Two significantly different conformations in crystal: formation of a molecular dimer governed by cation-π interactions

Tetrahedron Letters

Volumn 47, Issue 31, 2006, Pages 5557-5560

  Yamada, Shinji ^a   Morimoto, Yuka ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Cation interaction; Crystal structure; Molecular dimer; Pyridinium salt; Pyridinium interaction

Indexed keywords

BENZENE DERIVATIVE; CATION; DIMER; PYRIDINIUM DERIVATIVE;

ARTICLE; CONFORMATION; CRYSTAL; CRYSTAL STRUCTURE; DIMERIZATION; MOLECULAR INTERACTION;

EID: 33745276225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.144     Document Type: Article

References (25)

1. Gavezzotti A. Acc. Chem. Res. 27 (1994) 309
2. Dunitz J.D. Chem. Commun. (2003) 545
3. Braga D. Chem. Commun. (2003) 2751
4. For a review, see:. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303
5. Yamada S., and Morita C. J. Am. Chem. Soc. 124 (2002) 8184
6. Koizumi T., Tsutsui K., and Tanaka K. Eur. J. Org. Chem. (2003) 4528
7. Yamada S., Morita C., and Yamamoto J. Tetrahedron Lett. 45 (2004) 7475
8. Yamada S., Morimoto Y., and Misono T. Tetrahedron Lett. 46 (2005) 5673
9. Ishihara S., and Takeoka S. Tetrahedron Lett. 47 (2006) 181
10. Hunter C.A., Low C.M.R., Rotger C., Vinter J.G., and Zonta C. Proc. Natl. Acad. Sci. U.S.A. 90 (2002) 4873
11. Hunter C.A., Low C.M.R., Rotger C., Vinter J.G., and Zonta C. Chem. Commun. (2003) 834
12. Hunter C.A., Low C.M.R., Vinter J.G., and Zonta C. J. Am. Chem. Soc. 125 (2003) 9936
13. Heemstra J.M., and Moore J.S. J. Am. Chem. Soc. 126 (2004) 1648
14. Heemstra J.M., and Moore J.S. Chem. Commun. (2004) 1480
15. Heemstra J.M., and Moore J.S. Org. Lett. 6 (2004) 659
16. For a review, see:. Meyer E.A., Castellano R.K., and Diederich F. Angew. Chem., Int. Ed. 42 (2003) 1210
17. int = 0.0572). R1 = 0.0623 [I > 2s(I)], wR2 = 0.1925 (all data). CCDC 293709.
18. Yamada S., Misono T., and Tsuzuki S. J. Am. Chem. Soc. 126 (2004) 9862
19. -1.
20. int = 0.0716). R1 = 0.0833 [I > 2σ(I)], wR2 = 0.2287 (all data). CCDC 293710.
21. 3 solutions are as follows: The δ values for 1: H2, 10.78; H4, 9.01; H5, 7.88; H6, 8.66; The δ values for 2: H2, 10.87; H4, 8.98; H5, 7.94; H6, 8.51; The δ values for the reference compound: H2, 9.41; H4, 8.91; H5, 8.24; H6, 10.23.
22. For examples, see:. Sayers J., Schindler D., and Sundaralingam M. J. Am. Chem. Soc. 99 (1977) 3848
23. Denny B.J., Ringan N.S., Schwalbe C.H., Lambert P.A., Meek M.A., Griffin R.J., and Stevens M.F.G. J. Med. Chem. 35 (1992) 2315
24. Patel H.C., and Singh T.P. Acta Cryst. C46 (1990) 1061
25. Kumar S., Subramanian K., Schreurs A.M.M., Kroon J., and SteinKer T. J. Chem. Cryst. (2002) 411