Conical intersections in molecular photochemistry: The phase-change approach

Advances in Chemical Physics

Volumn 124, Issue , 2002, Pages 433-504

  Haas, Yehuda ^a   Zilberg, Shmuel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000907429     PISSN: 00652385     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (150)

1. E. Teller, J. Phys. Chem. 41, 109 (1937).
2. M. Klessinger and J. Michl, Excited States and Photochemistry of Organic Molecules, VCH, New York, 1995.
3. W. Fuss, S. Lochbrunner, A. M. Müller, T. Schikarski, W. E. Schmid, and S. A. Trushin Chem. Phys. 232, 161 (1998).
4. E. W.-G. Diau, S. De Feyter, and A. H. Zewail J. Chem. Phys. 110, 9785 (1999).
5. J. M. Metsdagh, J. P. Visicot, M. Elhanine, and B. Soep, J. Chem. Phys. 113, 237 (2000).
6. I. Ohmine, J. Chem. Phys. 83, 2348 (1985).
7. A. L. Sobolewski and W. Domcke, Chem. Phys. 259, 181 (2001).
8. M. Klessinger, Angew. Chem. Int. Ed. Engl. 34, 549 (1995).
9. F. Bernardi, M. A. Robb, and M. Olivucci, Chem. Soc. Rev. 25, 321 (1996).
10. M. Ben-Nun and T. J. Martinez,, Chem. Phys. 259, 237 (2001).
11. D. R. Yarkoni, Rev. Modern Phys. 68, 985 (1996).
12. G. Herzberg and H. C. Longuet-Higgins, Discuss. Faraday Soc. 35, 77 (1963).
13. H. C. Longuet-Higgins, Proc. Roy. Soc London Ser. A 344, 147 (1975).
14. G. N. Lewis, J. Am. Chem. Soc. 38, 762 (1916).
15. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca, N.Y., 1940.
16. R. P. Feynmann, M. Leighton, and M. Sands, The Feynmann Lectures in Physics, Vol. III, Addison-Wesley, Reading, MA, 1965, Chapters 9 and 10.
17. M. G. Evans and E. Warhurst, Trans. Faraday Soc. 34, 614 (1938).
18. M. G. Evans, Trans. Faraday Soc. 35, 824 (1939).
19. M. J. S. Dewar, The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill, New York, 1969.
20. H. E. Zimmerman, J. Am. Chem. Soc. 88, 1564,1566 (1966).
21. H. E. Zimmerman, Acc. Chem. Res. 4, 272 (1971).
22. W. A. III, Goddard, J. Am. Chem. Soc. 94, 793 (1972).
23. G. Levin and W. A. III, Goddard, J. Am. Chem. Soc. 97, 1649 (1975).
24. A. F. Voter and W. A. III, Goddard, Chem. Phys. 57, 253 (1981).
25. S. Zilberg and Y. Haas, J. Photochem. Photobiol. 144, 221 (2001).
26. S. S. Shaik, J. Am. Chem. Soc. 103, 3692 (1981).
27. S. Shaik and P. C. Hiberty, Adv. Quantum. Chem. 26, 99 (1995).
28. S. Shaik, S. Zilberg, and Y. Haas, Acc. Chem. Res. 29, 211 (1996).
29. S. Zilberg and Y. Haas, Int. J. Quant. Chem. 71, 133 (1999).
30. E. Hückel, Z. Phys. 70, 204 (1931).
31. L. Salem, Electrons in Chemical Reactions: First Principles, John Wiley & Sons, Inc., New York, 1982.
32. W. J. van der Hart, J. J. Mulder, and L. J. Oosterhoff, J. Am. Chem. Soc. 94, 5724 (1972).
33. J. J. Mulder and L. J. Oosterhoff, Chem Commun. 305, 307 (1970).
34. S. S. Xantheas, G. J. Atchity, S. T. Elbert, and K. Ruedenberg, J. Chem. Phys. 94, 8054 (1991).
35. W. Gerhartz, R. D. Poshusta, and J. Michl, J. Am. Chem. Soc. 98, 6427 (1977); 99, 4263 (1976).
36. A. J. Stone, Proc. R. Soc Lond. Ser. A 351, 141 (1976).
37. S. Glasstone, K. J. Laidler, and H. Eyring, The Theory of Rate Processes, McGraw-Hill, New York, 1941.
38. For a review of the method, see M. A. Robb, M. Garavelli, M. Olivucci, and F. Bernardi, in Reviews in Computational Chemistry, K. B. Lipkovwitz and D. B. Boyd, eds., Wiley-VCH, New York, 2000, Vol. 15, pp. 87-212.
39. P. Celani, M. Garavelli, S. Ottani, F. Bernardi, M. A. Robb, and M. Olivucci, J. Am. Chem. Soc. 117, 11584 (1995).
40. A. F. Voter and W. A., Goddard, J. Am. Chem. Soc. 108, 2830 (1986).
41. S. Zilberg and Y. Haas, Eur. J. Chem. 5, 1755 (1999).
42. S. Zilberg and Y. Haas, Chem. Phys. 259, 249 (2000).
43. M. J. S. Dewar, Tetrahedron Suppl. 8, Part 1, 75 (1966).
44. M. J. S. Dewar, Angew. Chem. Int. Ed. Engl. 10, 761 (1971).
45. M. A. Robb and F. Bernardi, in J. Bertran and I. G. Csizmadia, eds., New Theoretical Concepts for Understanding Organic Reactions, Kluwer, N.Y., 1989, p. 101.
46. E. Heilbronner, Tetrahedron Lett. 1923 (1964).
47. D. P. Craig, J. Chem. Soc. 997, (1959).
48. W. T. A. M. van der Lugt, and L. J. Oosterhoff, J. Am. Chem. Soc. 91, 6042 (1969)
49. Chem. Commun. 1235 (1968)
50. Mol. Phys. 18, 177 (1970).
51. W. Fuss, Y. Haas, and S. Zilberg, Chem. Phys. 259, 273 (2000).
52. S. Zilberg and Y. Haas, J. Phys. Chem. A 103, 2364 (1999).
53. S. C. Wright, D. L. Cooper, J. Gerratt, and M. Raimondi, J. Phys. Chem. 96, 7943 (1992)
54. P. B. Karadakov, D. L. Cooper, J. Gerratt, and M. Raimondi, J. Phys. Chem. 99, 10186 (1995).
55. S. Zilberg, Y. Haas, D. Danovich, and S. Shaik, Angew. Chem. Int. Ed. Engl. 37, 1394 (1998).
56. R. B. Woodward and R. Hoffmann, Angew. Chem. Int. Ed. Engl. 8, 781 (1969).
57. H. C. Longuet-Higgins and E. W. Abramson, J. Am. Chem. Soc. 87, 2045 (1965).
58. D. M. Silver, J. Am. Chem. Soc. 96, 5959 (1974).
59. H. E. Zimmerman, Acc. Chem. Res. 5, 393 (1972).
60. F. Merlet, S. D. Peyerimhoff, T. J. Bunker, and S. Shih, J. Am. Chem. Soc. 96, 959 (1974)
61. M. Yamaguchi, J. Mol. Struct. (THEOCHEM) 365, 145 (1996).
62. J. J. C. Mulder, Nouv. J. Chim. 4, 283 (1980).
63. G. J. Collin, Adv. Photochem. 14, 135 (1987).
64. R. Hoffmann, R.W. Alder, and C. F.Wolicox, J. Am. Chem. Soc. 92, 4992 (1970);
65. M. S. Gordon and M. W. Schmidt, J. Am. Chem. Soc. 115, 7486 (1993).
66. R. Srinivasan, L. S. White, A. R. Rossi, and G. A. Epling, J. Am. Chem. Soc. 103, 7299 (1981).
67. E. V. Cromwell, D.-J. Liu, M. J. J. Vrakking, A. H, Kung, and Y. T. Lee, J. Chem. Phys. 92, 3230 (1990).
68. E. V. Cromwell, D.-J. Liu, M. J. J. Vrakking, A. H. Kung, and Y. T. Lee, J. Chem. Phys. 95, 297 (1991).
69. A. Kumar, P. K. Chowdhury, K. V. S. R. Rao, and J. P. Mittal, Chem. Phys. Lett. 182, 165 (1991)
70. A. Kumar, P. D. Naik, R. D. Sainy, and J. P. Mittal, Chem. Phys. Lett. 309, 191 (1999).
71. S. De Feyter, E. W.- G. Diau, and A. H. Zewail, PCC 2, 877 (2000).
72. S. Wilsey and K. N. Houk, J. Am. Chem. Soc. 122, 2651 (2000).
73. S. S. Hixson, P. S. Mariano, and H. E. Zimmerman, Chem. Rev. 73, 531 (1973).
74. R. J. Rico, M. Page, and C. Doubleday, Jr., J. Am. Chem. Soc. 114, 1131 (1992).
75. M. J. S. Dewar, Adv. Chem. Phys. 8, 121 (1965).
76. H. A. Jahn and E. Teller, Proc. R. Soc. London Ser. A 161, 220 (1937).
77. I. B. Bersuker, Chem. Rev. 101, 1067 (2001).
78. I. B. Bersuker and V. Z. Pollinger, Vibronic Interactions in Molecules and Crystals, Springer, New York, 1996.
79. W. T. Borden and E. R. Davidson, J. Am. Chem. Soc. 101, 3771 (1979).
80. B. E. Applegate, T. A. Miller, and T. A. Barckholz, J. Chem. Phys. 114, 4855 (2001).
81. G. R. Liebling and H. M. McConnel, J. Chem. Phys. 42, 3931 (1965).
82. H. Fischer and J. N. Murrell, Theor. Chim. Acta (Berl.) 1, 463 (1967).
83. B. E. Applegate, A. J. Bezant, and T. A. Miller, J. Chem. Phys. 114, 4869 (2001).
84. E. P. F. Lee and T. G. Wright, PCCP 1, 219 (1999).
85. J. W. Zwanziger and E. R. Grant, J. Chem. Phys. 87, 2954 (1987).
86. B. A. Williams and T. A. Cool, J. Chem Phys. 94, 6358 (1991).
87. L. Serrano-Anders, M. Merchan, I. Nebot-Gil, R. Lindh, and B. O. Roos, J. Chem. Phys. 98, 3151 (1993).
88. We are indebted to Professor T. Martinez for a discussion on this point.
89. V. Bonacic-Koutecky, P. Bruckmann, P. Hiberty, J. Koutecky, C. Leforestier, and L. Salem, Angew. Chem. Int. Ed. Engl. 14, 575 (1975).
90. Y. Haas and U. Samuni, Prog. React. Kinet. 23, 211 (1998).
91. Y. Inoue, Chem. Rev. 92, 741 (1992).
92. M. Squillacote and T. C. Semple, J. Am. Chem. Soc. 112, 5546 (1990).
93. G. Maier, Angew. Chem. Int. Ed. Engl. 27, 309 (1988).
94. We are indebted to Professor Bernhard Dick for drawing our attention to these results, and for an enlightening discussion.
95. Y. Inoui, S. Takamuku, and H. Sakurai, J. Chem. Soc, Perkin Trans 2, 1635 (1977).
96. F. Bernardi, M. Olivucci, M. A. Robb, and G. Tonachini, J. Am. Chem. Soc. 114, 5805 (1992).
97. A. Gilbert and J. Baggott, Essentials of Molecular Photochemisty, Blackwell, London, 1991.
98. E. A. Halevy, Orbital Symmetry and Reaction Mechanisms: The OCAMS View, Springer, Berlin, 1992.
99. I. J. Palmer, I. N. Ragazos, F. Bernardi, M. Olivucci, M. A. Robb, and G. Tonachini, J. Am. Chem. Soc. 115, 673 (1993)
100. A. L. Sobolewski, C. Woywood, and W. Domcke, J. Chem. Phys. 98, 5627 (1993);
101. J. Dreyer and M. Klessinger, Eur. J. Chem. 2, 335 (1996).
102. M. I. McCarthy, P. Rosmus, H.-J.Werner, P. Botschwina, and V. Vaida, J. Chem. Phys. 86, 6693 (1987).
103. D. R. Eaton, J. Am. Chem. Soc. 90, 4272 (1968);
104. T. H. Whitesides, J. Am. Chem. Soc. 91, 2395 (1969).
105. F. Scandola, O. Traverno, V. Balzani, G. L. Zucchini, and V. Carassity, Inorg. Chem. Acta. 1, 76 (1967).
106. J. K. Burdett, Inorg. Chem. 15, 212 (1976).
107. H. E. Zimmerman, and H. Iwamura, J. Am. Chem. Soc. 92, 2015 (1970).
108. 2 photogenerated in the isolated molecule," PCCP 4, 34 (2002).
109. M. Merchan, L. Serrano-Andres, L. S. Slater, B. O. Roos, R. McDiarmid, and X. Xing, J. Phys. Chem. A 103, 5468 (1999).
110. G. A. Worth and L. S. Cederbaum, Chem. Phys. Lett. 338, 219 (2001).
111. M. S. Berry, Proc. R. Soc. London, Ser. A. 392, 45 (1984).
112. S. Adhukari and G. D. Billing, Chem. Phys. 259, 149 (2000).
113. A. Kuppermann, in Dynamics of Molecules and Chemical Reactions, R. E. Wyatt and J. Z. H. Zhang, eds., Marcel Dekker, New York, 1996.
114. Y. Aharonov and D. Bohm, Phys. Rev. 115, 485 (1959).
115. C. A. Mead, Rev. Mod. Phys. 64, 51 (1992).
116. D. G. Truhlar, J. Chem. Phys. 70, 2282 (1979).
117. G. J. Atchity, K. Ruedenberg, and A. Nanayakkara, Theor. Chim. Acc. 96, 195 (1997).
118. D. R. Yarkoni, Acc. Chem. Res. 31, 511 (1998).
119. D. R. Yarkoni, Theor. Chem. Acc. 98, 197 (1997).
120. C. A. Mead, J. Chem. Phys. 78, 807 (1983).
121. H. Köppel, W. Domcke, and L. S. Cederbaum, Adv. Chem. Phys. 57, 59 (1984).
122. M. Baer, Chem. Phys. 259, 123 (2000).
123. A. Mebel, M. Baer, and S. H. Lin, J. Chem. Phys. 112, 10703 (2000).
124. F. Bernardi, M. Olivucci, and M. A. Robb, J. Am. Chem. Soc. 114, 1606 (1992).
125. M. J. Bearpark, M. A. Robb, and H. B. Schlegel, Chem. Phys. Lett. 223, 269 (1994).
126. M. Olivucci, F. Bernardi, and M. A. Robb, J. Am. Chem. Soc. 116, 2034 (1994).
127. M. Olivucci, I. N. Ragazos, F. Bernardi, and M. A. Robb, J. Am. Chem. Soc. 115, 3710 (1993).
128. W. Domcke and G. Stock, Adv. Chem. Phys. 100, 1 (1997).
129. F. Santoro, C. Petrongolo, G. Granucci, and M. Persico, Chem. Phys. 259, 193 (2000).
130. A. Ferretti, A. Lami, and G. Villani, Chem. Phys. 259, 201 (2000).
131. S. Mahapatra, H. Köppel, L. S. Cederbaum, P. Stampfuss, andW.Wenzel, Chem. Phys. 259, 211 (2000).
132. M. Ito and I. Ohmine, J. Chem. Phys. 106, 3159 (1997).
133. M. Ben-Nun, J. Quenneville, and T. M. Martinez, J. Phys. Chem. A 104, 5161 (2000).
134. C. Bornemann and M. Klessinger, Chem. Phys. 259, 263 (2000).
135. R. Izzo and M. Klessinger, J. Comput. Chem. 21, 52 (2000).
136. E. Havinga and J. Cornelisse, Pure Appl. Chem. 47, 1 (1976).
137. N. J. Turro, Modern Molecular Photochemistry, Bejamin/Cummings, Menlo Park, CA, 1978.
138. D. I. Schuster, G. Lem, and N. A. Kaprinidis, Chem. Rev. 93, 3 (1991).
139. J. Michl, Photochem. Photobiol. 25, 141 (1977).
140. L. Salem and C. Rowland, Angew. Chem. Int. Ed. Engl. 11, 92 (1972).
141. L. Salem, Science. 191, 822 (1976).
142. J. A. Berson, Acc. Chem. Res. 11, 466 (1978).
143. J. Michl, Mol. Photochem. 4, 243-257 (1972).
144. J. Michl, Top. Curr. Chem. 46, 1 (1974).
145. J. Michl, in "Photochemical Reactions: Correlation Diagrams and Energy Barriers," G. Klopman, ed., Chemical Reactivity and Reaction Paths, John Wiley & Sons, Inc., New York, 1974.
146. J. Michl and V. Bonacic-Koutecky, Electronic Aspects of Organic Photochemistry, John Wiley & sons; Inc. New York, 1990.
147. L. Salem, J. Am. Chem. Soc. 96, 3486 (1974).
148. R. McWeeny and B. T. Sutcliffe, Methods of Molecular Quantum Mechanics, Academic Press, 1969, Chap. 6.
149. H. Eyring, J. Walter, and G. E. Kimball, Quantum Chemistry, John Wiley & Sons, Inc., New York, 1944, Chap. 13.
150. L. Pauling, J. Chem. Phys. 1, 280 (1933).