Molecular tweezers as synthetic receptors: Molecular recognition of electron-deficient aromatic substrates by chemically bonded stationary phases

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 2741-2749

  Kamieth, Markus ^a   Burkert, Ulrich ^a   Corbin, Perry S ^b   Dell, Steven J ^b   Zimmerman, Steven C ^b   Klärner, Frank Gerrit ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Arene arene interactions; HPLC Bonded phases; Molecular recognition; Supramolecular chemistry

Indexed keywords

AROMATIC COMPOUND; BENZENE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; ENTHALPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032720810     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2741::aid-ejoc2741>3.0.co;2-k     Document Type: Article

References (50)

1. [1a] J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim 1995.
2. [1b] F. Vögtle, Supramolekulare Chemie, Teubner, Stuttgart, 1989.
3. [1c] F. Diederich, Supramolecular Chemistry, (Eds.: V. Balzani, L. De Cola), Kluwer, Dordrecht, 1992.
4. [2a] G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1994.
5. [2b] J. R. Fredericks, A. D. Hamilton, in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996.
6. T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 282-292.
7. [4a] C. Tanford, The Hydrophobic Effect, 2nd Ed., Wiley, New York, 1980.
8. [4b] J. T. Kellis, K. Nyberg, D. Sali, A. R. Fersht, Nature 1988, 333, 784-786.
9. [5a] C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534.
10. [5b] C. A. Hunter, Chem. Soc. Rev. 1994, 101-109.
11. [6a] F.-G. Klärner, J. Benkhoff, R. Boese, U. Burkert, M. Kamieth, U. Naatz, Angew. Chem. 1996, 108, 1195-1198; Angew. Chem. Int. Ed. Engl. 1996, 35, 1130-1133.
12. [6a] F.-G. Klärner, J. Benkhoff, R. Boese, U. Burkert, M. Kamieth, U. Naatz, Angew. Chem. 1996, 108, 1195-1198; Angew. Chem. Int. Ed. Engl. 1996, 35, 1130-1133.
13. [6b] F.-G. Klärner, U. Burkert, M. Kamieth, R. Boese, J. Benet-Buchholz, Chem. Eur. J. 1999, 5, 1700-1707.
14. [7a] S. C. Zimmerman, K. W. Saionz, Z. Zeng, Proc. Natl. Acad. Sci. USA 1993, 90, 1190-1193.
15. [7b] S. C. Zimmerman, K. W. Saionz, J. Am. Chem. Soc. 1995, 117, 1175-1176.
16. [7c] S. C. Zimmerman, W.-S. Kwan, Angew. Chem. 1995, 107, 2589-2592; Angew. Chem. Int. Ed. Engl. 1995, 34, 2404-2406. Review on chiral recognition by the use of CBSPs: W. H. Pirkle, T.C. Pochapsky, Chem. Rev. 1989, 89, 347-362.
17. [7c] S. C. Zimmerman, W.-S. Kwan, Angew. Chem. 1995, 107, 2589-2592; Angew. Chem. Int. Ed. Engl. 1995, 34, 2404-2406. Review on chiral recognition by the use of CBSPs: W. H. Pirkle, T.C. Pochapsky, Chem. Rev. 1989, 89, 347-362.
18. [7c] S. C. Zimmerman, W.-S. Kwan, Angew. Chem. 1995, 107, 2589-2592; Angew. Chem. Int. Ed. Engl. 1995, 34, 2404-2406. Review on chiral recognition by the use of CBSPs: W. H. Pirkle, T.C. Pochapsky, Chem. Rev. 1989, 89, 347-362.
19. [8a] J. Benkhoff, R. Boese, F.-G. Klärner, Liebigs Ann./Recueil 1997, 501-516.
20. [8b] J. Benkhoff, R. Boese, F.-G. Klärner, A. E. Wigger, Tetrahedron Lett. 1994, 35, 73-76.
21. W. H. Pirkle, T. C. Pochapsky, G. S. Mahler, D. E. Corey, D. S. Reno, D. M. Alessi, J. Org. Chem. 1986, 51, 4991-5000.
22. [10a] C. M. Lochmüller, M. T. Kersey, Anal. Chem. 1988, 60, 1910-1914.
23. [10b] C. M. Lochmüller, M. L. Hunnicutt, J. Phys. Chem. 1986, 90, 4318-4322.
24. W. H. Pirkle, J. T. Welch, J. Liq. Chromatogr. 1991, 14, 1-8.
25. F.-G. Klärner, U. Burkert, M. Kamieth, A. E. Wigger, unpub-lished results.
26. [13a] F. Diederich, D. B. Smithrud, E. M. Sanford, T. B. Wyman, S. B. Ferguson, D. R. Carcanague, I. Chao, K. N. Houk, Acta Chem. Scand. 1992, 46, 205-215.
27. [13b] J. C. Adrian Jr., C. S. Wilcox, J. Am. Chem. Soc. 1992, 114, 1398-1403.
28. [13c] D. A. Stauffer, R. E. Barrans, D. A. Dougherty, J. Org. Chem. 1990, 55, 2762-2767.
29. L. R. Snyder in Chromatography: Fundamentals and Applications of Chromatography and Related Differential Migration Methods, Journal of Chromatography Library, 5th edition, Elsevier, New York, 1992, vol. 51A, Chapter 1. It has been argued that the phase ratio Φ should only depend on the amount of stationary phase that can actually interact with the mobile phase, not the total amount of bulk phase, see: C. Horvath, H.-J. Lin, J. Chromatogr. 1978, 149, 43-70.
30. L. R. Snyder in Chromatography: Fundamentals and Applications of Chromatography and Related Differential Migration Methods, Journal of Chromatography Library, 5th edition, Elsevier, New York, 1992, vol. 51A, Chapter 1. It has been argued that the phase ratio Φ should only depend on the amount of stationary phase that can actually interact with the mobile phase, not the total amount of bulk phase, see: C. Horvath, H.-J. Lin, J. Chromatogr. 1978, 149, 43-70.
31. For potential difficulties in the interpretation of enthalpies of retention see: W. H. Pirkle, R. S. Readnour, Anal. Chem. 1991, 63, 16-20.
32. 4 and cyclohexane. Here the cyano-substituted analytes show nonspecific retention (0 < k′ < 1 at 298 K) on the reference column.
33. [17a] P. C. Sadek, P. W. Carr, R. M. Doherty, M. J. Kamlet, R. W. Taft, M. H. Abraham, Anal. Chem. 1985, 57, 2971-2978.
34. [17b] P. W. Carr, R. M. Doherty, M. J. Kamlet, R. W. Taft, W. Melander, C. Horvath, Anal. Chem. 1986, 58, 2674-2680.
35. [17c] J. H. Park, P. W. Carr, M. H. Abraham, R. W. Taft, R. M. Doherty, M. J. Kamlet, Chromatographia, 1988, 25, 373-381.
36. R. W. Taft, J.-L. M. Abboud, M. J. Kamlet, M. H. Abraham, J. Solution Chem. 1985, 14, 153-175.
37. W. J. Cheong, P. W. Carr, Anal. Chem. 1989, 61, 1524-1529.
38. [20a] M. J. Kamlet, J.-I. M. Abboud, M. H. Abraham, R. W. Taft, J. Org. Chem. 1983, 48, 2877-2887.
39. [20b] Y. Marcus, J. Solution Chem. 1991, 20, 929-942.
40. [20c] D. C. Leggert, J. Solution Chem. 1993, 22, 289-296.
41. [21a] M. J. Kamlet, R. M. Doherty, M. H. Abraham, Y. Marcus, R. W. Taft, J. Phys. Chem. 1988, 92, 5244-5255.
42. [21b] M. H. Abraham, J. C. McGowen, Chromatographia, 1987, 23, 243-246.
43. R. Foster, Organic Charge-Transfer Complexes, (Ed.: A. T. Blomquist), Academic Press, London, 1969. R. S. Mulliken, J. Phys. Chem. 1952, Ithaca 56, 801.
44. R. Foster, Organic Charge-Transfer Complexes, (Ed.: A. T. Blomquist), Academic Press, London, 1969. R. S. Mulliken, J. Phys. Chem. 1952, Ithaca 56, 801.
45. C. Horváth, W. Melander, I. Molnár, J. Chromatogr. 1976, 125, 129-156.
46. [24a] K. T. Chapman, W. C. Still, J. Am. Chem. Soc. 1989, 111, 3075-3077.
47. [6]
48. M. Kamieth, F.-G. Klärner, F. Diederich, Angew. Chem. 1998, 110, 3497-3500; Angew. Chem. Int. Ed. Engl. 1998, 37, 3303-3306.
49. M. Kamieth, F.-G. Klärner, F. Diederich, Angew. Chem. 1998, 110, 3497-3500; Angew. Chem. Int. Ed. Engl. 1998, 37, 3303-3306.
50. This method is similar to affinity chromatography, but does not require elutions with varying concentrations of competing receptor or ligand, thus allowing the simultaneous determination of binding parameters for multiple analytes with a single injection.