Chemical insight from crystallographic disorder-structural studies of supramolecular photochemical systems. Part 2. The β-cyclodextrin-4,7-dimethylcoumarin inclusion complex: A new β-cyclodextrin dimer packing type, unanticipated photoproduct formation, and an examination of guest influence on β-CD dimer packing

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 6, 2000, Pages 1095-1103

  Brett, Tom J ^a   Alexander, Jennifer M ^a   Stezowski, John J ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLINE MATERIALS; CRYSTALLOGRAPHY; DIMERS; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; MOLECULES; NUMERICAL ANALYSIS; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS; SUPRAMOLECULAR CHEMISTRY;

CYCLODEXTRIN DIMER; CYCLODEXTRIN DIMETHYLCOUMARIN; SUPRAMOLECULAR PHOTOCHEMICAL SYSTEMS;

ORGANIC COMPOUNDS;

EID: 0034211791     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906041c     Document Type: Article

References (34)

1. Part 1, T. J. Brett, J. M. Alexander, J. L. Clark, Charles R. Ross, II, G. S. Harbison and J. J. Stezowski, Chem. Commun., 1999. 1275.
2. V. Ramamurthy and K. Venkatesan, Chem. Rev., 1987, 87, 433.
3. V. Ramamurthy, in Photoprocesses of Host-Guest Complexes in the Solid State, ed. V. Ramamurthy, VCH, New York, 1991, p. 303.
4. V. Ramamurthy, Tetrahedron, 1986, 42, 5753.
5. D. O. Cowan and R. L. Drisko, Elements of Organic Photochemistry, Plenum Press, New York, 1976.
6. K. Gnanaguru, N. Ramasubbu, K. Venkatesan and V. Ramamurthy, J. Org. Chem., 1985, 50, 2337. It should be noted that a few examples of non-topochemical photoproduct formation have been observed for derivatized coumarins. For examples, see ref. 6 and references cited therein.
7. J. N. Moorthy and K. Venkatesan, J. Org. Chem., 1991, 56, 6957.
8. K. Saigo, Prog. Polym. Sci., 1992, 17, 35.
9. Y. Chen and M. T. Shiao, Bull. Chem. Soc. Jpn., 1992, 65, 3423.
10. K. Saigo, K. Sekimoto, N. Yonezawa, F. Ishii and M. Hasegawa, Bull. Chem. Soc. Jpn., 1985, 58, 1006.
11. T. Bach, Synthesis, 1998, 683.
12. J. N. Moorthy, K. Venkatesan and R. G. Weiss, J. Org. Chem., 1992, 57, 3292.
13. M. D. Cohen and G. M. J. Schmidt, J. Chem. Soc., 1964, 1996.
14. M. D. Cohen, G. M. J. Schmidt and F. I. Sonntag, J. Chem. Soc., 1964, 2000.
15. G. M. J. Schmidt, J. Chem. Soc., 1964, 2014.
16. M. D. Cohen, Angew. Chem., Int. Ed. Engl., 1975, 14, 386.
17. T. J. Brett, S. Liu, P. Coppens and J. J. Stezowski, Chem. Commun., 1999, 551.
18. D. Mentzafos, I. M. Mavridis, G. LeBas and G. Tsoucaris, Acta Crystallogr., Sect. B, 1991, 47, 746.
19. S. Sethna and R. Phadke, Org. React. (N.Y.), 1953, 7, 1.
20. W. Kabsch, J. Appl. Crystallogr., 1988, 21, 916.
21. G. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, 1997.
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian98 (Revision A.3), Pittsburgh, PA, 1998.
23. B. H. Besler, J. Kenneth M. Merz and P. A. Kollman, J. Comput. Chem., 1990, 11, 431.
24. U. C. Singh and P. A. Kollman, J. Comput. Chem., 1984, 5, 129.
25. W. Saenger, Inclusion Compounds, ed. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, Academic Press, New York, 1984.
26. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290.
27. T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10146.
28. T. Steiner and W. Saenger, J. Am. Chem. Soc., 1993, 115, 4540.
29. T. Steiner, G. Koellner, K. Gessler and W. Saenger, J. Chem. Soc., Chem. Commun., 1995, 511.
30. T. Steiner and W. Saenger, J. Chem. Soc., Chem. Commun., 1995, 2087.
31. G. R. Desiraju, Acc. Chem. Res., 1996, 29, 441.
32. This lab, unpublished results. It should be noted that the mode of inclusion is quite different for coumarin, which forms a 3:2 H-G complex (see ref. 1). The rest are assumed to be 2:2 H-G complexes because of spatial contraints and analysis of other complexes.
33. I. M. Mavridis and E. Hadjoudis, Carbohydr. Res., 1992, 229, 1.
34. A. Rontoyianni, I. M. Mavridis, E. Hadjoudis and A. J. M. Duisenberg, Carbohydr. Res., 1994, 252, 19.