Abstract
Hydrogen bonding is used to control supramolecular structure in two distinct ways. The first involves intramolecular hydrogen bonds to stabilize linear and helical conformations in synthetic oligomers. The second uses intermolecular hydrogen bonding to direct the self-assembly of several interacting subunits.
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References
Lindsey, J. S. New J. Chem. 1991, 15, 153. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science (Washington, D.C.) 1992, 254, 1312.
A family of novel polypeptide-like structures based on vinylogous amino acids has recently been reported; Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 774, 6568.
Intramolecular hydrogen bonds have recently been used to control the structure of oligourea scaffolds; Nowick, J. S.; Powell, N. A.; Martinez, E. J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763, and bis-acylguanidinium receptors; Dixon, R. P.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 365.
A related approach has been used to prepare cyclic anthranilamide oligomers, a) Hoorfar, A.; Ollis, W. D.; Stoddart, J. F. Tetrahedron Lett.. 1980, 4211. b) Feigel, M.; Lugert, G. Liebigs Ann. Chem.. 1989, 1089.
Similar intramolecular hydrogen bonds have been seen in a family of anthranilic acid-amino acid adducts; Feigel, M.; Lugert, G.; Manero, J.; Bremer, M. Z. Naturforsch. 1989, 44b, 1109. Feigel, M.; Lugert, G.; Manero, J.; Bremer, M. Z. Naturforsch. 1990, 45b, 258.
Rychlewska, U.; Gdaniec, M. Acta Cryst. 1977, B33, 3555. Brzezinski, B.; Zundel, G.; Krämer, R. Chem Phys. Lett. 1986, 124, 395.
Several helical structures stabilized by metal template effects have been reported; Constable, E. C. Angew. Chem. Int. Ed. 1991, 30, 1450. Williams, A. F.; Piguet, C.; Bernardinelli, G. Angew. Chem. Int. Ed. 1991, 30, 1490. Koert, U.; Harding, M. M.; Lehn, J. M. Nature, 1990, 346, 339. Dietrich-Bucheker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J. P. Angew. Chem. Int. Ed. 1990, 29, 1202. Constable, E. C.; Ward, M. D.; Tocher, D. A. J. Chem. Soc. Dalton Trans. 1991, 1675.
For examples of helical molecules stabilized by covalent interactions see; Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787 and references therein. Fritsch, R.; Hartmann, E.; Andert, D.; Mannschreck, A. Chem. Ber. 1992, 125, 849. Gange, D.; Magnus, P.; Bass, L.; Arnold, E. V.; Clardy, J. J. Am. Chem.Soc. 1980, 102, 2134.
Repeated attempts to confirm helix formation in solution by adding chiral shift reagents were unsuccessful, even at low temperature, presumably due to the fast exchange between right and left handed helical forms.
The five-membered ring intramolecular hydrogen bonds of the simple pyridine-2,6-dicarboxamide are expected to be weak due to the reduced basicity of the pyridine.11 However, the conformation shown in 9 is still expected to be favored as the alternative (near-planar) conformations, involving ≈ 180° rotation about one or both pyridine-CO bonds, should be destablized by electrostatic repulsion between the pyridine-N and carbonyl-O.
Newkome, G. R.; Fronczek, F.; Kohli, D. K. Acta Cryst. 1981, B37, 2114. Weber, E.; Newkome, G. R.; Fronczek, F.; Franken, S. J. Inclusion Phenom. 1988, 6, 1.
Kessler, H. Angew. Chem. Int. Ed. 1982, 21, 512.
Garcia-Tellado, F.; Goswami, S.; Chang, S. K.; Geib, S.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393
Garcia-Tellado, F.; Geib, S. J.; Goswami, S.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 9265.
Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 6409. Seto, C. T.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 712. Zimmerman, S. C.; Duerr, B. F. J. Org. Chem. 1992, 57, 2215.
Seto, C. T.; Mathias, J. P.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1321.
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Hamilton, A.D., Hamuro, Y., Yang, J., Geib, S.J., Fan, E. (1994). Intra- and Intermolecular Hydrogen Bonding Control of Supramolecular Structure. In: Wipff, G. (eds) Computational Approaches in Supramolecular Chemistry. NATO ASI Series, vol 426. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-1058-7_6
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DOI: https://doi.org/10.1007/978-94-011-1058-7_6
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