Calix[4]pyrroles containing deep cavities and fixed walls. Synthesis, structural studies, and anion binding properties of the isomeric products derived from the condensation of p-hydroxyacetophenone and pyrrole [10]

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 11020-11021

  Anzenbacher Jr , Pavel ^a   Jursíková, Karolina ^a   Lynch, Vincent M ^a   Gale, Philip A ^b   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL STRUCTURE; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0344031616     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993195n     Document Type: Letter

References (26)

1. For representative examples of extended cavity calixarenes and resorcinarenes, see: (a) MacGillivray, L. R.; Atwood, J. L. Chem. Commun. 1999, 181-182. (b) Ma, S. H.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 4977-4981. Arduini, A.; Pochini, A.; Rizzi, A.; Sicuri, A. R.; Ugozzoli, F.; Ungaro, R. Tetrahedron 1992, 48, 905-912.
2. For representative examples of extended cavity calixarenes and resorcinarenes, see: (a) MacGillivray, L. R.; Atwood, J. L. Chem. Commun. 1999, 181-182. (b) Ma, S. H.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 4977-4981. Arduini, A.; Pochini, A.; Rizzi, A.; Sicuri, A. R.; Ugozzoli, F.; Ungaro, R. Tetrahedron 1992, 48, 905-912.
3. For representative examples of extended cavity calixarenes and resorcinarenes, see: (a) MacGillivray, L. R.; Atwood, J. L. Chem. Commun. 1999, 181-182. (b) Ma, S. H.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 4977-4981. Arduini, A.; Pochini, A.; Rizzi, A.; Sicuri, A. R.; Ugozzoli, F.; Ungaro, R. Tetrahedron 1992, 48, 905-912.
4. Baeyer A. Ber. Dtsch. Chem. Ges. 1886, 19, 2184-2185.
5. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141. Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1-8.
6. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141. Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1-8.
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10. Sessler, J. L.; Gale, P. A.; Genge, J. W. Chem. Eur. J. 1998, 4, 1095-1099.
11. Gale, P. A.; Sessler, J. L.; Allen, W. E.; Tvermoes, N. A.; Lynch, V. M. Chem. Commun. 1997, 665-666.
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13. (b) Gale, P. A.; Genge, J. W.; Král, V.; McKervey, M. A.; Sessler, J. L.; Walker, A. Tetrahedron Lett. 1997, 38, 8443-8444.
14. Turner, B.; Botoshansky, M.; Eichen, Y. Angew. Chem., Int. Ed. 1998, 37, 2475-2478.
15. The first examples of unsymmetrical, as opposed to the present deep-cavity, calixpyrroles were produced by the Russian chemists Chelintzev and Tronov. Among other accomplishments, they isolated a pure sample of a single configurational isomer of meso-tetramethyltetraethylcalix[4]pyrrole: (a) Chelintzev, V. V.; Tronov, B. V. J. Russ. Phys. Chem. Soc. 1916, 48, 105-155. (b) Chelintzev, V. V.; Tronov, B. V. J. Russ. Phys. Chem. Soc. 1916, 48, 1197-1209.
16. The first examples of unsymmetrical, as opposed to the present deep- cavity, calixpyrroles were produced by the Russian chemists Chelintzev and Tronov. Among other accomplishments, they isolated a pure sample of a single configurational isomer of meso-tetramethyltetraethylcalix[4]pyrrole: (a) Chelintzev, V. V.; Tronov, B. V. J. Russ. Phys. Chem. Soc. 1916, 48, 105-155. (b) Chelintzev, V. V.; Tronov, B. V. J. Russ. Phys. Chem. Soc. 1916, 48, 1197-1209.
17. Early studies of unsymmetrical meso-aryl-substituted calix[4]pyrroles were presented in the following: Sessler, J. L.; Anzenbacher, P., Jr.; Jursíková, K.; Miyaji, H.; Genge, J. W.; Tvermoes, N. A.; Allen, W. E.; Shriver, J. A.; Gale, P. A.; Král, V. Pure Appl. Chem. 1998, 70, 2401-2408.
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23. o)]), and a goodness of fit = 1.08 for 641 refined parameters.
24. In many cases, the NH proton resonance broadened considerably upon addition of anions. In these instances, the anion induced resonance shifts of the pyrrolic β-protons were used to calculate stability constants.
25. Wilcox, C. S. In Frontiers in Supramolecular Organic Chemistry and Photochemistry: Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, 1991.
26. -/2 ratios. For this same system, fluoride-hydroxyl interactions have also been observed in the solid state; cf. Supporting Information.