Anion-dependent dimerization of a guanidiniocarbonyl pyrrole cation in DMSO

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1253-1256

  Schmuck, Carsten ^a   Heil, Martin ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFOXIDE; DRUG DERIVATIVE; GLYCINE; GUANIDINE; PYRROLE DERIVATIVE;

ALGORITHM; ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ALGORITHMS; BINDING SITES; DIMERIZATION; DIMETHYL SULFOXIDE; GLYCINE; GUANIDINE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 0035799889     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015596p     Document Type: Article

References (40)

1. (a) Schneider, H. J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley-VCH: Weinheim, 2000.
2. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: Chichester, 2000.
3. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
4. (d) Lehn, J.-M. Supramolecular Chemistry; Concepts and Perspectives; VCH: Weinheim, 1995.
5. (e) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
6. (a) Bishop, R. Synlett 1999, 1351-1359.
7. (b) Weber, E., Ed. Design of Organic Solids (Topics in Current Chemistry); Springer: Berlin Heidelberg, 1998; p 198.
8. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2328-2345.
9. (d) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989.
10. (e) Wright, J. D. Molecular Crystals; Cambridge University Press: Cambridge 1987.
11. (f) Chin, D. N.; Palmore, T. R.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2115-2132.
12. For review articles, see: (a) Schalley, C. A.; Rebek Jr., J. Chemical Encapsulation in Self-Assembling Capsules. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000.
13. (b) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286.
14. (c) Conn. M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
15. (a) For a general comment, see: Gellman, S. H. Chem. Rev. 1997, 97, 1231-1232. For examples of solvent effects on the strength of H bonds in complexes, see:
16. (b) Horvath, P.; Gergely, A.; Noszal, B. J. Chem. Soc., Perkin Trans. 1 1996, 1419-1422.
17. (c) Kelly, T. R.; Kim, M. H.; J. Am. Chem. Soc. 1994, 116, 7072-7080.
18. (d) Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-419.
19. For a recent example of a self-organizing system that functions in polar solvents, see: Grawe, T.; Schrader, T.; Gurrath, M.; Kraft, A.; Osterod, F. Org. Lett. 2000, 2, 29-32. See also references therein for earlier work.
20. (a) Schmuck, C. Eur. J. Org. Chem. 1999, 2397-2403.
21. (b) Schmuck, C. J. Org. Chem. 2000, 65, 2432-2437.
22. (c) Schmuck, C. Tetrahedron, in press.
23. Schmuck, C. Chem. Eur. J. 2000, 6, 709-718.
24. Dixon, R. D.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365-366.
25. Wilcox, C. S. In Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H. J., Dürr, H., Eds.; VCH: Weinheim, 1990.
26. (a) Connors, K. A. Binding Constants; Wiley: New York, 1987; Chapter 2 and 5.
27. (b) Davis, J. C., Jr.; Deb, K. K. Adv. Magn. Reson. 1970, 4, 201-270.
28. (a) Bangerter, B. W.; Chan, S. I. J. Am. Chem. Soc. 1969, 91, 3910-3921.
29. For a general discussion of chain-association equilibria studies by NMR, see: LaPlanche, L. A.; Thompson, H. B.; Rogers, M. T. J. Phys. Chem. 1965, 69, 1482-1488.
30. For other examples of endothermic binding in supramolecular systems, see: (a) Sebo, L.; Schweizer, B.; Diedrich, F. Helv. Chim. Acta 2000, 83, 80-92.
31. (b) Linton, B.; Hamilton, A. D. Tetrahedron 1999, 55, 6027-6038.
32. (c) Berger, M.: Schmidtchen, F. P. J. Am. Chem. Soc. 1999, 121, 9986-9993.
33. (d) Berger, M.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 2694-2696.
34. (e) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85.
35. (a) Davis, A. M.; Teague, S. J. Angew. Chem., Int. Ed. 1999, 38, 736-749.
36. (b) Williams, D. H.; Westwell, M. S. Chem. Soc. Rev. 1998, 27, 57-64.
37. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufiled, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
38. For recent work on the importance of π-stacking in supramolecular aggregates, see, for example: (a) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
39. (b) Sirish, M.; Schneider, H. J. J. Am. Chem. Soc. 2000, 122, 5881-5882.
40. (c) Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222.