Isomeric 2,6-pyridino-cryptands based on dibenzo-24-crown-8

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3381-3393

  Gibson, Harry W ^a   Wang, Hong ^a,c   Slebodnick, Carla ^a   Merola, Joseph ^a   Kassel, W Scott ^b,d   Rheingold, Arnold L ^b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c ALKERMES INC   (United States)

^d VILLANOVA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYPTANDS; CRYSTAL STRUCTURES; DIBENZO-24-CROWN-8; PSEUDOROTAXANES;

ADDITION REACTIONS; CARBOXYLIC ACIDS; CROWN ETHERS; ISOMERS; SYNTHESIS (CHEMICAL);

PYRIDINE;

AMMONIUM FLUORIDE; AMMONIUM HEXAFLUOROPHOSPHATE; BENZENE DERIVATIVE; CROWN ETHER DERIVATIVE; CRYPTAND; DIBENZO 24 CROWN 8; DIPICOLINIC ACID; FLUOROPHOSPHATE; LIGAND; N,N' BIS(BETA HYDROXYETHYL) 4,4' BIPYRIDINIUM BIS(HEXAFLUOROPHOSPHATE); PARAQUAT; POLYCYCLIC HYDROCARBON; POTASSIUM ION; PSEUDOROTAXANE; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ISOMER; SYNTHESIS;

EID: 34247618149     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070030l     Document Type: Article

References (71)

1. Ball, P. Nanotechnology 2002, 13, R15-R28.
2. Kinbara, K.; Aida, T. Chem. Rev. 2005, 105, 1377-1400.
3. Rapenne, G. Org. Biomol. Chem. 2005, 3, 1165-1169.
4. Jansen, R. J.; de Gelder, R.; Rowan, A. E.; Scheeren, H. W.; Nolte, R. J. M. J. Org. Chem. 2001, 66, 2643-2653.
5. Pittelkow, M.; Christensen, J. B.; Meijer, E. W. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3792-3799.
6. Arunkumar, E.; Chithra, P.; Ajayaghosh, A. J. Am. Chem. Soc. 2004, 126, 6590-6598.
7. Inokuma, S.; Funaki, T.; Kondo, S.; Nishimura, J. Tetrahedron 2004, 60, 2043-2050.
8. Rudkevich, D. M.; Leontiev, A. V. Aust. J. Chem. 2004, 57, 713-722.
9. Liu, Y.; Song, Y.; Chen, Y.; Yang, Z.-X.; Ding, F. J. Phys. Chem. B 2005, 109, 10717-10726.
10. Rudkevich, D. M.; Kang, Y.; Leontiev, A. V.; Organo, V. G.; Zyryanov, G. V. Supramol. Chem. 2005, 17, 93-99.
11. (a) Yamaguchi, N.; Nagvekar, D. S.; Gibson, H. W. Angew. Chem., Int. Ed. 1998, 37, 2361-2364.
12. (b) Yamaguchi, N.; Gibson, H. W. Angew. Chem., Int. Ed. 1999, 38, 143-147.
13. (c) Gibson, H. W.; Yamaguchi, N.; Jones, J. W. J. Am. Chem. Soc. 2003, 125, 3522-3533.
14. (d) Huang, F.; Gibson, H. W. Chem. Commun. 2005, 1696-1698.
15. (e) Huang, F.; Nagvekar, D. S.; Zhou, Z.; Gibson, H. W. Macromolecules 2007, 40, in press.
16. Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604.
17. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495-2496.
18. Pederson, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036.
19. Pedersen, C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1021-1027.
20. Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J.; Sen, D. Chem. Rev. 1985, 85, 271-339.
21. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1991, 91, 1721-2085.
22. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-86.
23. Gokel, G. W.; Abel, E. Comprehensive Supramolecular Chemistry; Gokel, G., Ed.; Pergamon: New York, 1996: Vol. 1, pp 511-535.
24. Maverick, E.; Cram, D. J. Comprehensive Supramolecular Chemistry; Gokel, G., Ed.; Pergamon: New York, 1996; Vol. 1, pp 213-243.
25. Xue, G.; Savage, P. B.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. Adv. Supramol. Chem. 2000, 7, 99-137.
26. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723-2750.
27. Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P., Dietrich-Buchecker, C. O., Eds.; Wiley-VCH: Weinheim, Germany. 1999.
28. Mahan, E.; Gibson, H. W. In Cyclic Polymers, 2nd ed.; Semlyen, J. A., Ed.; Kluwer Publishers: Dordrecht, The Netherlands. 2000; pp 415-560.
29. Fyfe, M. C. T.; Stoddart, J. F. Adv. Supramol. Chem. 1999, 5, 1-53.
30. Cantrill, S. J.; Pease, A. R.; Stoddart, J. F. J. Chem. Soc. Dalton Trans. 2000, 3715-3734.
31. Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200-202, 5-52.
32. Takata, T.; Kihara, N. Rev. Heteroatom Chem. 2000, 22, 197-218.
33. Panova, I. G.; Topchieva, I. N. Russ. Chem. Rev. 2001, 70, 23-44.
34. Kim, K. Chem. Soc. Rev. 2002, 31, 96-107.
35. Felder, T.; Schalley, C. A. Highlights Bioorg. Chem. 2004, 526-539.
36. Flood, A. H.; Ramirez, R. J. A.; Deng, W.-Q.; Muller, R. P.; Goddard, W. A., III; Stoddart, J. F. Aust. J. Chem. 2004, 57, 301-322.
37. Sauvage, J.-P. Chem. Commun. 2005, 1507-1510.
38. Huang, F.; Gibson, H. W. Prog. Polym. Sci. 2005, 30, 982-1018.
39. A cryptand is defined (IUPAC Compendium of Chemical Terminology, 2nd ed.; 1997) as "a molecular entity comprising a cyclic or polycyclic assembly of binding sites that contains three or more binding sites held together by covalent bonds, and which defines a molecular cavity in such a way as to bind (and thus 'hide' in the cavity) another molecular entity, the guest (a cation, an anion or a neutral species), more strongly than do the separate parts of the assembly (at the same total concentration of binding sites). - The term is usually restricted to bicyclic or oligocyclic molecular entities."
40. Simmons, H. E.; Park, C. H. J. Am. Chem. Soc. 1968, 90, 2428.
41. Simmons, H. E.; Park, C. H. J. Am. Chem. Soc., 1968, 90, 2429.
42. Simmons, H. E.; Park, C. H. J. Am. Chem. Soc. 1968, 90, 2431.
43. Parsons, D. G. J. Chem. Soc. Perkin Trans. I 1978, 451.
44. Dietrich, B. In Comprehensive Supramolecular Chemistry:, Gokel, G., Ed.; Pergamon Press: New York, 1996; Vol. 1, pp 153-211.
45. Jones, J. W.; Zakharov, L. N.; Rheingold, A. L.; Gibson, H. W. J. Am. Chem. Soc. 2002, 124, 13378-13379.
46. Huang, F.; Zhakarov, L.; Rheingold, A. L.; Jones, J. W.; Gibson, H. W. J. Chem. Soc. Chem. Commun. 2003, 2122-2123.
47. Huang, F.; Guzei, I. A.; Jones, J. W.; Gibson, H. W. Chem. Commun. 2005, 1693-1695.
48. (a) Bryant, W. S.; Jones, J. W.; Mason, P. E.; Guzei, I. A.; Rheingold, A. L.; Nagvekar, D. S.; Gibson, H. W. Org. Lett. 1999, 1, 1001-1004.
49. (b) Huang, F.; Switek, K. A.; Zakharov, L. N.; Fronczek, F.; Slebodnick C.; Lam, M.; Golen, J. A.; Bryant, W. S.; Mason, P.; Ashraf-Khorassani, M; Rheingold, A. L.; Gibson, H. W. J. Org. Chem. 2005, 70, 3231-3241.
50. Gibson, H. W.; Wang, H.; Bonrad, K.; Jones, J. W.; Slebodnick, C.; Habenicht, B.; Lobue, P. Org. Biomol. Chem. 2005, 3, 2114-2121.
51. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95-102.
52. Dietrich, B.; Viout, P.; Lehn J. M. Macrocyclic Chemistry; VCH: New York, 1993.
53. Weber, G. Molecular Biophysics; Pullman, B., Weissbluth, M., Eds.; Academic Press: New York, 1965; pp 369-397.
54. Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Lehn, J.-M., Eds.; Pergamon: New York, 1996; Vol. 8, pp 436-439.
55. (a) Jones, J. W.; Gibson, H. W. J. Am. Chem. Soc. 2003, 125, 7001-7004.
56. (b) Huang, F.; Jones, J. W.; Gibson, H. W. J. Am. Chem. Soc. 2003, 125, 14458-14464.
57. Takeda, Y. Bull. Chem. Soc. Jpn. 1983, 56, 3600-3602.
58. Takeda, Y.; Kudo, Y.; Fujiwara, S. Bull. Chem. Soc. Jpn., 1985, 58, 1315-1316.
59. Tawarah, K. M.; Mizyed, S. A. J. Solution Chem. 1989, 18, 387-401.
60. Chantooni, M. K., Jr.; Roland, G.; Kolthoff, I. M. J. Solution Chem. 1988, 17, 175-189.
61. Frensdorff, H. K. J. Am. Chem. Soc. 1971, 93, 600-606.
62. Yen, M.-L.; Li, W.-S.; Lai, C.-C.; Chao, I.; Chiu, S.-H. Org. Lett. 2006, 8, 3223-3226.
63. De Boer, J. A. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1985, 107, 5347-51.
64. Cram, D. J. Science 1988, 240, 760-767.
65. Ozbey, S.; Kaynak, F. B.; Togrul, M.; Demirel, N.; Hosgoren, H. Z. Kristallogr. 2003, 218, 381-384.
66. Gibson, H. W.; Nagvekar, D. S. Can. J. Chem. 1997, 75, 1375-1384.
67. Shen, Y. X.; Engen, P. T.; Berg, M. A. G.; Merola, J. S.; Gibson, H. W. Macromolecules 1992, 25, 2786-2787.
68. CrysAlis, v1.171; Oxford Diffraction: Wroclaw, Poland, 2004.
69. SMART, Bruker Analytical X-Ray Systems, Inc.: Madison, WI, 2001.
70. Sheldrick, G. M. SHELXTL NT, ver. 6.12; Bruker Analytical X-ray Systems, Inc.: Madison, WI, 2001.
71. Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13.