Xylylene formation from vibrationally hot cyclophanes: Specific dissociation rate constants of strained molecules

Journal of Physical Chemistry A

Volumn 106, Issue 10, 2002, Pages 2014-2019

  Hosoi, Yuriko ^a   Yatsuhashi, Tomoyuki ^a   Ohtakeyama, Ken ^a   Shimizu, Seiji ^a   Sakata, Yoshiteru ^b   Nakashima, Nobuaki ^a  

^a Osaka Prefecture University   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STATISTICAL REACTION THEORY;

AROMATIC HYDROCARBONS; CHEMICAL BONDS; EXCIMER LASERS; LASER BEAM EFFECTS; PHOTODISSOCIATION; PHOTOLYSIS; PHOTONS; STATISTICAL METHODS;

RATE CONSTANTS;

EID: 0037076137     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0120817     Document Type: Article

References (60)

1. Holbrook, K.A.; Pilling, M.J.; Robertson, S.H. Unimolecular Reactions; 2nd ed.; Wiley & Sons: New York, 1996.
2. Srinivasan, R.J. Am. Chem. Soc. 1962, 84, 3432, 4141. Thrush, B.A.; Zwolenik, J.J. Bull. Soc. Chim. Belg. 1962, 71,642.
3. Srinivasan, R.J. Am. Chem. Soc. 1962, 84, 3432, 4141. Thrush, B.A.; Zwolenik, J.J. Bull. Soc. Chim. Belg. 1962, 71,642.
4. (a) Hippler, H.; Schubert, V.; Wendelken, H.J.; Troe, J. Chem. Phys. Lett. 1981, 84, 253. Hippler, H.; Troe, J.; Wendelken, H.J. J. Chem. Phys. 1983, 78, 5351. Brand, U.; Hippler, H.; Lindemann, L.; Troe, J. J. Chem. Phys. 1990, 84, 6305.
5. (a) Hippler, H.; Schubert, V.; Wendelken, H.J.; Troe, J. Chem. Phys. Lett. 1981, 84, 253. Hippler, H.; Troe, J.; Wendelken, H.J. J. Chem. Phys. 1983, 78, 5351. Brand, U.; Hippler, H.; Lindemann, L.; Troe, J. J. Chem. Phys. 1990, 84, 6305.
6. (a) Hippler, H.; Schubert, V.; Wendelken, H.J.; Troe, J. Chem. Phys. Lett. 1981, 84, 253. Hippler, H.; Troe, J.; Wendelken, H.J. J. Chem. Phys. 1983, 78, 5351. Brand, U.; Hippler, H.; Lindemann, L.; Troe, J. J. Chem. Phys. 1990, 84, 6305.
7. (b) Ikeda, N.; Nakashima, N.; Yoshihara, K. J. Chem. Phys. 1985, 82, 5285. Shimada, T.; Ojima, Y.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Phys. Chem. 1992, 96, 6298. Shimada, T.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Chem. Phys. 1993, 98, 9218.
8. (b) Ikeda, N.; Nakashima, N.; Yoshihara, K. J. Chem. Phys. 1985, 82, 5285. Shimada, T.; Ojima, Y.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Phys. Chem. 1992, 96, 6298. Shimada, T.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Chem. Phys. 1993, 98, 9218.
9. (b) Ikeda, N.; Nakashima, N.; Yoshihara, K. J. Chem. Phys. 1985, 82, 5285. Shimada, T.; Ojima, Y.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Phys. Chem. 1992, 96, 6298. Shimada, T.; Nakashima, N.; Izawa, Y.; Yamanaka, C. J. Chem. Phys. 1993, 98, 9218.
10. (c) Park, J.; Bersohn, R.; Oref, I. J. Chem. Phys. 1990, 93, 5700. Fröchtenight, R.; Toennies, J.P. J. Photochem. Photobiol. A. 1994, 80, 67.
11. (c) Park, J.; Bersohn, R.; Oref, I. J. Chem. Phys. 1990, 93, 5700. Fröchtenight, R.; Toennies, J.P. J. Photochem. Photobiol. A. 1994, 80, 67.
12. Radloff, W.; Stert, V.; Freudenberg, T.; Hertel, I.V.; Jouvet, C.; Dedonger Lardeux, C.; Solgadi, D. Chem. Phys. Lett. 1997, 281, 20. Farmanara, P.; Steinkellner, O.; Wick, M.T.; Wittmann, M.; Korn, G.; Stert, V.; Radloff, W. J. Chem. Phys. 1999, 111, 6264.
13. Radloff, W.; Stert, V.; Freudenberg, T.; Hertel, I.V.; Jouvet, C.; Dedonger Lardeux, C.; Solgadi, D. Chem. Phys. Lett. 1997, 281, 20. Farmanara, P.; Steinkellner, O.; Wick, M.T.; Wittmann, M.; Korn, G.; Stert, V.; Radloff, W. J. Chem. Phys. 1999, 111, 6264.
14. Blank, D.A.; North, S.W.; Stranges, D.; Suits, A.G.; Lee, Y.T. J. Chem. Phys. 1997, 106, 539. Lin, J.J.; Hsu, T.C.; Hwang, D.W.; Lee, Y.T.; Yang, X. J. Chem. Phys. 1998, 109, 10719.
15. Blank, D.A.; North, S.W.; Stranges, D.; Suits, A.G.; Lee, Y.T. J. Chem. Phys. 1997, 106, 539. Lin, J.J.; Hsu, T.C.; Hwang, D.W.; Lee, Y.T.; Yang, X. J. Chem. Phys. 1998, 109, 10719.
16. (a) Nakashima, N.; Ikeda, N.; Yoshihara, K. J. Phys. Chem. 1988, 92, 2, 4389. Suzuki, T.; Ichimura, T.; Kusaba, M.; Nakashima, N. Chem. Phys. Lett. 1996, 263, 197. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 1095. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 10645. Yatsuahshi, T.; Akiho, T.; Nakashima, N. J. Am. Chem. Soc. 2001, 123, 10137.
17. (a) Nakashima, N.; Ikeda, N.; Yoshihara, K. J. Phys. Chem. 1988, 92, 2, 4389. Suzuki, T.; Ichimura, T.; Kusaba, M.; Nakashima, N. Chem. Phys. Lett. 1996, 263, 197. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 1095. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 10645. Yatsuahshi, T.; Akiho, T.; Nakashima, N. J. Am. Chem. Soc. 2001, 123, 10137.
18. (a) Nakashima, N.; Ikeda, N.; Yoshihara, K. J. Phys. Chem. 1988, 92, 2, 4389. Suzuki, T.; Ichimura, T.; Kusaba, M.; Nakashima, N. Chem. Phys. Lett. 1996, 263, 197. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 1095. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 10645. Yatsuahshi, T.; Akiho, T.; Nakashima, N. J. Am. Chem. Soc. 2001, 123, 10137.
19. (a) Nakashima, N.; Ikeda, N.; Yoshihara, K. J. Phys. Chem. 1988, 92, 2, 4389. Suzuki, T.; Ichimura, T.; Kusaba, M.; Nakashima, N. Chem. Phys. Lett. 1996, 263, 197. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 1095. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 10645. Yatsuahshi, T.; Akiho, T.; Nakashima, N. J. Am. Chem. Soc. 2001, 123, 10137.
20. (a) Nakashima, N.; Ikeda, N.; Yoshihara, K. J. Phys. Chem. 1988, 92, 2, 4389. Suzuki, T.; Ichimura, T.; Kusaba, M.; Nakashima, N. Chem. Phys. Lett. 1996, 263, 197. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 1095. Yatsuhashi, T.; Nakashima, N. J. Phys. Chem. A 2000, 104, 10645. Yatsuahshi, T.; Akiho, T.; Nakashima, N. J. Am. Chem. Soc. 2001, 123, 10137.
21. (b) Damm, M.; Hippler, H.; Troe, H. J. Chem. Phys. 1988, 88, 3564.
22. (c) Sevy, E.T.; Muyskens, M.A.; Rubin, S.M.; Flynn, G.W.; Muckerman, J.T. J. Chem. Phys. 2000, 112, 5829. Sevy, E.T.; Muyskens, M.A.; Lin, Z.; Flynn, G.W. J. Phys. Chem. A 2000, 104, 10538.
23. (c) Sevy, E.T.; Muyskens, M.A.; Rubin, S.M.; Flynn, G.W.; Muckerman, J.T. J. Chem. Phys. 2000, 112, 5829. Sevy, E.T.; Muyskens, M.A.; Lin, Z.; Flynn, G.W. J. Phys. Chem. A 2000, 104, 10538.
24. (d) Hassoon, S.; Snavely, D.L. J. Chem. Phys. 1992, 97, 9081.
25. Yatsuhashi, T.; Nakashima, N. Bull Chem. Soc. Jpn. 2001, 74, 579.
26. Liebman, J.F.; Greenberg, A. Chem. Rev. 1976, 76, 311. Greenberg, A.; Liebman, J.F. Strained Organic Molecules; Academic Press: New York, 1978.
27. Liebman, J.F.; Greenberg, A. Chem. Rev. 1976, 76, 311. Greenberg, A.; Liebman, J.F. Strained Organic Molecules; Academic Press: New York, 1978.
28. Shimizu, S.; Nakashima, N.; Sakata, Y. Chem. Phys. Lett. 1998, 284, 396.
29. Otubo, T.; Mizogami, S.; Otubo, I.; Tozuka, Z.; Sakagami, A.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1973, 46, 3519.
30. Similar arrangements were used as reported in Nakashima, N.; Ikeda, N.; Shimo, N.; Yoshihara, K. J. Chem. Phys. 1987, 87, 3471.
31. Allinger, N.L.; Da Rooge, M.A.; Hermann, R.B. J. Am. Chem. Soc. 1961, 83, 1974. Hefelfinger, D.T.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 4754.
32. Allinger, N.L.; Da Rooge, M.A.; Hermann, R.B. J. Am. Chem. Soc. 1961, 83, 1974. Hefelfinger, D.T.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 4754.
33. Migirdicyan, E.; Baudet, J. J. Am. Chem. Soc. 1975, 97, 7400. Lejeune, V.; Despres, A.; Migirdicyan, E. J. Phys. Chem. 1984, 88, 2719.
34. Migirdicyan, E.; Baudet, J. J. Am. Chem. Soc. 1975, 97, 7400. Lejeune, V.; Despres, A.; Migirdicyan, E. J. Phys. Chem. 1984, 88, 2719.
35. Ikeda, N.; Nakashima, N.; Yoshihara K. J. Am. Chem. Soc. 1985, 107, 3381. Wallington, T.J.; Egsgaard, H.; Nielsen, O.J.; Platz, J.; Sehested, J.; Stein, T. Chem. Phys. Lett. 1998, 290, 363.
36. Ikeda, N.; Nakashima, N.; Yoshihara K. J. Am. Chem. Soc. 1985, 107, 3381. Wallington, T.J.; Egsgaard, H.; Nielsen, O.J.; Platz, J.; Sehested, J.; Stein, T. Chem. Phys. Lett. 1998, 290, 363.
37. Two-photon dissociation of benzene by an ArF excimer laser was found. The details will be published elsewhere.
38. Helgeson, R.C.; Cram, D.J. J. Am. Chem. Soc. 1966, 88, 509.
39. Sorimachi, K.; Morita, T.; Shizuka, H. Bull. Chem. Soc. Jpn. 1974, 47, 987.
40. (a) Kaupp, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 442.
41. (b) Kaupp, G.; Teufel, E.; Hopf, H. Angew. Chem., Int. Ed. Engl. 1979, 18, 215.
42. (c) Ishikawa, S.; Nakamura, J.; Nagakura, S. Bull. Chem. Soc. Jpn. 1980, 53, 2476.
43. Nurmukhametov, R.N.; Ryzhakova, N.V.; Pebalk, A.V.; Kardash, I.E. Russ. J. Phys. Chem. 1994, 68, 641.
44. Chapman, O.L.; Tsou, U.E.; Johonson, J.W. J. Am. Chem. Soc. 1987, 109, 553.
45. Chapman, O.L.; Johnson, J.W.; McMahon, R.J.; West, P.R. J. Am. Chem. Soc. 1988, 110, 501.
46. Mariella, R.P.; Steinhauser, S.W.; Diebold, A.C. J. Vac. Sci. Technol. B 1987, 5, 1360.
47. Flynn, C.R.; Michl, J. J. Am. Chem. Soc. 1974, 96, 3280.
48. Chapman, O.L.; Tsou, U.E.; Johnson, J.W. J. Am. Chem. Soc. 1987, 109, 553.
49. Zhong-zhi, Y.; Kovac, B.; Heilbronner, E.; Eltamany, S.; Hopf, H. Helv. Chim. Acta 1981, 64, 1991.
50. Boschi, V.R.; Schmidt, W. Angew. Chem. 1973, 85, 408.; Koenig, T.; Turtle, M.; Wielesek, R.A. Tetrahedron Lett. 1974, 29, 2537.
51. Boschi, V.R.; Schmidt, W. Angew. Chem. 1973, 85, 408.; Koenig, T.; Turtle, M.; Wielesek, R.A. Tetrahedron Lett. 1974, 29, 2537.
52. Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitani, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346.
53. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.; Petersson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Laham, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Cioslowski, J.; Stefanov, B.B.; Nanayakkara, A.; Challacombe, M.; Peng, C.Y.; Ayala, P.Y.; Chen, W.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Binkley, J.S.; Defrees, D.J.; Baker, J.; Stewart, J.P.; Head-Gordon, M.; Gonzalez, C.; Pople, J.A. Gaussian 94, SGI-G94RevE. 1; Gaussian, Inc.: Pittsburgh, PA, 1995.
54. Hippler, H.; Troe, J. J. Phys. Chem. 1990, 94, 3803.
55. Nishiyama, K.; Sakiyama, N.; Seki, S.; Horita, H.; Otubo, T.; Misumi, S. Bull. Chem. Soc. Jpn. 1980, 53, 869.
56. Shieh, C.; McNally, D.; Boyd, R.H. Tetrahedron 1969, 25, 3653.
57. Luu, Von S.H.; Troe, J. Ber. Bunsen-Ges. Phys. Chem. 1974, 78, 766.
58. -1, respectively.
59. Tsai, S.; Kin, C.; Lee, Y.T.; Ni, C. J. Chem. Phys. 2000, 113, 67.
60. Fröchtenicht, R.; Toennies, J.P. J. Photochem. Photobiol. A 1994, 80, 67.