Complexation-induced unfolding of heterocyclic ureas: A hydrogen-bonded, sheetlike heterodimer [5]

Journal of the American Chemical Society

Volumn 122, Issue 15, 2000, Pages 3779-3780

  Corbin, Perry S ^a   Zimmerman, Steven C ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; HYDROGEN; UREA DERIVATIVE;

COMPLEX FORMATION; HYDROGEN BOND; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0034685514     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992830m     Document Type: Letter

References (25)

1. See, e.g.: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296. (c) Kelly, J. W., Ed., Bioorg. Med. Chem. 1999, 7, issue 1 (Symposium-in-Print). (d) Gong, B.; Yan, Y.; Zeng, H.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607-5608.
2. See, e.g.: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296. (c) Kelly, J. W., Ed., Bioorg. Med. Chem. 1999, 7, issue 1 (Symposium-in-Print). (d) Gong, B.; Yan, Y.; Zeng, H.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607-5608.
3. See, e.g.: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296. (c) Kelly, J. W., Ed., Bioorg. Med. Chem. 1999, 7, issue 1 (Symposium-in-Print). (d) Gong, B.; Yan, Y.; Zeng, H.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607-5608.
4. See, e.g.: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296. (c) Kelly, J. W., Ed., Bioorg. Med. Chem. 1999, 7, issue 1 (Symposium-in-Print). (d) Gong, B.; Yan, Y.; Zeng, H.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607-5608.
5. See, e.g.: (a) Hamuro, Y.; Geib, S. J.; Hamilton A. D. J. Am. Chem. Soc. 1997, 119, 10587-10593. (b) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796. (c) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68. (d) Ohkita, M.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 3471-3481.
6. See, e.g.: (a) Hamuro, Y.; Geib, S. J.; Hamilton A. D. J. Am. Chem. Soc. 1997, 119, 10587-10593. (b) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796. (c) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68. (d) Ohkita, M.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 3471-3481.
7. See, e.g.: (a) Hamuro, Y.; Geib, S. J.; Hamilton A. D. J. Am. Chem. Soc. 1997, 119, 10587-10593. (b) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796. (c) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68. (d) Ohkita, M.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 3471-3481.
8. See, e.g.: (a) Hamuro, Y.; Geib, S. J.; Hamilton A. D. J. Am. Chem. Soc. 1997, 119, 10587-10593. (b) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796. (c) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68. (d) Ohkita, M.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 3471-3481.
9. To our knowledge, only peptides have been reported to be capable of controlled changes between two discrete secondary structures: (a) Schenck, H. L.; Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 12487-12494. (b) Mutter, M.; Gassmann, R.; Buttkus, U.; Altmann, K.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1514-1516.
10. To our knowledge, only peptides have been reported to be capable of controlled changes between two discrete secondary structures: (a) Schenck, H. L.; Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 12487- 12494. (b) Mutter, M.; Gassmann, R.; Buttkus, U.; Altmann, K.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1514-1516.
11. For a thermally irreversible change in a folded oligomer see: Nguyen, J. Q.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639-2640.
12. For robust, multiply H-bonded complexes see, e.g.: (a) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710-9711. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729. (c) Lüning, U.; Kuhl, C. Tetrahedron Lett. 1998, 39, 5735-5738. (d) 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. (e) Zimmerman, S. C.; Murray, T. J. In Computational Approaches in Supramolecular Chemistry; NATO ASI Series, Vol. 426; Wipff, G., Ed.; Kluwer: Amsterdam, 1994; pp 109-115.
13. For robust, multiply H-bonded complexes see, e.g.: (a) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710-9711. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729. (c) Lüning, U.; Kuhl, C. Tetrahedron Lett. 1998, 39, 5735-5738. (d) 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. (e) Zimmerman, S. C.; Murray, T. J. In Computational Approaches in Supramolecular Chemistry; NATO ASI Series, Vol. 426; Wipff, G., Ed.; Kluwer: Amsterdam, 1994; pp 109-115.
14. For robust, multiply H-bonded complexes see, e.g.: (a) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710-9711. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729. (c) Lüning, U.; Kuhl, C. Tetrahedron Lett. 1998, 39, 5735-5738. (d) 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. (e) Zimmerman, S. C.; Murray, T. J. In Computational Approaches in Supramolecular Chemistry; NATO ASI Series, Vol. 426; Wipff, G., Ed.; Kluwer: Amsterdam, 1994; pp 109-115.
15. For robust, multiply H-bonded complexes see, e.g.: (a) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710-9711. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729. (c) Lüning, U.; Kuhl, C. Tetrahedron Lett. 1998, 39, 5735-5738. (d) 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. (e) Zimmerman, S. C.; Murray, T. J. In Computational Approaches in Supramolecular Chemistry; NATO ASI Series, Vol. 426; Wipff, G., Ed.; Kluwer: Amsterdam, 1994; pp 109-115.
16. For robust, multiply H-bonded complexes see, e.g.: (a) Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710-9711. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729. (c) Lüning, U.; Kuhl, C. Tetrahedron Lett. 1998, 39, 5735-5738. (d) 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. (e) Zimmerman, S. C.; Murray, T. J. In Computational Approaches in Supramolecular Chemistry; NATO ASI Series, Vol. 426; Wipff, G., Ed.; Kluwer: Amsterdam, 1994; pp 109-115.
17. All compounds described herein gave correct elemental analyses and had spectral properties consistent with the assigned structures.
18. Bernstein, J.; Stearns, B.; Shaw, E.; Lott, W. A. J. Am. Chem. Soc. 1947, 69, 1151-1158.
19. For the application of graph notation to H-bonding motifs see: Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
20. For IR and NMR studies of: (a) N-methyl-N′-2-pyridyl urea: Sudha, L. V.; Sathyanarayana, D. N. J. Mol. Struct. 1984, 125, 89-96. (b) N,N′-di- 2-pyridyl thiourea: Sudha, L. V.; Sathyanarayana, D. N.; Bharati, S. N. Magn. Reson. Chem. 1987, 25, 474-479. (c) N,N′-di-2-(6-methylpyridyl) urea: Vdovichemnko, A.; Chervinskii, A. Y.; Galat, V. F.; Kaplan, L. Sov. Prog. Chem. 1990, 46, 108-110.
21. For IR and NMR studies of: (a) N-methyl-N′-2-pyridyl urea: Sudha, L. V.; Sathyanarayana, D. N. J. Mol. Struct. 1984, 125, 89-96. (b) N,N′-di-2-pyridyl thiourea: Sudha, L. V.; Sathyanarayana, D. N.; Bharati, S. N. Magn. Reson. Chem. 1987, 25, 474-479. (c) N,N′-di-2-(6-methylpyridyl) urea: Vdovichemnko, A.; Chervinskii, A. Y.; Galat, V. F.; Kaplan, L. Sov. Prog. Chem. 1990, 46, 108-110.
22. For IR and NMR studies of: (a) N-methyl-N′-2-pyridyl urea: Sudha, L. V.; Sathyanarayana, D. N. J. Mol. Struct. 1984, 125, 89-96. (b) N,N′-di- 2-pyridyl thiourea: Sudha, L. V.; Sathyanarayana, D. N.; Bharati, S. N. Magn. Reson. Chem. 1987, 25, 474-479. (c) N,N′-di-2-(6-methylpyridyl) urea: Vdovichemnko, A.; Chervinskii, A. Y.; Galat, V. F.; Kaplan, L. Sov. Prog. Chem. 1990, 46, 108-110.
23. For example, N,N′-(2-methylphenyl)urea, δ (NH) ≈ 6.4 ppm; N-butyl-N′-2-(1,8-naphthyridinyl)urea, δ (NH) ≈ 7.2 ppm.
24. Wilcox, C. S. Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H. J., Durr, H., Eds.; VCH: New York, 1991, 123-143.
25. Dilution studies indicated that N,N′-di-2-pyridyl urea dimerized weakly in chloroform and in the same manner as observed in the solid-state.