Water and hydrogen halides serve the same structural role in a series of 2+2 hydrogen-bonded dimers based on 2,6-bis(2-anilinoethynyl)pyridine sulfonamide receptors

Angewandte Chemie - International Edition

Volumn 47, Issue 1, 2008, Pages 117-120

  Berryman, Orion B ^a   Johnson II, Charles A ^a   Zakharov, Lev N ^a   Haley, Michael M ^a   Johnson, Darren W ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Anions; Dimers; Hydrogen bonds; Receptors; Self assembly

Indexed keywords

HYDROGEN; HYDROGEN BONDS; NEGATIVE IONS; SELF ASSEMBLY; WATER;

CL GREEN; HYDROGEN HALIDES;

DIMERS;

HALOGENATED HYDROCARBON; PYRIDINE DERIVATIVE; SULFONAMIDE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; HYDROCARBONS, HALOGENATED; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; SULFONAMIDES; WATER; X-RAY DIFFRACTION;

EID: 37549054036     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703971     Document Type: Article

References (34)

1. K. Liu, J. D. Cruzan, R. J. Saykally, Science 1996, 271, 929.
2. Y. M. Rhee, E. J. Sorin, G. Jayachandran, E. Lindahl, V. S. Pande, Proc. Natl. Acad. Sci. USA 2004, 101, 6456.
3. a) J. Friedman, Y. T. Meharenna, A. Wilks, T. L. Poulos, J. Biol. Chem. 2006, 282, 1066;
4. b) S. Nagano, T. L. Poulos, J. Biol. Chem. 2005, 280, 31659.
5. C. E. MacBeth, A. P. Golombek, V. G. Young, Jr., C. Yang, K. Kuczera, M. P. Hendrich, A. S. Borovik, Science 2000, 289, 938.
6. F. Hof, L. Trembleau, E. C. Ullrich, J. Rebek, Jr., Angew. Chem. 2003, 115, 3258;
7. Angew. Chem. Int. Ed. 2003, 42, 3150.
8. a) M. Yamanaka, A. Shivanyuk, J. Rebek, Jr., J. Am. Chem. Soc. 2004, 126, 2939;
9. b) L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469.
10. a) J. L. Atwood, L. J. Barbour, A. Jerga, Chem. Commun. 2001, 2376;
11. b) S. M. Biros, J. Rebek, Jr., Chem. Soc. Rev. 2007, 36, 93.
12. J. L. Sessler, P. A. Gale, W.-S. Cho, Anion Receptor Chemistry, Royal Society of Chemistry, Cambridge, 2006.
13. An understanding of the coordination preferences of anions is emerging, but the directionality is still less defined than for their cationic counterparts. For a detailed discussion, see : S. O. Kang, M. A. Hossain, K. Bowman-James, Coord. Chem. Rev. 2006, 250, 3038.
14. J. Sanchez-Quesada, C. Seel, P. Prados, J. de Mendoza, I. Dalcol, E. Giralt, J. Am. Chem. Soc. 1996, 118, 277.
15. R. Vilar, Angew. Chem. 2003, 115, 1498;
16. Angew. Chem. Int. Ed. 2003, 42, 1460.
17. a) P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light, M. B. Hursthouse, J. Am. Chem. Soc. 2002, 124, 11228;
18. b) K. A. Nielsen, W.-S. Cho, G. H. Sarova, B. M. Petersen, A. D. Bond, J. Becher, F. Jensen, D. M. Guldi, J. L. Sessler, J. O. Jeppesen, Angew. Chem. 2006, 118, 7002;
19. Angew. Chem. Int. Ed. 2006, 45, 6848;
20. c) S. J. Coles, J. G. Frey, P. A. Gale, M. B. Hursthouse, M. E. Light, K. Navakhun, G. L. Thomas, Chem. Commun. 2003, 568.
21. For an example of water and halides occupying the same binding sites in a protein, see: T. J. Fiedler, C. A. Davey, R. E. Fenna, J. Biol. Chem. 2000, 275, 11964.
22. a) C. A. Johnson II, Ph.D. Thesis, University of Oregon, 2007;
23. b) C. A. Johnson II, O. B. Berryman, M. J. Hynes, L. N. Zakharov, D. W. Johnson, M. M. Haley, unpublished result s.
24. W. B. Wan, M. M. Haley, J. Org. Chem. 2001, 66, 3893.
25. -3.
26. -3.
27. The "staggered" conformation for sulfonamides refers to the conformation in which the lone pair of the nitrogen atom bisects the O-S-O angle (the lone pair is antiperiplanar to the S-C bond), see: A. K. H. Hirsch, S. Lauw, P. Gersbach, W. B. Schweizer, F. Rohdich, W. Eisenreich, A. Bacher, F. Diederich, ChemMedChem 2007, 2, 806.
28. M. J. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311.
29. -.
30. -3.
31. 3.
32. - with halides exhibit a steep linear increase up to one equivalent of halide, with chloride affecting the steepest binding isotherm and iodide the shallowest. The second portion of the equilibrium exhibits a much smaller influence on the overall chemical shift of the complex. The second portion of the binding isotherm has made it difficult to determine association constants. Host-guest equilibria will be reported in due course.
33. Subsequent iterations of this experiment resulted in the formation of precipitate, suggesting that the first trial was supersaturated. The relatively low solubility of this complex in organic solvents has hindered further determination of association constants.
34. -3.