Helical water chains in aquapores of organic hexahost: Remarkable halogen-substitution effect on the handedness of water helix

Chemical Communications

Volumn , Issue 24, 2005, Pages 3024-3026

  Saha, Binoy K ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORINE DERIVATIVE; HALOGEN; PHLOROGLUCINOL DERIVATIVE; TRIBROMOPHLOROGLUCINOL; TRICHLOROPHLOROGLUCINOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; MOLECULAR INTERACTION; POROSITY;

EID: 21844479346     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500284b     Document Type: Article

References (35)

1. (a) R. Ludwig, Angew. Chem. Int. Ed., 2001, 40, 1808;
2. (b) R. Ludwig, Angew. Chem. Int. Ed., 2003, 42, 258;
3. (c) J. M. Ugalde, I. Alkorta and J. Elguero, Angew. Chem. Int. Ed., 2000, 39, 717;
4. (d) C. A. Jeffrey, An Introduction to Hydrogen Bonding, OUP, Oxford, 1997.
5. (a) G. M. Preston, T. P. Carroll, W. B. Guggino and P. Agre, Science, 1992, 256, 385;
6. (b) S. Cukierman, Biophy. J., 2000, 78, 1825;
7. (c) K. Mitsuoka, K. Murata, T. Walz, T. Hirai, P. Agre, J. B. Heymann, A. Engel and Y. Fujiyoshi, J. Struct. Biol., 1999, 128, 34;
8. (d) P. Agre, Angew. Chem. Int. Ed., 2004, 43, 4278.
9. (a) Y. Lee, T. Vogt, J. A. Hriljac, J. B. Parise, J. C. Hanson and S. J. Kim, Nature, 2002, 420, 485;
10. (b) Y. Lee, T. Vogt, J. A. Hriljac, J. B. Parise and G. Artioli, J. Am. Chem. Soc., 2002, 124, 5466;
11. (c) H. Birkedal, D. Schwarzenbach and P. Pattison, Angew. Chem. Int. Ed., 2002, 41, 754;
12. (d) G. Hummer, J. C. Rasaiah and J. P. Noworyta, Nature, 2001, 414, 188.
13. J. L. Atwood and J. W. Steed (Eds.), Encyclopedia of Supra-molecular Chemistry, Vols. 1-2, Marcel Dekker, New York, 2004.
14. (a) B.-Q. Ma, H.-L. Sun and S. Gao, Chem. Commun., 2004, 2220;
15. (b) P. Rodriguez-Cuamatzi, G. Vargas-Díaz and H. Höpfl, Angew. Chem. Int. Ed., 2004, 43, 3041;
16. (c) L. J. Harbour, G. W. Orr and J. L. Atwood, Nature, 1998, 393, 671;
17. (d) L. J. Barbour, G. W. Orr and J. L. Atwood, Chem. Commun., 2000, 859;
18. (e) J. L. Atwood, L. J. Barbour, T. J. Ness, C. L. Raston and P. L. Raston, J. Am. Chem. Soc., 2001, 123, 7192;
19. (f) C. Janiak, T. G. Scharmann and S. A. Mason, J. Am. Chem. Soc., 2002, 124, 14010;
20. (g) B.-Q. Ma, H.-L. Sun and S. Gao, Angew. Chem. Int. Ed., 2004, 43, 1374;
21. (h) S. K. Ghosh and P. K. Bharadwaj, Angew. Chem. Int. Ed., 2004, 43, 3577;
22. (i) K. Raghuraman, K. K. Katti, L. J. Barbour, N. Pillarsetty, C. L. Barnes and K. V. Katti, J. Am. Chem. Soc., 2003, 125, 6955;
23. (j) L. E. Cheruzel, M. S. Pometun, M. R. Cecil, M. S. Mashuta, R. J. Wittebort and R. M. Buchanan, Angew. Chem. Int. Ed., 2003, 42, 5452;
24. (k) A. Mukherjee, M. K. Saha, M. Nethaji and A. R. Chakravarty, Chem. Commun., 2004, 716;
25. (l) P. S. Sidhu, K. A. Udachin and J. A. Ripmeester, Chem. Commun., 2004, 1358;
26. (m) B. Sreenivasulu and J. J. Vittal, Angew. Chem. Int. Ed., 2004, 43, 5769.
27. L. Infantes and S. Motherwell, CrystEngComm, 2002, 4, 454.
28. A Piedfort Unit is the stacked dimer of two trigonal aromatic rings at van der Waals distance to form a hexagonal species. D. D. MacNicol and G. A. Downing, in Comprehensive Supramolecular Chemistry, Vol. 6, Solid-State Supramolecular Chemistry, Crystal Engineering, D. D. MacNicol, F. Toda and R. Bishop (Eds.), Pergamon, Oxford, 1996, pp. 42M64.
29. On the role on halogen atoms in lattice inclusion hosts, see B. K. Saha, R. K. R. Jetti, L. S. Reddy, S. Aitipamula and A. Nangia, Cryst. Growth. Des., 2005, 5, 887.
30. R. Baneriee, G. R. Desiraju, R. Mondal and J. A. K. Howard, Chem. Eur. J., 2004, 10, 3373.
31. The Br⋯Br contact of 3.29 Å is quite short. There are only 13 structures in the Cambridge Structural Database (CSD, http://www.ccdc.cam.ac. uk, July 2004 update, >300 000 entries) with Br⋯Br < 3.30 Å.
32. Two recent examples wherein weak halogen⋯halogen and halogen⋯oxygen interactions direct self-assembly in strongly hydrogen-bonded systems are: (a) J. N. Moorthy, R. Natarajan, P. Mal and P. Venugopalan, J. Am. Chem. Soc., 2002, 124, 6530;
33. (b) S. George, A. Nangia, C.-K. Lam, T. C. W. Mak and J.-F. Nicoud, Chem. Commun., 2004, 1202.
34. M. S. Pometun, U. M. Gundusharma, J. F. Richardson and R. J. Wittebort, J. Am. Chem. Soc., 2002, 124, 2345.
35. J. Bella, M. Eaton, B. Brodsky and H. M. Berman, Science, 1994, 266, 75.