Diastereoselectivity in the self-assembly of As2L 2Cl2 macrocycles is directed by the As-π interaction

Inorganic Chemistry

Volumn 46, Issue 22, 2007, Pages 9278-9284

  Cangelosi, Virginia M ^a   Sather, Aaron C ^a   Zakharov, Lev N ^a   Berryman, Orion B ^a   Johnson, Darren W ^a  

^a NONE

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EID: 34548513041     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701290h     Document Type: Article

References (27)

1. Healey, E. R.; Vickaryous, W. J.; Berryman, O. B.; Johnson, D. W. In Bottom-up Nanofabrication: Supramolecules, Self-Assemblies, and Organized Films; Nalwa, H. S., Ed.; American Scientific Publishers, 2007.
2. Pitt, M. A.; Johnson, D. W. Chem. Soc. Rev. 2007, 36, 1441-1453.
3. Cook, V. C.; Willis, A. C.; Zank, J.; Wild, S. B. Inorg. Chem. 2002, 41, 1897-1906.
4. Vickaryous, W. J.; Herges, R.; Johnson, D. W. Angew. Chem., Int. Ed. 2004, 43, 5831-5833.
5. Vickaryous, W. J.; Healey, E. R.; Berryman, O. B.; Johnson, D. W. Inorg. Chem. 2005, 44, 9247-9252.
6. The arsenic-π interaction is an attraction between a π base and a Lewis acidic arsenic center. For a more detailed discussion of the nature of these interactions in a supramolecular context, see: Carter, T. G., Vickaryous, W. J.; Cangelosi, V. M.; Johnson, D. W. Comm. Inorg. Chem. 2007, in press.
7. Schmidbaur, H.; Bublak, W.; Huber, B.; Muller, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 234-236.
8. Schmidbaur, H.; Nowak, R.; Steigelmann, O.; Muller, G. Chem. Ber. 1990, 123, 1221-1226.
9. Hamilton, T. D.; MacGillivray, L. R. Cryst. Growth Des. 2004, 4, 419-430.
10. Seeber, G. T., Bryan E. F.; Raymond, Kenneth N. In Top. Curr. Chem.; Springer Berlin: Heidelberg, Germany, 2006; Vol. 265, pp 147-183.
11. Beissel, T.; Powers, R. E.; Parac, T. N.; Raymond, K. N. J. Am. Chem. Soc. 1999, 121, 4200-4206.
12. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 349-358.
13. (a) Givens, R. S.; Venkatramanan, M. K.; Figard, J. Tetrahedron Lett. 1984, 25, 2187-2190.
14. (b) Givens, R. S.; Olsen, R. J.; Wylie, P. L. J. Org. Chem. 1979, 44, 1608-1613.
15. (c) Haenel, M. W. Chem. Ber. 1982, 115, 1425-1436.
16. 6 crystallizes out of benzene. Full details of the modeling of the disorder are contained in the Supporting Information.
17. Schmidbaur, H.; Bublak, W.; Huber, B.; Muller, G. Angew. Chem., Int. Ed. Engl. 1987, 99, 248.
18. Angew. Chem., Int. Ed. Engl. 1987, 26, 234-235.
19. This is similar to the established case of organic addition reactions, which can exhibit temperature dependent de's when the enthalpically and entropically favored products are not the same: Cainelli, G.; Giacomini, D.; Galletti, P. Eur. J. Org. Chem. 1999, 61-65.
20. Yamamoto, T.; Arif, A. M.; Stang, P. J. J. Am. Chem. Soc. 2003, 125, 12309-12317.
21. 3, (Nagase, S. The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds; Wiley: Chichester, U.K., 1994.)
22. and at least 42 kcal/mol for chiral arsines (Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Mackie, A. G.; Pritchard, R. B. In Chemistry of Arsenic, Antimony, and Bismuth; Norman, N. C., Ed.; Blackie Academic & Professional: London, 1998.).
23. Doak, G. O.; Freedman, L. D. Organometallic Compounds of Arsenic, Antimony, and Bismuth; Wiley Intersciences: New York, 1970.
24. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70-78.
25. Godfrey, S. M.; McAuliffe, C. A.; Mackie, A. G.; Pritchard, R. G. In Chemistry of Arsenic, Antimony, and Bismuth; Norman, N. C., Ed.; Blackie Academic & Professional: London, 1998, p 94.
26. Gutmann, V. Quart. Revs. 1956, 10, 451-462.
27. 2 macrocycles.