Kinetic and thermodynamic analysis of induced-fit molecular recognition between tetraarylporphyrin and ubiquinone analogues

Chemistry - A European Journal

Volumn 4, Issue 7, 1998, Pages 1266-1274

  Hayashi, Takashi ^a,b   Asai, Tomohito ^a   Borgmeier, Frieder M ^a   Hokazono, Hirohisa ^a   Ogoshi, Hisanohu ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c FUKUI NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Atropisomerism; Molecular recognition; Porphyrinoids; Quinones

Indexed keywords

EID: 0031825397     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980710)4:7<1266::AID-CHEM1266>3.0.CO;2-T     Document Type: Article

References (52)

1. D.J. Cram, Angew. Chem. 1988, 100, 1041; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009.
2. D.J. Cram, Angew. Chem. 1988, 100, 1041; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009.
3. a) D.E. Koshland, Jr., Proc. Natl. Acad. Sci. USA 1958, 44, 98;
4. b) D. E. Koshland, Jr., Angew. Chem. 1994, 106, 2468; Angew. Chem. Int. Ed. Engl. 1994, 33, 2375.
5. b) D. E. Koshland, Jr., Angew. Chem. 1994, 106, 2468; Angew. Chem. Int. Ed. Engl. 1994, 33, 2375.
6. a) T. A. Steitz, M. L. Ludwig, F. A. Quiocho, W. N. Lipscomb, J. Biol. Chem. 1967, 242, 4662 ;
7. b) W. S. Bennett, R. Huber, Crit. Rev. Biochem. 1984, 15, 291;
8. c) M. Gerstein, A. M. Lesk, C. Chothia, Biochemistry 1994, 33, 6739.
9. a) C.-W. Chen, H. W. Whitlock, Jr., J. Am. Chem. Soc. 1978, 100, 4921;
10. b) J. Rebek, Jr., B. Askew, M. Killoran, D. Nemeth, F.-T. Lin, J. Am. Chem. Soc. 1987, 109, 2426;
11. c) J. C. Adrian, C. S. Wilcox, J. Am. Chem. Soc. 1989, 111, 8055;
12. d) G. M. Sanders, M. van Dijk, B. M. Machiels, A. van Veldhuizen, J. Org. Chem. 1991, 56, 1301;
13. e) C Vicent, S. C. Hirst, F. Garcia-Tellado, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 5466;
14. f) R. P. Sijbesma, R. J. M. Nolle, J. Am. Chem. Soc. 1991, 113, 6695;
15. g) J. C. Adrian, Jr., C. S. Wilcox, J. Am. Chem. Soc. 1992, 114, 1398;
16. h) R. Güther, M. Nieger, F. Vögtle, Angew. Chem. 1993, 105, 647; Angew. Chem. Int. Ed. Engl. 1993, 32, 601;
17. h) R. Güther, M. Nieger, F. Vögtle, Angew. Chem. 1993, 105, 647; Angew. Chem. Int. Ed. Engl. 1993, 32, 601;
18. i) M. M. Conn, G. Deslongchamps, J. de Mendoza, J. Rebek, Jr., J. Am. Chem. Soc. 1993, 115, 3548;
19. j) M. Fujita, F. Ibukuro, H. Hagihara, K. Ogura, Nature 1994, 367, 720;
20. k) D. V. Stynes, Inorg. Chem, 1994, 33, 5022;
21. l) F. Würthner, J. Rebek, Jr., Angew. Chem. 1995, 107, 503; Angew. Chem. Int. Ed. Engt. 1995, 34, 446;
22. l) F. Würthner, J. Rebek, Jr., Angew. Chem. 1995, 107, 503; Angew. Chem. Int. Ed. Engt. 1995, 34, 446;
23. m) M. Fujita, S. Nagao, K. Ogura, J. Am. Chem. Soc. 1995, 117, 1649;
24. n) H. L. Anderson, S. Andersen, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 2231;
25. o) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487;
26. p) I. Vernik, D. V. Stynes, Inorg. Chem. 1996, 35, 6210;
27. q) A. V. Eliseev, M. I. Nelen, J. Am. Chem. Soc. 1997, 119, 1147;
28. r) M. A. Houghton, A. Biiyk, M. M. Harding, P. Turner, T. W. Hambley, J. Chem. Soc. Dalton Trans. 1997, 2725.
29. Recently, we have reported that meso-tetrakis(2-hydroxynaphthyl)porphyrin (2) is a suitable ubiquinone receptor. The atropisomerization of 2 was not detected even in boiling toluene. T. Hayashi, T. Miyahara, N. Koide, Y. Kato, H. Masuda, H. Ogoshi, J. Am. Chem. Soc. 1997, 119, 7281.
30. T. Hayashi, T. Asai, H. Hokazono, H. Ogoshi, J. Am. Chem. Soc. 1993, 115, 12210.
31. L. K. Gottwald, E. F. Ullman, Tetrahedron Lett. 1969, 3071.
32. C. M. Elliott, Anal. Chem. 1980, 52, 666.
33. J. Lindsey, J. Org. Chem. 1980, 45, 5215.
34. Several groups have described a thermal shift in the equilibrium of atropisomers at high temperatures. See for example: a) N. Nishino, K. Kobata, H. Mihara, T. Fujimoto, Chem. Lett. 1992, 1991; b) E. Rose, M. Quelquejeu, C. Pochet, N. Julien, A. Kossanyi, L. J. Hamon. Org. Chem. 1993, 58, 5030; c) J. Setsune, M. Hashimoto, J. Chem. Soc. Chem. Commun. 1994, 657; d) E. Rose, A. Cardon-Pilotaz, M. Quelquejeu, N. Bernard, A. Kossanyi, B. Desmazières, J. Org. Chem. 1995, 60, 3919.
35. Several groups have described a thermal shift in the equilibrium of atropisomers at high temperatures. See for example: a) N. Nishino, K. Kobata, H. Mihara, T. Fujimoto, Chem. Lett. 1992, 1991; b) E. Rose, M. Quelquejeu, C. Pochet, N. Julien, A. Kossanyi, L. J. Hamon. Org. Chem. 1993, 58, 5030; c) J. Setsune, M. Hashimoto, J. Chem. Soc. Chem. Commun. 1994, 657; d) E. Rose, A. Cardon-Pilotaz, M. Quelquejeu, N. Bernard, A. Kossanyi, B. Desmazières, J. Org. Chem. 1995, 60, 3919.
36. Several groups have described a thermal shift in the equilibrium of atropisomers at high temperatures. See for example: a) N. Nishino, K. Kobata, H. Mihara, T. Fujimoto, Chem. Lett. 1992, 1991; b) E. Rose, M. Quelquejeu, C. Pochet, N. Julien, A. Kossanyi, L. J. Hamon. Org. Chem. 1993, 58, 5030; c) J. Setsune, M. Hashimoto, J. Chem. Soc. Chem. Commun. 1994, 657; d) E. Rose, A. Cardon-Pilotaz, M. Quelquejeu, N. Bernard, A. Kossanyi, B. Desmazières, J. Org. Chem. 1995, 60, 3919.
37. Several groups have described a thermal shift in the equilibrium of atropisomers at high temperatures. See for example: a) N. Nishino, K. Kobata, H. Mihara, T. Fujimoto, Chem. Lett. 1992, 1991; b) E. Rose, M. Quelquejeu, C. Pochet, N. Julien, A. Kossanyi, L. J. Hamon. Org. Chem. 1993, 58, 5030; c) J. Setsune, M. Hashimoto, J. Chem. Soc. Chem. Commun. 1994, 657; d) E. Rose, A. Cardon-Pilotaz, M. Quelquejeu, N. Bernard, A. Kossanyi, B. Desmazières, J. Org. Chem. 1995, 60, 3919.
38. Y. Kuroda, A. Kawashima, Y. Hayashi, H. Ogoshi, J. Am. Chem. Soc. 1997, 119, 4929.
39. M. Kumada, K. Tamao, K. Sumitani, Org. Synth. 1978, 58, 127.
40. [6] However, ethanol can act as a competitive inhibitor in the formation of hydrogen-bonded complexes. In this paper, we used chloroform containing 2-methyl-2-butene as a stabilizer to obtain the thermodynamic parameters.
41. T. Hayashi, T. Miyahara, Y. Aoyama, M. Kobayashi, H. Ogoshi, Pure Appl. Chem. 1994, 66, 797.
42. The downfield shift of the OH protons shown in Figure 4-IIb depends on the degree of hydrogen bonding of the OH groups.
43. M. J. Crossley, L. D. Field, A. J. Forster, M. M. Harding, S. Sternhell, J. Am. Chem. Soc. 1987, 109, 341.
44. αααβ-Q])- re-spectively, since the exchange process between the free and complexed host molecule is fast on the NMR time scale.
45. αααβ-Q without intermediate dissociation to porphyrin and quinone is assumed in this system, the simulated curves for the relative amounts of each atropisomer cannot be reconciled with the kinetic data shown in Figure 8 and 11.
46. J. L. Hoard, in Porphyrins and Melalloporphyrins, (Ed.: K. M. Smith), Eisevier, Amsterdam, 1975, p. 317.
47. R. G. Alden, B. A. Crawford, R. Doolen, M. R. Ondrias, J. A. Shelnutt, J. Am. Chem. Soc. 1989, 111, 2070.
48. R. A. Freitag, D. G. Whitten, J. Phys. Chem. 1983, 87, 3918.
49. H. Orita, M. Shimizu, T. Hayakawa, K. Takehira, Bull. Chem. Soc. Jpn. 1989, 62, 1652.
50. M. H. Akhtar, A. Begleiter, D. Johnson, W. Lown, L. McLaughlin, S.-K. Sim, Can. J. Chem. 1975, 53. 2891.
51. α carbons of the four pyrrole rings were not detected, owing to the broadening derived from N-H tautomerism.
52. Several singlet peaks appear at the same position for each phenyl and pyrrole carbon, owing to the presence of a mixture of four atropisomers.