Kinetically stable caviplexes in water [16]

Journal of the American Chemical Society

Volumn 121, Issue 48, 1999, Pages 11253-11254

  Haino, Takeharu ^a   Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ADAMANTANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; PARA XYLENE; WATER;

AQUEOUS SOLUTION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; ENANTIOMER; HYDROGEN BOND; LETTER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

EID: 0033537044     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993365w     Document Type: Letter

References (31)

1. (a) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
2. (b) Odashima, K.; Koga, K. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 143-194.
3. (c) Dougherty, D. A. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 195-209.
4. (d) Murakami, Y.; Hayashida, O. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 419-438.
5. Several excellent reviews on the host-guest chemistry of cyclodextrins may be found in: Chem. Rev. 1998, 98, pp 1741-2076.
6. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
7. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
8. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
9. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
10. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
11. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
12. Leading references on water-soluble calixarene-based receptors and cavitands for organic guests: (a) Manabe, O.; Asakura, K.; Nishi, T.; Shinkai, S. Chem. Lett. 1990, 1219-1222. (b) Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, I.; Iwamoto, M. J. Am. Chem. Soc. 1990, 112, 9053-9058. (c) Grote Gansey, M. H. B.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447-5450. (d) Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Chem. Eur. J. 1999, 5, 718-744 and references therein. (e) Bügler, J.; Sommerdijk, N. A. J. M.; Visser, A. J. W. G.; van Hoek, A.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D N. J. Am. Chem. Soc. 1999, 121, 28-33. (f) Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994. Review: Pochini, A.; Ungaro, R. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 103-142.
13. In cryptophanes and hemicarcerands, high kinetic stability of the complexes was achieved in aqueous solution: (a) Collett, A. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 352-355. (b) Yoon, J.; Cram, D. J. Chem. Commun. 1997, 497-498.
14. In cryptophanes and hemicarcerands, high kinetic stability of the complexes was achieved in aqueous solution: (a) Collett, A. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Tarrytown, NY, 1996; Vol. 2, pp 352-355. (b) Yoon, J.; Cram, D. J. Chem. Commun. 1997, 497-498.
15. (a) Cram, D. J. Science 1983, 219, 1177-1183.
16. (b) Cram, D. J.; Cram, J. M. Container Molecules and their Guests; Royal Society of Chemistry: Cambridge, 1994.
17. (c) Rudkevich, D. M.; Rebek, J. Jr. Eur. J. Org. Chem. 1999, 1991-2005.
18. (a) Rudkevich, D. M.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 9911-9912.
19. (b) Rudkevich, D. M.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 12216-12225.
20. (c) Renslo, A. R.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 7459-7460.
21. (d) Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 2600-2602.
22. Detailed experimental procedures will be published elsewhere. See Supporting Information for selected spectral data. Tris(hydroxymethyl)-aminomethane was used in the syntheses of water-soluble calix[4]arenes, see: (a) Grote Gansey, M. H. B.; Steemers, F. J.; Verboom, W.; Reinhoudt, D. N. Synthesis 1997, 643. (b) Steemers, F. J.; Meuris, H. G.; Verboom, W.; Reinhoudt, D. N.; van der Tol, E. B.; Verhoeven, J. W. J. Org. Chem. 1997, 62, 4229-4235.
23. Detailed experimental procedures will be published elsewhere. See Supporting Information for selected spectral data. Tris(hydroxymethyl)-aminomethane was used in the syntheses of water-soluble calix[4]arenes, see: (a) Grote Gansey, M. H. B.; Steemers, F. J.; Verboom, W.; Reinhoudt, D. N. Synthesis 1997, 643. (b) Steemers, F. J.; Meuris, H. G.; Verboom, W.; Reinhoudt, D. N.; van der Tol, E. B.; Verhoeven, J. W. J. Org. Chem. 1997, 62, 4229-4235.
24. 6 (i.e., ∼0.7 ppm upfield of the corresponding signal of 1a in the same solvent).
25. 1H NMR).
26. 1H NMR spectra observed at higher concentrations is most probably due to some nonspecific lipophilic aggregation in aqueous media. Hydrogen bonding amide sites on the periphery of the molecule may also be involved. In addition, some changes in the spectra of 1b were detected upon varying the temperature (5-80°C). See Supporting Information for the details.
27. (11 ) (a) Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 5707-5714.
28. (b) Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765.
29. 1H NMR at millimolar concentrations.
30. For typical examples see: (a) Schneider, H.-J.: Güttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449-6454. (b) Alvarez, J.; Wang, Y.; Gomez-Kaifer, M.; Kaifer, A. Chem. Commun. 1998, 1455-1456.
31. For typical examples see: (a) Schneider, H.-J.: Güttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449-6454. (b) Alvarez, J.; Wang, Y.; Gomez-Kaifer, M.; Kaifer, A. Chem. Commun. 1998, 1455-1456.