Secondary effects in flexible hydrogen bonding networks

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 9881-9890

  Gardner, Robb R ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG STRUCTURE; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; QUANTUM CHEMISTRY; THEORY;

EID: 0030748320     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00333-5     Document Type: Article

References (36)

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19. For previous studies from our laboratory involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. (b) Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 4228. (e) Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774. (f) Ref. 8a.
20. For previous studies from our laboratory involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. (b) Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 4228. (e) Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774. (f) Ref. 8a.
21. For previous studies from our laboratory involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. (b) Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 4228. (e) Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774. (f) Ref. 8a.
22. For previous studies from our laboratory involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. (b) Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 4228. (e) Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774. (f) Ref. 8a.
23. For previous studies from our laboratory involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164. (b) Liang, G.-B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440. Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 4228. (e) Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774. (f) Ref. 8a.
24. For other studies involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89, and references therein. (b) Tsang, K. Y.; Kiaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988, and references therein. (c) Winningham, M. J.; Sogah, D. Y. J. Am. Chem. Soc. 1994, 116, 11173. Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482. (e) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
25. For other studies involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89, and references therein. (b) Tsang, K. Y.; Kiaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988, and references therein. (c) Winningham, M. J.; Sogah, D. Y. J. Am. Chem. Soc. 1994, 116, 11173. Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482. (e) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
26. For other studies involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89, and references therein. (b) Tsang, K. Y.; Kiaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988, and references therein. Winningham, M. J.; Sogah, D. Y. J. Am. Chem. Soc. 1994, 116, 11173. Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482. (e) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
27. For other studies involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89, and references therein. (b) Tsang, K. Y.; Kiaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988, and references therein. (c) Winningham, M. J.; Sogah, D. Y. J. Am. Chem. Soc. 1994, 116, 11173. Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482. (e) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
28. For other studies involving qualitative and quantitative interpretation of N-H stretch region IR data, see: (a) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89, and references therein. (b) Tsang, K. Y.; Kiaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988, and references therein. (c) Winningham, M. J.; Sogah, D. Y. J. Am. Chem. Soc. 1994, 116, 11173. Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482. (e) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
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30. (b) Burgess, A. W.; Scheraga, H. A. Biopolymers 1973, 12, 2177.
31. Dado, G. P., Ph.D. Thesis, University of Wisconsin - Madison, 1993.
32. A is the mass of atom A and MB is the mass of atom B. (Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th Ed.; John Wiley & Sons: New York, 1991, p. 93).
33. For interpretation of ΔδNH/ΔT data obtained in nonpolar solvents, see: (a) Ref. 12a. (b) Stevens, E. S.; Sugawara, N.; Bonara, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048.
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35. (b) Tereshko, V.; Navarro, E.; Puiggali, J.; Subirana, J. A. Macromolecules 1993, 26, 7024.
36. Ninomiya, K.; Shiori, T.; Yamada, S. Tetrahedron 1974, 30, 2151.