Molecular recognition: The demonstration of 1,3-bis[(pyrid-2-ylamino)carbonyl]adamantane as an exceptionally versatile assembler of one-dimensional motifs

Journal of the American Chemical Society

Volumn 119, Issue 12, 1997, Pages 2777-2783

  Karle, Isabella L ^a   Ranganathan, Darshan ^b   Haridas, V ^b  

^a NAVAL RESEARCH LABORATORY   (United States)

^b REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CRYSTALLIZATION; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; X RAY CRYSTALLOGRAPHY;

EID: 0030891239     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9623121     Document Type: Article

References (46)

1. For recent updates in self-assembly, see: (a) Lehn, J.-M. Supramolecular chemistry: Concepts and perspectives; VCH: Weinheim, 1995. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (c) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (d) Whitesides, G. M.; McDonald, J. C. Chem. Rev 1994, 94, 2383 (e) Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
2. For recent updates in self-assembly, see: (a) Lehn, J.-M. Supramolecular chemistry: Concepts and perspectives; VCH: Weinheim, 1995. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (c) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (d) Whitesides, G. M.; McDonald, J. C. Chem. Rev 1994, 94, 2383 (e) Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
3. For recent updates in self-assembly, see: (a) Lehn, J.-M. Supramolecular chemistry: Concepts and perspectives; VCH: Weinheim, 1995. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (c) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (d) Whitesides, G. M.; McDonald, J. C. Chem. Rev 1994, 94, 2383 (e) Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
4. For recent updates in self-assembly, see: (a) Lehn, J.-M. Supramolecular chemistry: Concepts and perspectives; VCH: Weinheim, 1995. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (c) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (d) Whitesides, G. M.; McDonald, J. C. Chem. Rev 1994, 94, 2383 (e) Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
5. For recent updates in self-assembly, see: (a) Lehn, J.-M. Supramolecular chemistry: Concepts and perspectives; VCH: Weinheim, 1995. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (c) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (d) Whitesides, G. M.; McDonald, J. C. Chem. Rev 1994, 94, 2383 (e) Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
6. (a) Kane, J. J.; Liao, R.-F.; Lauher, J. W.; Fowler, F. W. J. Am. Chem. Soc. 1995, 117, 12003.
7. (b) Goodman, M. S.; Hamilton, A. D.; Weiss, J. J. Am. Chem. Soc. 1995, 117, 8447.
8. (c) Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630.
9. (d) Russel, V. A.; Etter, M. C.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 1941.
10. (e) Stumpf, H. O.; Pei, Y.; Kahn, O.; Sletten, J.; Renard, J. P. J. Am. Chem. Soc. 1993, 115, 6738 and references cited therein.
11. (f) Yang, J.; Fan, E.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 5314.
12. (g) Chang, Y. L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991.
13. (h) Lauher, J. W.; Chang, Y.-L.; Fowler, F. W. Mol. Cryst. Liq. Cryst. 1992, 211, 99.
14. (i) Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627.
15. (j) Hollingsworth, M. D.; Santansiero, B. D.; Oumar-Mahamat, H.; Nichols, C. J. Chem. Mater. 1991, 3, 23.
16. (k) Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265.
17. (l) Di Salvo, F. J. Science 1990, 247, 649.
18. (m) Desiraju, G. R. Crystal engineering: The design of organic solids; Elsevier: New York, 1989.
19. (n) Ducharme, Y.; Wuest, J. D. J. Org. Chem. 1988, 53, 5787.
20. (a) Etter, M. C.; Reutzel, S. M. J. Am. Chem. Soc. 1991, 113, 2586. Etter, M. C. Acc. Chem. Res. 1990, 23, 120. Etter, M. C.; Lipkowska, Z. U.; Ebrahini, M. Z.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415.
21. (a) Etter, M. C.; Reutzel, S. M. J. Am. Chem. Soc. 1991, 113, 2586. Etter, M. C. Acc. Chem. Res. 1990, 23, 120. Etter, M. C.; Lipkowska, Z. U.; Ebrahini, M. Z.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415.
22. (a) Etter, M. C.; Reutzel, S. M. J. Am. Chem. Soc. 1991, 113, 2586. Etter, M. C. Acc. Chem. Res. 1990, 23, 120. Etter, M. C.; Lipkowska, Z. U.; Ebrahini, M. Z.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415.
23. (b) Another hydrogen bonding functionality that is gaining increasing importance in supramolecular chemistry is the carboxylic group (Rebek, J., Jr., Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. Nowick, J. S.; Ballester, P.; Ebmeyer, F. Rebek, J. Jr., J. Am. Chem. Soc. 1990, 112, 8902. Chang, Y.-L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991. Yang, J.; Marendaz, J.-L.; Geib, S. J.; Hamilton, A. D. Tetrahedron Lett. 1994, 35, 3665. Also see ref 1).
24. (b) Another hydrogen bonding functionality that is gaining increasing importance in supramolecular chemistry is the carboxylic group (Rebek, J., Jr., Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. Nowick, J. S.; Ballester, P.; Ebmeyer, F. Rebek, J. Jr., J. Am. Chem. Soc. 1990, 112, 8902. Chang, Y.-L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991. Yang, J.; Marendaz, J.-L.; Geib, S. J.; Hamilton, A. D. Tetrahedron Lett. 1994, 35, 3665. Also see ref 1).
25. (b) Another hydrogen bonding functionality that is gaining increasing importance in supramolecular chemistry is the carboxylic group (Rebek, J., Jr., Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. Nowick, J. S.; Ballester, P.; Ebmeyer, F. Rebek, J. Jr., J. Am. Chem. Soc. 1990, 112, 8902. Chang, Y.-L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991. Yang, J.; Marendaz, J.-L.; Geib, S. J.; Hamilton, A. D. Tetrahedron Lett. 1994, 35, 3665. Also see ref 1).
26. (b) Another hydrogen bonding functionality that is gaining increasing importance in supramolecular chemistry is the carboxylic group (Rebek, J., Jr., Nemeth, D.; Ballester, P.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 3474. Nowick, J. S.; Ballester, P.; Ebmeyer, F. Rebek, J. Jr., J. Am. Chem. Soc. 1990, 112, 8902. Chang, Y.-L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991. Yang, J.; Marendaz, J.-L.; Geib, S. J.; Hamilton, A. D. Tetrahedron Lett. 1994, 35, 3665. Also see ref 1).
27. The promise of the 2-aminopyridine group as a -COOH binding pocket was first demonstrated by Etter et al. (Etter, M. C.; Adsmond, D. A. J. Chem. Soc., Chem. Commun. 1990, 589) in the formation of hydrogenbonded infinite ribbons in 1:1 molecular complex of 2-aminopyrimidine and succinic acid. Subsequently, this unit has been extensively used by Hamilton and co-workers (Garcia-Tellado.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265) in the design of dicarboxylic acid receptors by a common strategy that involved linking the two aminopyridine groups through a rigid aromatic spacer. A variety of aromatic spacers ranging from simple phenyl to more complex, naphthyl, biphenyl, and terphenyl units were used to create cavities of different sizes for accommodating dicarboxylic acids of varied lengths. In cases where the length of the dicarboxylic acid did not correspond to the cavity size, an alternait mode of binding was observed in the form of infinite ribbons, with each receptor molecule binding to two different molecules of dicarboxylic acid, one above and the other below the cavity resulting in extended structures ( Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119).
28. The promise of the 2-aminopyridine group as a -COOH binding pocket was first demonstrated by Etter et al. (Etter, M. C.; Adsmond, D. A. J. Chem. Soc., Chem. Commun. 1990, 589) in the formation of hydrogenbonded infinite ribbons in 1:1 molecular complex of 2-aminopyrimidine and succinic acid. Subsequently, this unit has been extensively used by Hamilton and co-workers (Garcia-Tellado.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265) in the design of dicarboxylic acid receptors by a common strategy that involved linking the two aminopyridine groups through a rigid aromatic spacer. A variety of aromatic spacers ranging from simple phenyl to more complex, naphthyl, biphenyl, and terphenyl units were used to create cavities of different sizes for accommodating dicarboxylic acids of varied lengths. In cases where the length of the dicarboxylic acid did not correspond to the cavity size, an alternait mode of binding was observed in the form of infinite ribbons, with each receptor molecule binding to two different molecules of dicarboxylic acid, one above and the other below the cavity resulting in extended structures ( Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119).
29. The promise of the 2-aminopyridine group as a -COOH binding pocket was first demonstrated by Etter et al. (Etter, M. C.; Adsmond, D. A. J. Chem. Soc., Chem. Commun. 1990, 589) in the formation of hydrogenbonded infinite ribbons in 1:1 molecular complex of 2-aminopyrimidine and succinic acid. Subsequently, this unit has been extensively used by Hamilton and co-workers (Garcia-Tellado.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265) in the design of dicarboxylic acid receptors by a common strategy that involved linking the two aminopyridine groups through a rigid aromatic spacer. A variety of aromatic spacers ranging from simple phenyl to more complex, naphthyl, biphenyl, and terphenyl units were used to create cavities of different sizes for accommodating dicarboxylic acids of varied lengths. In cases where the length of the dicarboxylic acid did not correspond to the cavity size, an alternait mode of binding was observed in the form of infinite ribbons, with each receptor molecule binding to two different molecules of dicarboxylic acid, one above and the other below the cavity resulting in extended structures ( Geib, S. J.; Vincent, C.; Fan, E.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 119).
30. The syn-syn, syn-anti, and anti-anti terms refer, respectively, to the conformation with the 2-aminopyridine subunits pointing into the center, one inside and the other outside, and both outside the cavity.
31. a value of ∼5 between the acid and aminopyridine, indicative of the possibility of a partial proton transfer from the carboxylic -OH group.
32. Johnson, S. L.; Rumon, K. A. J. Phys. Chem. 1965, 69, 74.
33. a -10) shows the expected FT-IR characteristic of an ionic complex (Supporting Information).
34. -OH bands) studies supports at least a partial proton transfer.
35. 3 (spectra located in the Supporting Information), all attempts to crystallize them resulted in isolation of individual components.
36. - ion, a hard base, does not normally coordinate or participate in hydrogen bonding. However, when no other donor is present to compete, the perchlorate ion exercises a donor capacity and can be monodentate, bridging bidentate, or chelating bidentate (Potier, J. Inorg. Chem. 1985, 24, 238). To our knowledge, the present finding represents the first example of a hydrogen-bonding self-assembly of perchlorate ions.
37. 2 modules. The rigid adamantane spacer in the bisamide ligand 1 appeared as a judicious choice to achieve this objective. Thus, the preference of Cu(II) ion for a four-coordinate square-planar geometry and the rigidity of the 1,3 adamantyl spacer forcing the ligand to act as a bis-bidentate rather than a tetradentate appear to be the most likely driving factors for the formation of an infinite assembly.
38. 2 modules. The rigid adamantane spacer in the bisamide ligand 1 appeared as a judicious choice to achieve this objective. Thus, the preference of Cu(II) ion for a four-coordinate square-planar geometry and the rigidity of the 1,3 adamantyl spacer forcing the ligand to act as a bis-bidentate rather than a tetradentate appear to be the most likely driving factors for the formation of an infinite assembly.
39. -1, sh = shoulder: 730 (60), 415 sh(75), 326 sh (920), 277 (11 600)] was also in agreement with the five-coordinated Cu(II) geometry (Hathaway, B. J. J. Chem. Soc., Dalton Trans. 1972, 1196. McLachlan, G. A.; Falton, G. D.; Martin, R. L.; Spiccia, L. Inorg. Chem. 1995, 34, 254).
40. -1, sh = shoulder: 730 (60), 415 sh(75), 326 sh (920), 277 (11 600)] was also in agreement with the five-coordinated Cu(II) geometry (Hathaway, B. J. J. Chem. Soc., Dalton Trans. 1972, 1196. McLachlan, G. A.; Falton, G. D.; Martin, R. L.; Spiccia, L. Inorg. Chem. 1995, 34, 254).
41. -1, sh = shoulder: 730 (60), 415 sh(75), 326 sh (920), 277 (11 600)] was also in agreement with the five-coordinated Cu(II) geometry (Hathaway, B. J. J. Chem. Soc., Dalton Trans. 1972, 1196. McLachlan, G. A.; Falton, G. D.; Martin, R. L.; Spiccia, L. Inorg. Chem. 1995, 34, 254).
42. The enzyme galactose oxidase provides a novel example of Cu(II) ion in a square-pyramidal coordination mode (Ito, N.; Phillips, S. E. V.; Stevens, C.; Ogel, Z. G.; McPherson, M. J.; Keen, J. N.; Yadav, K. D. S.; Knowles, P. F. Nature 1991, 350, 87).
43. The Cu-O and Cu-N distances in the Cu(II) complex of 1 correspond well to the reported values in the known square-pyramidal complexes of Cu(II) (Hathaway, B. J. Coord. Chem. Rev. 1982, 41, 423-487. Pajunen, A.; Nasakkala, M. Acta Crystallogr. 1980, B36, 1650. Pavelcik, F.; Majer, J. Acta Crystallogr. 1980, B36, 1645).
44. The Cu-O and Cu-N distances in the Cu(II) complex of 1 correspond well to the reported values in the known square-pyramidal complexes of Cu(II) (Hathaway, B. J. Coord. Chem. Rev. 1982, 41, 423-487. Pajunen, A.; Nasakkala, M. Acta Crystallogr. 1980, B36, 1650. Pavelcik, F.; Majer, J. Acta Crystallogr. 1980, B36, 1645).
45. The Cu-O and Cu-N distances in the Cu(II) complex of 1 correspond well to the reported values in the known square-pyramidal complexes of Cu(II) (Hathaway, B. J. Coord. Chem. Rev. 1982, 41, 423-487. Pajunen, A.; Nasakkala, M. Acta Crystallogr. 1980, B36, 1650. Pavelcik, F.; Majer, J. Acta Crystallogr. 1980, B36, 1645).
46. 2 to perchlorate ions.