Increasing the heavy atom effect of xenon by adsorption to zeolites: Photolysis of 2,3-diazabicyclo[2.2.2]oct-2-ene

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9552-9556

  Anderson, Mark A ^a   Grissom, Charles B ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[2.2.2]OCTANE DERIVATIVE;

ARTICLE; ELECTRON SPIN RESONANCE; PHOTOLYSIS;

EID: 0029860852     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961546h     Document Type: Article

References (51)

1. (a) McGlynn, S. P.; Azumi, T.; Kinoshita, M. Molecular Spectroscopy of the Triplet State; Prentice-Hall: Engelwood Cliffs, 1969.
2. (b) Turro, N. J. Modern Molecular Photochemistry; Benjamin Cummings: Menlo Park, 1978.
3. (c) Koziar, J. C.; Cowan, D. O. Acc. Chem. Res. 1978, 11, 334.
4. (d) Khudyakov, I. V.; Serebrennikov, Y. A.; Turro, N. J. Chem. Rev. 1993, 93, 537.
5. (a) Horrocks, A. R.; Wilkinson, F. Proc. R. Soc., Ser. A 1968, 306, 257.
6. (b) Robinson, G. W. J. Mol. Spectrosc. 1961, 6, 58.
7. Burton, C. S.; Noyes, W. A., Jr. J. Chem. Phys. 1968, 49, 1705.
8. -1. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker Inc.: New York, 1993; p 339.
9. (a) Cheung, T. T. P.; Fu, C. M.; Wharry, S. J. Phys. Chem. 1988, 92, 5170.
10. (b) Ito, T.; Fraissard, J. J. Chem. Phys. 1982, 76, 5225.
11. Ito, T.; Fraissard, J. J. Chem. Soc., Faraday Trans, 1 1987, 83, 451.
12. (a) Ramamurthy, V.; Eaton, D. F.; Caspar, J. V. Acc. Chem. Res. 1992, 25, 299.
13. (b) Borecka, B.; Gunmundsdottir, A. D.; Olorsson, G.; Ramamurthy, V.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1994, 116, 10322.
14. Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; p 429.
15. Anderson, M. A.; Grissom, C. B. J. Am. Chem. Soc. 1995, 17, 5041.
16. (a) Carroll, F. A.; Quina, F. H. J. Am. Chem. Soc. 1972, 94, 6246.
17. (b) Carroll, F. A.; Quina, F. H. J. Am. Chem. Soc. 1976, 98, 1.
18. MacBeath, M. E.; Unger, I. Can. J. Chem. 1971, 49, 594.
19. Morgan, M. A.; Pimentel, G. C. J. Phys. Chem. 1989, 93, 3056.
20. (a) Tanaka, F.; Hirayama, S.; Shobatake, K. Chem. Phys. Lett. 1992, 195, 243.
21. (b) Calcaterra, L. T.; Schuster, D. I. J. Am. Chem. Soc. 1981, 103, 2460.
22. Solubility Data Series Vol. 2 Krypton, Xenon and Radon-Gas Solubilities; Clever, H. L., Ed.; Pergamon Press: New York, 1979; p 159.
23. Turro, N. J.; Cheng, C.; Abrams, L.; Corbin, D. R. J. Am. Chem. Soc. 1987, 109, 2449.
24. Kim, T.; Choi, Y. S.; Yoshihara, K. Chem. Phys. Lett. 1995, 247, 541.
25. (a) Engel, P. S.; Steel, C. Acc. Chem. Res. 1973, 6, 275.
26. (b) Clark, W. D. K.; Steel, C. J. Am. Chem. Soc. 1971, 93, 6347.
27. Engel, P. S.; Nalepa, C. J. Pure Appl. Chem. 1980, 52, 2621.
28. (a) Ramamurthy, V.; Caspar, J. V.; Eaton, D. F.; Kuo, E. W.; Corbin, D. R. J. Am. Chem. Soc. 1992, 114, 3882.
29. (b) Ramamurthy, V.; Corbin, D. R.; Kumar, C. V.; Turro, N. J. Tetrahedron Lett. 1990, 31, 47.
30. Ramamurthy, V.; Caspar, J. V.; Corbin, D. R.; Eaton, D. F. J. Photochem. Photobiol A 1989, 50, 157.
31. (a) Saliel, J.; Khalil, G. E.; Schange, K. Chem. Phys. Lett. 1980, 70, 233.
32. (b) Garner. H. J. Phys. Chem. 1989, 93, 1826.
33. (a) Ramamurthy, V.; Corbin, D. R.; Eaton, D. F. Tetrahedron Lett. 1989, 30, 5833.
34. (b) Garcia-Garibay, M. A.; Zhang, Z.; Zhang, Z. J. Am. Chem. Soc. 1991, 113, 6212.
35. Zhang, Z.; Turro, N. J. Tetrahedron Lett. 1987, 28, 5637.
36. Zhang, Z.; Turro, N. J. Tetrahedron Lett. 1989, 30, 3767.
37. (a) Ramamurthy, V.; Corbin, D. R.; Turro, N. J.; Sato, Y. Tetrahedron Lett. 1989, 30, 5829.
38. (b) Ramamurthy, V.; Sanderson, D. R. Tetrahedron Lett. 1992, 33, 2757.
39. Ramamurthy, V.; Corbin, D. R.; Johnston, L. J. J. Am. Chem. Soc. 1992, 114, 3870.
40. This estimation is based on the calculated size of DBO (4.62 Å × 4.28 Å × 3.05 Å) and the space available inside the NaY zeolite. DBO is not assumed to "stack" well.
41. (a) Engel, P. S.; Horsey, D. W.; Keys, D. E.; Nalepa, C. J.; Soltero, L. R. J. Am. Chem. Soc. 1983, 105, 7108.
42. (b) Edmunds, A. J. F.; Samuel, C. J. J. Chem. Soc., Perkins Trans, 1 1989, 1267.
43. Roberson, M.; Simons, J., University of Utah, personal communication.
44. (a) Cohen, S. G.; Zand, R. J. Am. Chem. Soc. 1962, 84, 586.
45. (b) Askani, R. Chem. Ber. 1965, 98, 2551.
46. Ramamurthy, V.; Sanderson, D. R.; Eaton, D. F. Photochem. Photobiol. 1992, 56, 297.
47. Considering the entropic driving forces that derive from the ratio of internal to external surface areas (1000-10000) and the enthalpic driving forces from the electronic interactions between guest molecules and the cations of the zeolites, we assume that the majority of the DBO is taken into the supercage and not adsorbed onto the outer surface.
48. (a) Turro, N. J.; Zhang, Z. In Photochemistry on Solid Surfaces; Anpo, M., Matsuura, T., Eds.; Elsevier: New York, 1989.
49. (b) Turro, N. J. Pure Appl. Chem. 1986, 58, 1219.
50. Suzuki, I.; Oki, S.; Namba, S. J. Catal 1986, 100, 219.
51. Engel, P. S.; Keys, D. E.; Kitamura, A. J. Am. Chem. Soc. 1985, 107, 4964.