The pinched cone conformation of calix[4]arenes: Noncovalent rigidification of the calix[4]arene skeleton

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3476-3481

  Scheerder, Jurgen ^a   Vreekamp, Remko H ^a   Engbersen, Johan F J ^a   Verboom, Willem ^a   Van Duynhoven, John P M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001698343     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600262     Document Type: Article

References (46)

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15. For recent examples of covalent rigidification of the calix[4]-arene skeleton, see: (a) Arduini, A.; Fanni, S.; Manfredi, G.; Pochini, A.; Ungaro, R.; Sicuri, A. R.; Ugozzoli, F. J. Org. Chem. 1995, 60, 1448. (b) Arduini, A.; Fanni, S.; Pochini, A.; Sicuri, A. R.; Ungaro, R. Tetrahedron 1995, 51, 7951.
16. For recent examples of covalent rigidification of the calix[4]-arene skeleton, see: (a) Arduini, A.; Fanni, S.; Manfredi, G.; Pochini, A.; Ungaro, R.; Sicuri, A. R.; Ugozzoli, F. J. Org. Chem. 1995, 60, 1448. (b) Arduini, A.; Fanni, S.; Pochini, A.; Sicuri, A. R.; Ungaro, R. Tetrahedron 1995, 51, 7951.
17. For stabilization of the pinched cone conformation via upper rim bridging, see: (c) Goldmann, H.; Vögt, W.; Paulus, E.; Böhmer, V. J. Am. Chem. Soc. 1988, 110, 6811. (d) Böhmer, V.; Vogt, W.; Goldmann, H.; McKervey, A. M.; Owens, M.; Cremin, S.; Collins, E. M. J. Org. Chem. 1990, 55, 2569.
18. For stabilization of the pinched cone conformation via upper rim bridging, see: (c) Goldmann, H.; Vögt, W.; Paulus, E.; Böhmer, V. J. Am. Chem. Soc. 1988, 110, 6811. (d) Böhmer, V.; Vogt, W.; Goldmann, H.; McKervey, A. M.; Owens, M.; Cremin, S.; Collins, E. M. J. Org. Chem. 1990, 55, 2569.
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25. (b) Exchange connectivities in the NOESY spectrum were identified by ROESY experiments where ROE and exchange connectivities have opposite signs. For an introduction to ROESY spectroscopy, see: Bothner-By, A. A.; Stephens, R. L.; Lee, L.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811.
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27. 3 solution, are equal, 2.7 Å. Scheerder, J. Ph. D. Thesis, University of Twente, 1995.
28. 15
29. c < 1) are observed for small molecules, nonviscous solutions, high temperature, and weak magnetic fields. See ref 15.
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35. 6 concerning the shifts of the aromatic hydrogens.
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39. The two aromatic rings are almost parallel and their closest distance is 4.51 Å, indicating that π-π stacking is unlikely to contribute to the stability of the pinched cone conformation. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
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45. Quanta was purchased from Molecular Simulations, Inc., Burlington, MA.
46. 12