Pure C-H hydrogen bonding to chloride ions: A preorganized and rigid macrocyclic receptor

Angewandte Chemie - International Edition

Volumn 47, Issue 14, 2008, Pages 2649-2652

  Li, Yongjun ^a   Flood, Amar H ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Anions; Coordination chemistry; Hydrogen bonds; Macrocyclic ligands; Molecular modeling

Indexed keywords

HYDROGEN; HYDROGEN BONDS;

ANIONS; COORDINATION CHEMISTRY; MACROCYCLIC LIGANDS; MOLECULAR MODELING;

ELECTROLYSIS;

CHLORIDE; ION; MACROCYCLIC COMPOUND; ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TITRIMETRY;

CHLORIDES; HYDROGEN BONDING; IONS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; TITRIMETRY;

EID: 41949128097     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704717     Document Type: Article

References (45)

1. G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
2. a) Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, New York, 1997;
3. b) Special issue on 35 Years of Synthetic Anion Receptor Chemistry 1968-2003, see: Coord. Chem. Rev. 2003, 240, 1-221.
4. a) K. Bowman-James, Acc. Chem. Res. 2005, 38, 671-678;
5. b) P. A. Gale, R. Quesada, Coord. Chem. Rev. 2006, 250, 3219-3244.
6. C. A. Hunter, Angew. Chem. 2004, 116, 5424-5439;
7. Angew. Chem. Int. Ed. 2004, 43, 5310-5324.
8. K.-J. Chang, D. Moon, M. S. Lah, K.-S. Jeong, Angew. Chem. 2005, 117, 8140-8143;
9. Angew. Chem. Int. Ed. 2005, 44, 7926-7929.
10. I. Hisaki, S.-I. Sasaki, K. Hirose, Y. Tobe, Eur. J. Org. Chem. 2007, 607-615.
11. a) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573;
12. Angew. Chem. Int. Ed. 2006, 45, 1520-1543;
13. b) G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499.
14. a) K. A. Nielsen, W.-S. Cho, J. Lyskawa, E. Levillain, V. M. Lynch, J. L. Sessler, J. O. Jeppesen, J. Am. Chem. Soc. 2006, 128, 2444-2451;
15. b) H. Maeda, Y. Kusunose, Y. Mihashi, T. Mizoguchi, J. Org. Chem. 2007, 72, 2612-2616.
16. a) K. Chellappan, N. J. Singh, I.-C. Hwang, J. W. Lee, K. S. Kim, Angew. Chem. 2005, 117, 2959-2963;
17. Angew. Chem. Int. Ed. 2005, 44, 2899-2903;
18. b) N. Alhashimy, D. J. Brougham, J. Howarth, A. Farrell, B. Quilty, K. Nolan, Tetrahedron Lett. 2007, 48, 125-128.
19. a) G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565-573;
20. b) V. S. Bryantsev, B. P. Hay, J. Am. Chem. Soc. 2005, 127, 8282-8283.
21. For comparison, there are only two examples of wholly nonaromatic C-H⋯anion interactions, see: a) W. B. Farnham, D. C. Roe, D. A. Dixon, J. C. Calabrese, R. L. Marlow, J. Am. Chem. Soc. 1990, 112, 7707-7718;
22. b) S. S. Zhu, H. Staats, K. Brandhorst, J. Grunenberg, F. Gruppi, E. Dalcanale, A. Lützen, K. Rissanen, C. A. Schalley, Angew. Chem. Int. Ed. 2008, 47, 788-792.
23. D. J. Cram, Angew. Chem. 1988, 100, 1041-1052;
24. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020.
25. a) M. D. Best, S. L. Tobey, E. V. Anslyn, Coord. Chem. Rev. 2003, 240, 3-15;
26. b) C. A. Ilioudis, D. A. Tocher, J. W. Steed, J. Am. Chem. Soc. 2004, 126, 12395-12402.
27. a) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098;
28. b) S. Höger, Chem. Eur. J. 2004, 10, 1320-1329;
29. c) W. Zhang, J. S. Moore, Angew. Chem. 2006, 118, 4524-4548;
30. Angew. Chem. Int. Ed. 2006, 45, 4416-4439.
31. a) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711;
32. Angew. Chem. Int. Ed. 2002, 41, 2596-2599;
33. b) C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064;
34. c) W. S. Horne, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 126, 15366-15367;
35. d) K. D. Bodine, D. Y. Gin, M. S. Gin, J. Am. Chem. Soc. 2004, 126, 1638-1639;
36. e) Y. Angell, K. Burgess, J. Org. Chem. 2005, 70, 9595-9598.
37. a) Y. Li, J. C. Huffman, A. H. Flood, Chem. Commun. 2007, 2692-2694;
38. b) B. M. J. M. Suijkerbuijk, B. N. H. Aerts, H. P. Dijkstra, M. Lutz, A. L. Spek, G. van Koten, R. J. M. K. Gebbink, Dalton Trans. 2007, 1273-1276;
39. c) R. M. Meudtner, M. Ostermeier, R. Goddard, C. Limberg, S. Hecht, Chem. Eur. J. 2007, 13, 9834-9840.
40. Halide selectivity will be the topic of future studies.
41. L. Brammer, E. A. Bruton, P. Sherwood, Cryst. Growth Des. 2001, 1, 277-290.
42. Y. Miura, Y. Ushitani, K. Inui, Y. Teki, T. Takui, K. Itoh, Macromolecules 1993, 26, 3698-3701.
43. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
44. 5-H hydrogen.
45. M. H. Palmer, R. H. Findlay, A. J. Gaskell, J. Chem. Soc. Perkin Trans. 2 1974, 420-428.