a) van Loon, J.-D.; Heida, J. F.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1992, 33, 353.
15. (b) Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527.
16. (c) Murakami, H.; Shinkai, S. Tetrahedron Lett. 1993, 34, 4237.
17. (d) Murakami, H.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1993, 1533.
18. (e) Timmerman, P.; Brinks, E. A.; Verboom, W.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 417.
19. (a) Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215.
20. (b) Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1330.
21. (c) Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301.
22. (d) Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85.
23. (e) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43.
24. Fujimoto, K.; Shinkai, S. Tetrahedron Lett. 1994, 35, 2915.
25. (a) van Loon, J.-D.; Janssen, R. G.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1992, 33, 5125.
26. (b) van Loon, J.-D. Ph.D. Thesis, University of Twente, 1992.
27. Hammes, G. G.; Park, A. C. J. Am. Chem. Soc. 1969, 91, 956.
28. All association constants given are in chloroform at 298 K unless stated otherwise.
29. Koh, K.; Araki, K.; Shinkai, S. Tetrahedron Lett. 1994, 35, 8255.
30. Arduini, A.; Fabbi, M.; Mantovani, M.; Mirone, L.; Pochini, A.; Secchi, A.; Ungaro, R. J. Org. Chem. 1995, 60, 1454.
31. Recently Shinkai et al. reported the formation of hydrogen-bonded complexes/structures comprising calix[4]arenes substituted with diaminopyridine moieties at the lower rim and simple barbituric acid derivatives: Lhotak, P.; Shinkai, S. Tetrahedron Lett. 1995, 36, 4829.
32. This interaction has been used in the design of receptors for amines by Rebek et al.: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. The interaction is also used to stabilize liquid crystallinity in polymers or to introduce ferroelectricity. See, for instance: Wilson, L. M. Macromol. 1994, 27, 6683. Kumar, U.; Fréchet, J. M. J.; Kato, T.; Ujiie, S.; Timura, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1531. The same interaction was used by Shinkai et al. in the construction of the upper rim hydrogen-bonded calix[4]arene duplexes mentioned above. Further, interesting solid state structures were obtained by mixing isophthalic acids with pyrimidine or pyrazine: Valiyaveetil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097.
33. This interaction has been used in the design of receptors for amines by Rebek et al.: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. The interaction is also used to stabilize liquid crystallinity in polymers or to introduce ferroelectricity. See, for instance: Wilson, L. M. Macromol. 1994, 27, 6683. Kumar, U.; Fréchet, J. M. J.; Kato, T.; Ujiie, S.; Timura, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1531. The same interaction was used by Shinkai et al. in the construction of the upper rim hydrogen-bonded calix[4]arene duplexes mentioned above. Further, interesting solid state structures were obtained by mixing isophthalic acids with pyrimidine or pyrazine: Valiyaveetil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097.
34. This interaction has been used in the design of receptors for amines by Rebek et al.: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. The interaction is also used to stabilize liquid crystallinity in polymers or to introduce ferroelectricity. See, for instance: Wilson, L. M. Macromol. 1994, 27, 6683. Kumar, U.; Fréchet, J. M. J.; Kato, T.; Ujiie, S.; Timura, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1531. The same interaction was used by Shinkai et al. in the construction of the upper rim hydrogen-bonded calix[4]arene duplexes mentioned above. Further, interesting solid state structures were obtained by mixing isophthalic acids with pyrimidine or pyrazine: Valiyaveetil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097.
35. This interaction has been used in the design of receptors for amines by Rebek et al.: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. The interaction is also used to stabilize liquid crystallinity in polymers or to introduce ferroelectricity. See, for instance: Wilson, L. M. Macromol. 1994, 27, 6683. Kumar, U.; Fréchet, J. M. J.; Kato, T.; Ujiie, S.; Timura, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1531. The same interaction was used by Shinkai et al. in the construction of the upper rim hydrogen-bonded calix[4]arene duplexes mentioned above. Further, interesting solid state structures were obtained by mixing isophthalic acids with pyrimidine or pyrazine: Valiyaveetil, S.; Enkelmann, V.; Müllen, K. J. Chem. Soc., Chem. Commun. 1994, 2097.
36. (a) Arduini, A.; Manfredi, G.; Pochini, A.; Sicuri, A. R.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1991, 936.
37. (b) Arduini, A.; Fanni, S.; Manfredi, G.; Pochini, A.; Ungaro, R.; Sicuri, A. R.; Ugozzoli, F. J. Org. Chem. 1995, 60, 1448.
38. van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.
39. The route via the tetraformyl derivative has the advantage over the procedure described by Regen et al. of being clean and producing the tetracarboxylic acid in good yield after very simple purification, especially on a larger scale. Conner, M.; Janout, V.; Regen, S. L. J. Org. Chem. 1992, 57, 3744.
40. Pappalardo, S.; Giunta, L.; Foti, M.; Ferguson, G.; Gallager, J. F.; Kaitner, B. J. Org. Chem. 1992, 57, 2611.
41. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325.
42. Dicarboxylic acid 2 is quite soluble in chloroform and is assumed to be present as a strongly hydrogen-bonded dimer in apolar solvents like chloroform, since such behavior was established recently for a closely related compound: (a) Arduini, A.; Fabbi, M.; Mantovani, M.; Mirone, L.; Pochini, A.; Secchi, A.; Ungaro, R. J. Org. Chem. 1995, 60, 1454.
43. Wilcox, C. S. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH Publishers: Weinheim, 1991.
44. d (a) Dega-Szafran, Z.; Grech, E.; Naskret-Barciszewska, M. Z.; Szafran, M. J. Chem. Soc., Perkin Trans. 2 1975, 250. (b) Chihara, H.; Nakamura, N. Bull. Chem. Soc. Jpn. 1971, 44, 1980. (c) Barrow, G. M. J. Am. Chem. Soc. 1956, 78, 5802. (d) Johnson, S. L.; Rumon, K. A. J. Phys. Chem. 1965, 69, 74.
45. d (a) Dega-Szafran, Z.; Grech, E.; Naskret-Barciszewska, M. Z.; Szafran, M. J. Chem. Soc., Perkin Trans. 2 1975, 250. (b) Chihara, H.; Nakamura, N. Bull. Chem. Soc. Jpn. 1971, 44, 1980. (c) Barrow, G. M. J. Am. Chem. Soc. 1956, 78, 5802. (d) Johnson, S. L.; Rumon, K. A. J. Phys. Chem. 1965, 69, 74.
46. d (a) Dega-Szafran, Z.; Grech, E.; Naskret-Barciszewska, M. Z.; Szafran, M. J. Chem. Soc., Perkin Trans. 2 1975, 250. (b) Chihara, H.; Nakamura, N. Bull. Chem. Soc. Jpn. 1971, 44, 1980. (c) Barrow, G. M. J. Am. Chem. Soc. 1956, 78, 5802. (d) Johnson, S. L.; Rumon, K. A. J. Phys. Chem. 1965, 69, 74.
47. d (a) Dega-Szafran, Z.; Grech, E.; Naskret-Barciszewska, M. Z.; Szafran, M. J. Chem. Soc., Perkin Trans. 2 1975, 250. (b) Chihara, H.; Nakamura, N. Bull. Chem. Soc. Jpn. 1971, 44, 1980. (c) Barrow, G. M. J. Am. Chem. Soc. 1956, 78, 5802. (d) Johnson, S. L.; Rumon, K. A. J. Phys. Chem. 1965, 69, 74.
48. a of 0.90 and a maximum value of 1.72. Since both of these values are < 2 it may be assumed that any interaction between these acids and bases will be of a hydrogen-bonded nature, with negligible proton transfer.
49. a of 0.90 and a maximum value of 1.72. Since both of these values are < 2 it may be assumed that any interaction between these acids and bases will be of a hydrogen-bonded nature, with negligible proton transfer.
50. a of 0.90 and a maximum value of 1.72. Since both of these values are < 2 it may be assumed that any interaction between these acids and bases will be of a hydrogen-bonded nature, with negligible proton transfer.
51. a of 0.90 and a maximum value of 1.72. Since both of these values are < 2 it may be assumed that any interaction between these acids and bases will be of a hydrogen-bonded nature, with negligible proton transfer.
52. Horman, I.; Dreux, B. Helv. Chim. Acta 1984, 67, 754.
53. The possible self-association of the components has not been taken into account since in the case of tetracarboxylic acid 5 this could not be determined on account of its very low solubility in chloroform. The estimated error in the K values is about 10%.
54. Qualitatively, the stronger interaction is also indicated by the ease of which the initial suspensions of the 1:1 mixtures become clear solutions.
55. Conner, M.; Janout, V.; Regen, S. L. J. Am. Chem. Soc. 1991, 113, 9670.
56. 2v symmetry.
57. -1.