Comparison of an HXH three-center hydrogen bond with alternative two-center hydrogen bonds in a model system

Organic Letters

Volumn 1, Issue 1, 1999, Pages 11-13

  Yang, Jihong ^a   Christianson, Laurie A ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002973705     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9900010     Document Type: Article

References (46)

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23. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
24. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
25. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
26. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
27. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
28. 3), which suggested that this hydrogen-bonded conformation would not be significantly populated. This prediction is likely to be reliable, since calculations of this type often over-estimate the tendency for intramolecular hydrogen bond formation (Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377). Monte Carlo-stochastic dynamics method: Still, W. C.; Guarnieri, F.J. Comput. Chem. 1994, 15, 1302. AMBER force field: Weiner, S.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230. AMBER* modification: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747. MacroModel: Mohamdi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. GB/SA solvation: Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
29. (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991 ,113, 1164.
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31. (c) For related work, see: Gung, B. W.; Zhu, Z.; Zou, D.; Everingham, B.; Oyeamalu, A.; Crist, R. M.; Baudlier, R. J. Org. Chem. 1998, 63, 5750, and references therein.
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35. (a) Cung, M. T.; Marraud, M.; Néel, J. In Proceedings of the 5th Jerusalem Symposium on Quantum Chemisty and Biochemistry; Bergman, E., Pullman, B., Eds.; Israel Academy of Sciences and Humanities: Jerusalem, 1973; pp 69ff. (b) Reference 6b.
36. 14N-H stretch.
37. Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774.
38. The extent to which a hydrogen-bonded N-H stretch band is shifted from its non-hydrogen-bonded position should be directly related to the strength of the hydrogen bond: Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, 1960. However, positions observed for amide N-H stretch bands may be influenced by Fermi resonance: Miyazawa, T. J. Mol. Spectroscopy 1960, 4, 168.
39. The extent to which a hydrogen-bonded N-H stretch band is shifted from its non-hydrogen-bonded position should be directly related to the strength of the hydrogen bond: Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, 1960. However, positions observed for amide N-H stretch bands may be influenced by Fermi resonance: Miyazawa, T. J. Mol. Spectroscopy 1960, 4, 168.
40. The IR-derived thermodynamic parameters derived for 1 are reproducible to within 10% in parallel independent determinations. Systematic error in these values, however, is difficult to evaluate. We have previously shown that IR-derived and NMR-derived enthalpy values agree well in related systems, but that agreement can be poorer for entropy values (refs 6a and 6b).
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