Anion recognition by diureido-calix[4]arenes in the 1,3-alternate conformation

New Journal of Chemistry

Volumn 33, Issue 3, 2009, Pages 612-619

  Cuřínová, Petra ^a,b   Stibor, Ivan ^a   Budka, Jan ^a   Sýkora, Jan ^b   Lang, Kamil ^c   Lhoták, Pavel ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

^c INSTITUTE OF MATHEMATICS   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBOXYLIC ACID DERIVATIVE; DIUREIDO CALIXARENE; RECEPTOR; SOLVENT; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COMPARATIVE STUDY; COMPLEX FORMATION; CONFORMATION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 61849099478     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b816790g     Document Type: Article

References (57)

1. J. L. Sessler, P. A. Gale and W.-S. Cho, Anion Receptor Chemistry, The Royal Society of Chemistry, Cambridge, 2006
2. Anion Sensing, in Topics in Current Chemistry, ed., I. Stibor, Springer, Berlin, 2005, vol. 255
3. P. A. Gale Coord. Chem. Rev. 2001 213 79
4. P. A. Gale Coord. Chem. Rev. 2000 199 181
5. P. D. Beer E. J. Hayes Coord. Chem. Rev. 2003 240 167
6. M. D. Best S. L. Tobey E. V. Anslyn Coord. Chem. Rev. 2003 240 3
7. C. Suksai T. Tuntulani Chem. Soc. Rev. 2003 192
8. R. J. Fitzmaurice G. M. Kyne D. Dougheret J. D. Kilburn J. Chem. Soc., Perkin Trans. 1 2002 841
9. P. A. Gale P. D. Beer Angew. Chem., Int. Ed. 2001 40 487
10. Supramolecular Chemistry of Anions, eds., A. Bianchi, K. Bowman-James, and, E. Garcia-Espana, Wiley-VCH, New York, 1997
11. F. P. Schmidtchen M. Berger Chem. Rev. 1997 97 1609
12. B. J. Hay T. K. Firman B. A. Moyer J. Am. Chem. Soc. 2005 127 1810
13. C. R. Bondy S. J. Loeb Coord. Chem. Rev. 2003 240 77
14. K. Choi A. D. Hamilton Coord. Chem. Rev. 2003 240 101
15. P. D. Beer A. G. Cheetham M. G. B. Drew O. D. Fox E. J. Hayes T. D. Rolls Dalton Trans. 2003 603
16. Calixarenes 2001, eds., Z. Asfari, V. Böhmer, J. Harrowfield, and, J. Vicens, Kluwer Academic Publishers, Dordrecht, 2001
17. L. Mandolini and R. Ungaro, Calixarenes in Action, Imperial College Press, London, 2000
18. C. D. Gutsche, Calixarenes Revisited, Monographs in Supramolecular Chemistry, ed., J. F. Stoddart, The Royal Society of Chemistry, Cambridge, 1998, vol. 6
19. Calixarenes 50th Anniversary: Commemorative Issue, eds., J. Vicens, Z. Asfari, and, J. M. Harrowfield, Kluwer Academic Publishers, Dordrecht, 1994
20. Calixarenes: A Versatile Class of Macrocyclic Compounds, eds., J. Vicens, and, V. Böhmer, Kluwer Academic Publishers, Dordrecht, 1991
21. A. Casnati, F. Sansone and R. Ungaro, Calixarene Receptors in Ion Recognition and Sensing, in Advances in Supramolecular Chemistry, ed., G. W. Gokel, Cerberus Press Inc., South Miami, FL, 2004, vol. 9, p. 169
22. P. Lhoták, Anion Receptors Based on Calixarenes, in Anion Sensing in Topics in Current Chemistry, ed., I. Stibor, Springer, Berlin, 2005, vol. 255, p. 65, and references cited therein
23. A. V. Yakovenko V. I. Boyko V. I. Kalchenko L. Baldini A. Casnati F. Sansone R. Ungaro J. Org. Chem. 2007 72 3223
24. B. Schazmann D. Diamond New J. Chem. 2007 31 587
25. P. A. Gale Coord. Chem. Rev. 2003 240 191
26. M. M. G. Antonisse D. N. Reinhoudt Chem. Commun. 1998 443
27. I. Stibor S. M. H. Dana P. Lhoták J. Hodačová J. Koča M. čajan Gazz. Chim. Ital. 1997 127 673
28. M. čajan I. Stibor J. Koča J. Phys. Chem. A 1999 103 3778
29. M. čajan J. Damborský I. Stibor J. Koča J. Chem. Inf. Comput. Sci. 2000 40 1151
30. I. Stibor R. Holakovský A. M. Mustafina P. Lhoták Collect. Czech. Chem. Commun. 2004 69 365
31. J. Budka P. Lhoták V. Michlová I. Stibor Tetrahedron Lett. 2001 42 1583
32. V. šťastný P. Lhoták V. Michlová I. Stibor J. Sykora Tetrahedron 2002 58 7207
33. M. Dudič P. Lhoták I. Stibor K. Lang P. Prošková Org. Lett. 2003 5 149
34. P. Lhoták J. Svoboda, Jr I. Stibor Tetrahedron 2006 62 1253
35. A. Krajewska P. Lhoták H. Radecka Sensors 2007 7 1655
36. I. Stibor J. Budka V. Michlová M. Tkadlecová M. Pojarová P. Cuřínová P. Lhoták New J. Chem. 2008 32 1597
37. J. D. Van Loon A. Arduini L. Coppi W. Verboom A. Pochini R. Ungaro S. Harkema D. N. Reinhoudt W. Verboom J. Org. Chem. 1990 55 5639
38. A. Arduini M. Fabbi M. Mantovani L. Mirone A. Pochini J. Org. Chem. 1995 60 1454
39. S. Datta Z. Asfari S. Harkema D. N. Reinhoudt J. Org. Chem. 1992 57 5394
40. A. Casnati F. Bonetti F. Sansone F. Ugozzoli R. Ungaro Collect. Czech. Chem. Commun. 2004 69 1063
41. S. K. Sharma C. D. Gutsche J. Org. Chem. 1996 61 2564
42. O. Struck L. A. J. Chrisstoffels R. J. W. Lugtenberg W. Verboom G. J. van Hummel S. Harkema D. N. Reinhoudt J. Org. Chem. 1997 62 2487
43. Z. Liang Z. Liu L. Jiang Y. Gao Tetrahedron Lett. 2007 48 1629
44. G. Mislin E. Graf M. W. Hosseini Tetrahedron Lett. 1996 37 4503
45. A. M. A. van Wageningen E. Snip W. Verboom D. N. Reinhoudt H. Boerrigter Liebigs Ann. 1997 2235
46. R. K. Castellano J. Rebek Jr J. Am. Chem. Soc. 1998 120 3657
47. A. Soi W. Bauer H. Mauser C. Moll F. Hampel A. Hirsch J. Chem. Soc., Perkin Trans. 2 1998 6 1471 1478
48. S.-J. Yan Y.-Y. Yan Y.-M. Li M.-J. Xie J. Lin Acta Crystallogr., Sect. E 2007 63 o2944
49. M. K. Rauf A. Bashah M. Bolte Acta Crystallogr., Sect. E 2006 62 o1859
50. B. Q. Su Acta Crystallogr., Sect. E 2005 61 o3492
51. L. Chen H.-B. Song Q.-M. Wang R.-Q. Huang J. Shang C.-H. Mao Acta Crystallogr., Sect. E 2004 60 o1865
52. B. M. Yamin A. S. Mardi Acta Crystallogr., Sect. E 2003 59 o399
53. A. L. Spek J. Appl. Crystallogr. 2003 36 7
54. A. Altomare G. Cascarano G. Giacovazzo A. Guagliardi M. C. Burla G. Polidori M. Camalli M. J. Appl. Crystallogr. 1994 27 435
55. D. J. Watkin, C. K. Prout, R. J. Carruthers and P. Betteridge, CRYSTALS, Chemical Crystallography Laboratory, Oxford, UK, 1996, p. 10
56. All UV/Vis experiments were performed in dichloromethane at room temperature (∼298 K) by adding aliquots of an anion stock solution to a receptor solution. The recorded sets of the absorption spectra were globally analyzed using the Specfit program (v. 3.0, Spectrum Software Associates) to get the corresponding absorption spectra of complexes and binding constants
57. K. Lang P. Curinová M. Dudic P. Prosková I. Stibor V. Stastny P. Lhoták Tetrahedron Lett. 2005 46 4469