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Volumn 119, Issue 42, 1997, Pages 9956-9964

Binding features of molecular clips. Separation of the effects of hydrogen bonding and π-π interactions

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; HETEROCYCLIC COMPOUND;

EID: 0030723408     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970805f     Document Type: Article
Times cited : (133)

References (69)
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    • Recent reviews: (a) Cram, D. J. Top. Curr. Chem. 1981, 98, 43. (b) Schneider, H.-J. Angew. Chem. 1991, 103, 1419. (c) Diederich, F. Angew. Chem. 1988, 100, 372. (d) Seel, C.; Vögtle, F. Angew. Chem. 1992, 104. 542. (d) Izatt. Chem. Rev. 1995, 95 and references cited therein. (e) Izatt, R. M.; Bradshaw, J. S.; Pawlak, K.; Bruening, R. L.; Tarbet, B. J. Chem. Rev. 1992, 92, 1261 and references cited therein. (f) Various authors in Tetrahedron 1995, 57, Vol. 2, topic molecular recognition. (g) Cram, D. J. Nature 1992, 356, 29. (h) Zimmerman, S. C. Bioorganic Chemistry Frontiers 2: Springer-Verlag: Berlin, Heidelberg, 1991; p 33. (i) Hamilton, A. D. Bioorganic Chemistry Frontiers 2; Springer-Verlag: Berlin, Heidelberg, 1991; p 115. (j) Cram, D. J. Angew. Chem. 1988, 100, 1041. (k) Lehn, J.-M. Angew. Chem. 1988, 100, 92.
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    • For recent studies of weak noncovalent interactions, in particular edge-to-face π-π interactions by a double mutant cycle, see: (a) Adams, H.; Carver, F. J.; Hunter, C. H.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542 and references therein. (b) Schneider, H.- J.; Angew. Chem., Int. Ed. Engl. 1997, 36, 1072. (c) Searle, M. C.; Westwell, M. S.; Williams, D. H.; J. Chem. Soc., Perkin Trans. 2 1995, 141.
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    • For recent studies of weak noncovalent interactions, in particular edge-to-face π-π interactions by a double mutant cycle, see: (a) Adams, H.; Carver, F. J.; Hunter, C. H.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542 and references therein. (b) Schneider, H.- J.; Angew. Chem., Int. Ed. Engl. 1997, 36, 1072. (c) Searle, M. C.; Westwell, M. S.; Williams, D. H.; J. Chem. Soc., Perkin Trans. 2 1995, 141.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1072
    • Schneider, H.J.1
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    • For recent studies of weak noncovalent interactions, in particular edge-to-face π-π interactions by a double mutant cycle, see: (a) Adams, H.; Carver, F. J.; Hunter, C. H.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542 and references therein. (b) Schneider, H.- J.; Angew. Chem., Int. Ed. Engl. 1997, 36, 1072. (c) Searle, M. C.; Westwell, M. S.; Williams, D. H.; J. Chem. Soc., Perkin Trans. 2 1995, 141.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 141
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    • note
    • 30
  • 48
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    • note
    • The average structure determined by Molecular Dynamics calculation using the CHARMm Force Field gave approximately the same complex geometry as a minimalization (ABNR; CHARMm Force Field), i.e., the guest molecule shifted towards the oxygen carbonyl atom.
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    • Thesis, Utrecht
    • Niele F. Thesis, Utrecht, 1987;.
    • (1987)
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  • 55
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    • To be published
    • 2 group. This is additional proof for the fact that the thiocarbonyl groups are not involved in hydrogen bonding. Gieling, G.; Scheeren, H.; Nolte, R. J. M. To be published.
    • Gieling, G.1    Scheeren, H.2    Nolte, R.J.M.3
  • 58
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    • note
    • It should be noted that the same features which are responsible for a difference in association constants may also alter the aromatic ring current. Hence the calculations are only approximate.
  • 59
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    • Stymme et al. have found a much stronger substituent dependency of the OH stretching frequency for substituted phenols which were complexed to dimethylacetamide. The OH bond in these complexes, however, was directed to the n-electrons and not toward the π electrons which is the case in our complexes. Stymne, B.; Stymne, H.; Wettermark, G. J. Am. Chem. Soc. 1973, 95, 3490.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3490
    • Stymne, B.1    Stymne, H.2    Wettermark, G.3


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