A Novel Ditopic Receptor and Reversal of Anion Binding Selectivity in the Presence and Absence of Bound Cation

Organic Letters

Volumn 5, Issue 26, 2003, Pages 4971-4974

  Tumcharern, Gamolwan ^a   Tuntulani, Thawatchai ^a   Coles, Simon J ^b   Hursthouse, Michael B ^b   Kilburn, Jeremy D ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ANION; BIPHENYL DERIVATIVE; CATION; DITOPIC RECEPTOR; PHOSPHATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RECEPTOR; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL BINDING; CHEMICAL REACTION; CRYSTAL STRUCTURE; REACTION ANALYSIS; RECEPTOR BINDING; SYNTHESIS;

ACETATES; CALIXARENES; CATIONS; PHENOLS; PHOSPHATES; SODIUM;

EID: 0346025410     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035894h     Document Type: Article

References (22)

1. Recent reviews that discuss ion-pair binding: Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 486. Gale P. A. Coord. Chem. Rev. 2003, 240, 191. See also Mahoney, J. M.; Beatty, A. M.; Smith B. D. J. Am. Chem. Soc. 2001, 123, 5847. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201 and citations therein.
2. Recent reviews that discuss ion-pair binding: Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 486. Gale P. A. Coord. Chem. Rev. 2003, 240, 191. See also Mahoney, J. M.; Beatty, A. M.; Smith B. D. J. Am. Chem. Soc. 2001, 123, 5847. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201 and citations therein.
3. Recent reviews that discuss ion-pair binding: Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 486. Gale P. A. Coord. Chem. Rev. 2003, 240, 191. See also Mahoney, J. M.; Beatty, A. M.; Smith B. D. J. Am. Chem. Soc. 2001, 123, 5847. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201 and citations therein.
4. Recent reviews that discuss ion-pair binding: Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 486. Gale P. A. Coord. Chem. Rev. 2003, 240, 191. See also Mahoney, J. M.; Beatty, A. M.; Smith B. D. J. Am. Chem. Soc. 2001, 123, 5847. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201 and citations therein.
5. Scheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 1996, 35, 1090. Webber, R. A.; Beer, P. D. J. Chem. Soc., Dalton Trans. 2003, 2249.
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12. -3, respectively. The asymmetric unit contains two molecules of water and one tertiary butyl group exhibits some disorder. Supplementary data have been deposited with the CCDC in CIF format with the deposition number CCDC224706.
13. 1H NMR spectrum), lack of solubilization was adjudged by the fact that the spectrum for the receptor after stirring with the sodium salt was unaltered relative to the spectrum of the receptor on its own.
14. Bisson, A. P.; Hunter, C. A.; Morales, J. C.; Young, K. Chem. Eur. J. 1998, 4, 845. Errors in the calculated association constants were estimated, based on quality of fit of the experimental data with the theoretical curve, and experimental errors in carrying out the experiment, as <10%. Association constants are therefore reported to 2 s.f. Detailed binding data and titration curves are provided in the Supplementary Information.
15. (a) Connors, K. A. Binding Constants, The Measurement of Molecular Complex Stability; Wiley: New York, 1987; p 24.
16. (b) Job, A. Ann. Chim. 1928, 9, 113.
17. CAUTION: perchlorate salts are potentially explosive.
18. Macomber, R. S. J. Chem. Educ. 1992, 69, 375. Errors in the calculated association constants were estimated, based on experimental errors in carrying out the experiment, as <10%. Association constants are therefore reported to 2 s.f.
19. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3099. See also: Camiolo, S.; Coles, S. J.; Gale, P. A.; Hursthouse, M. B.; Tizzard, G. J. Supramol. Chem. 2003, 15, 231.
20. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3099. See also: Camiolo, S.; Coles, S. J.; Gale, P. A.; Hursthouse, M. B.; Tizzard, G. J. Supramol. Chem. 2003, 15, 231.
21. Calixarene-derived receptors which change conformation on binding a metal cation and thereby allow anion binding have been described: Murakami, H.; Shinkai, S. Tetrahedron Lett. 1993, 34, 4237. Murakami, H.; Shinkai, S. Chem. Commun. 1993, 1533.
22. Calixarene-derived receptors which change conformation on binding a metal cation and thereby allow anion binding have been described: Murakami, H.; Shinkai, S. Tetrahedron Lett. 1993, 34, 4237. Murakami, H.; Shinkai, S. Chem. Commun. 1993, 1533.