The acidity of calix[5]arenes and their linear analogues

Tetrahedron

Volumn 55, Issue 25, 1999, Pages 7819-7828

  Schmidt, Christian ^a   Kumar, Manoj ^a   Vogt, Walter ^a   Böhmer, Volker ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Acidity; Calixarenes; Macrocycles

Indexed keywords

CALIXARENE;

ACIDITY; ARTICLE; CONFORMATIONAL TRANSITION; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

ARENE;

EID: 0033580805     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00396-8     Document Type: Article

References (26)

1. For a review covering also the historical development see: C. D. Gutsche, Calixarenes, ed. F. Stoddart, Royal Society of Chemistry, Cambridge 1989
2. For further reviews on calixarenes see: a) V. Böhmer, Angew. Chem. 1995, 107, 785-818,
3. Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745;
4. b) C. D. Gutsche, Calixarenes Revisited, ed. F. Stoddart, Royal Society of Chemistry, Cambridge 1998
5. For early reports compare: a) V. Böhmer, E. Schade, W. Vogt, Makromol. Chem., Rapid Commun. 1984, 5, 221-224;
6. b) S. Shinkai, K. Araki, H. Koreishi, T. Tsubaki, O. Manabe, 1986, 1351-1354
7. For a general review of thermodynamic data of calixarenes see: A. F. Danil de Namor, R. M. Cleverley, M. L. Zapata-Omachea, Chem. Rev. 1998, 98, 2495-2525
8. S. Shinkai, K. Araki, P. D. J. Grootenhuis, D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1991, 1883-1886
9. I. Yoshida, N. Yamato, F. Sagara, D. Ishii, K. Ueno, S. Shinkai, Bull. Chem. Soc. Jpn. 1992, 65, 1012-1015
10. G. Arena, R. Cali, G. G. Lombardo, E. Rizzarelli, D. Sciotto, R. Ungaro, A. Casnati, Supramol. Chem. 1992, 1, 19-24
11. Of course these informations are restricted mainly to the first dissociation step, although with dinitro-calix[4]arenes the second step could be characterised also.
12. M. Backes, V. Böhmer, G. Ferguson, C. Grüttner, C. Schmidt, W. Vogt, K. Ziat, J. Chem. Soc., Perkin Trans. 2, 1997, 1193-1200
13. S. W. Keller, G. M. Schuster, F. L. Tobiason, Polym. Mater. Sci. Eng. 1987, 57, 906-910
14. 1H NMR data see ref. 2a
15. See for instance: J. F. Gallagher, G. Ferguson, V. Böhmer, D. Kraft, Acta Cryst. 1994, C50, 73-77
16. S. E. Biali, V. Böhmer, I. Columbus, G. Ferguson, C. Grüttner, F. Grynszpan, E. F. Paulus, I. Thondorf, J. Chem. Soc., Perkin Trans. 2, 1998, 2261-2269
17. K. No, K. M. Kwan, Synthesis, 1996, 1293-1295
18. D. Stewart, C. D. Gutsche, Org. Prep. Proc. Int. 1993, 25, 137-139
19. A larger cyclic oligomer e.g. a calix[10]arene would show the same ratio, but as a more flexible molecule, no pairs of doublets for the methylene protons.
20. a = 8.73).
21. J. W. Steed, C. P. Johnson, C. L. Barnes, R. K. Juneja, J. L. Atwood, S. Reilly, R. L. Hollis, P. H. Smith, D. L. Clark, J. Am. Chem. Soc. 1995, 117, 11426-11433
22. G. Arena, A. Contino, G. G. Lombardo, D. Sciotto, Thermochim. Acta 1995, 264, 1-11
23. J.-P. Scharff, M. Mahjoubi, R. Perrin, New J. Chem. 1991, 15, 883-887
24. a (0.68 versus 0.46 for 3a/3b and 5a/5b) by the different flexibility of the linear and the cyclic oligomers making the assistance by the p-chlorophenol units more or less effective, however, the results should not be overinterpreted.
25. V. Böhmer, E. Schade, C. Antes, J. Pachta, W. Vogt, H. Kämmerer, Makromol. Chem. 1983, 184, 2361-2376
26. a1, which not even requires a pure compound, as long as impurities eventually present do not change their absorbance in the relevant pH range.