Chemistry in motion - Off the MEP

Tetrahedron Letters

Volumn 56, Issue 50, 2015, Pages 6931-6943

  Rehbein, Julia ^a   Wulff, Bastian ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Mechanistic studies; Non statistical dynamics; Physical organic chemistry; Post transition state bifurcations; Reaction dynamics; Roaming

Indexed keywords

CARPENTER; CHEMICAL REACTION; CHEMISTRY; CONFORMATIONAL TRANSITION; HEIGHT; HUMAN; MODEL; MOTION; REACTION ANALYSIS; STATISTICAL MODEL; THEORETICAL MODEL;

EID: 84947602147     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.10.092     Document Type: Review

References (120)

1. H. Eyring J. Chem. Phys. 3 1935 107
2. H. Pelzer, and E. Wigner Z. Phys. Chem. B 15 1932 445
3. E.P. Wigner Trans. Faraday Soc. 34 1938 29
4. Tunneling is covered by variational TST: D.G. Truhlar, and B.C. Garrett Ann. Rev. Phys. Chem. 35 1984 159
5. W. Forst Unimolecular Reactions 2003 Cambridge University Press Cambridge
6. Selected examples by Hase et al.: J.G. López, G. Vayner, U. Lourderaj, S.V. Addepalli, S. Kato, W.A. deJong, T.L. Windus, and W.L. Hase J. Am. Chem. Soc. 129 2007 9976
7. C. Doubleday, G. Li, and W.L. Hase Phys. Chem. Chem. Phys. 4 2002 304 and also see citations 8,15.
8. B.K. Carpenter Acc. Chem. Res. 25 1992 520
9. B.K. Carpenter R.A. Moss, M.S. Platz, M. Jones Jr. Reactive Intermediate Chemistry 2004 Wiley New York 925
10. B.K. Carpenter Annu. Rev. Phys. Chem. 56 2005 57
11. 20,42,74,75
12. G. Jiménez-Osés, P. Liu, R.A. Matute, and K.N. Houk Angew. Chem., Int. Ed. 53 2014 8664
13. C.E. Doubleday, C.P. Suhrada, and K.N. Houk J. Am. Chem. Soc. 128 2006 90 and also see citations 16,17,19,36.
14. T. Baer, and W.L. Hase Unimolecular Reaction Dynamics 1996 Oxford University Press New York
15. M. Brouard, and C. Vallance Tutorials in Molecular Reaction Dynamics 2012 RSC Publishing
16. D.M. Birney Curr. Org. Chem. 14 2010 1658
17. H. Yamataka Adv. Phys. Org. Chem. 44 2010 173
18. S.J. Klippenstein, V.S. Pande, and D.G. Truhlar J. Am. Chem. Soc. 136 2014 528
19. P.R. Schreiner, H.P. Reisenauer, D. Ley, D. Gerbig, C.-H. Wu, and W.A. Allen Science 332 2011 1300
20. D.H. Ess, S.E. Wheeler, R.G. Iafe, L. Xu, N. Çelebi-Ölçüm, and K.N. Houk Angew. Chem., Int. Ed. 47 2008 7592
21. J. Rehbein, and B.K. Carpenter Phys. Chem. Chem. Phys. 13 2011 20906
22. For example NDEs have been described in the hydroboration: by Y. Oyla, and D.A. Singleton J. Am. Chem. Soc. 131 2009 3130 and nucleophilic substitutions
23. X.S. Bogle, and D.A. Singleton Org. Lett. 14 2012 2528
24. J. Mikosch, S. Trippel, C. Eichhorn, R. Otto, U. Lourderaj, J.X. Zhang, W.L. Hase, M. Weidemüller, and R. Wester Science 319 2008 183
25. L. Sun, K. Song, and W.L. Hase Science 296 2002 875
26. Wittig reaction: Z. Chen, Nieves-Quinones, J.R. Waas, and D.A. Singleton J. Am. Chem. Soc. 136 2014 13122
27. Selected examples for dynamics effects: in cyclopropanation reactions with singlet carbenes by D.C. Merrer, and P.R. Rablen J. Org. Chem. 70 2005 1630
28. L. Xu, C.E. Doubledy, and K.N. Houk J. Am. Chem. Soc. 132 2009 3029
29. L. Xu, C.E. Doubleday, and K.N. Houk J. Am. Chem. Soc. 133 2011 17848
30. in [2+2]-cycloaddition: O.M. Gonzales-James, E.E. Kwan, and D.A. Singleton J. Am. Chem. Soc. 134 2012 1914
31. in 1,3-dipolar cycloadditions: L. Xu, C.E. Doubleday, and K.N. Houk Angew. Chem., Int. Ed. 48 2009 2746
32. L. Xu, C.E. Doubleday, and K.N. Houk J. Am. Chem. Soc. 132 2010 3029
33. Z. Wand, J.S. Hirschi, and D.A. Singleton Angew. Chem. 121 2009 9320 Angew. Chem. Int. Ed. 2009, 48, 9156.
34. K. Black, P. Liu, L. Xu, C. Doubleday, and K.N. Houk PNAS 109 2012 12860
35. L. Törk, G. Jiménez-Osès, C. Doubleday, F. Liu, and K.N. Houk J. Am. Chem. Soc. 137 2015 4749
36. For an example see: C. Doubleday, C.P. Suhrada, and K.N. Houk J. Am. Chem. Soc. 128 2006 90
37. For an example see: J.A. Nummela, and B.K. Carpenter J. Am. Chem. Soc. 124 2002 8512
38. For an example: ozonolysis reaction L.M.M. Quijano, and D.A. Singleton J. Am. Chem. Soc. 133 2011 13824
39. W. Quapp, M. Hirsch, and D. Heidrich Theor. Chem. Acc. 100 1998 285
40. W. Quapp J. Mol. Struct. 695 2004 95
41. G.N. Sastry, and S. Shaik J. Am. Chem. Soc. 117 1995 3290
42. Subsequent studies: G.N. Sastry, and S. Shaik J. Phys. Chem. 100 1996 12241
43. S. Shaik, D. Danovich, G.N. Sastry, P.Y. Ayala, and H.B. Schlegel J. Am. Chem. Soc. 119 1997 9237
44. 72,73
45. T. Katori, S. Itoh, M. Sato, and H. Yamataka J. Am. Chem. Soc. 132 2010 3413
46. R. Akimoto, T. Tokugawa, Y. Yamamoto, and H. Yamataka J. Org. Chem. 77 2012 4073
47. Y. Yamamoto, H. Hasegawa, and H. Yamataka J. Org. Chem. 76 2011 4652
48. Reprinted with permission from H. Yamataka, M. Sato, H. Hasegawa, and S.C. Ammal Faraday Discuss. 145 2010 327
49. S. Itoh, N. Yoshimura, M. Sato, and H. Yamataka J. Org. Chem. 76 2011 8294
50. K. Tagawa, K. Sasagawa, K. Wakisaka, S. Monjiyama, M. Katayama, and H. Yamataka Bull. Chem. Soc. Jpn. 87 2014 119
51. M. Katayama, K. Sasagawa, and H. Yamataka J. Phys. Org. Chem. 25 2012 680
52. Reprinted with permission from S. Itoh, N. Yoshimura, M. Sato, and H. Yamataka J. Org. Chem. 76 2011 4652
53. An important publication in this context that emphasizes the need for combined experimental and computational approaches due to the still existing limitations in computational chemistry especially in predicting free energies is the following: R.E. Plata, and D.A. Singleton J. Am. Chem. Soc. 137 2015 3811
54. Reprinted with permission from D.C. Merrer, and P.R. Rablen J. Org. Chem. 70 2005 1630
55. B.K. Carpenter Chem. Rev. 113 2013 7265
56. L. Toma, S. Romano, P. Quadrelli, and P. Caramella Tetrahedron Lett. 42 2001 5077
57. P. Caramella, P. Quadrelli, and T. Lucio J. Am. Chem. Soc. 124 2002 1130
58. D.A. Singleton, C. Hang, M.J. Szymanski, M.P. Meyer, A.G. Leach, K.T. Kuwata, J.S. Chen, A. Greer, C.S. Foote, and K.N. Houk J. Am. Chem. Soc. 125 2003 1319
59. I.L. Andujar-D Sanctis, and D.A. Singleton Org. Lett. 14 2012 5238
60. Reprinted with permission from P. Caramella, P. Quadrelli, and T. Lucio J. Am. Chem. Soc. 124 2002 1130
61. See for example: M. Hamaguchi, M. Nakaishi, T. Nagai, T. Nakamura, and M. Abe J. Am. Chem. Soc. 129 2007 12981
62. B.K. Carpenter Angew. Chem., Int. Ed. 37 1998 3341
63. B.K. Carpenter J. Phys. Org. Chem. 16 2003 858
64. M.B. Reyes, and B.K. Carpenter J. Am. Chem. Soc. 120 1998 1641
65. M.B. Reyes, and B.K. Carpenter J. Am. Chem. Soc. 122 2000 10163
66. Reprinted with permission from B.K. Carpenter Chem. Rev. 113 2013 7265
67. D.R. Glowacki, C.H. Liang, S.P. Marsden, J.N. Harvey, and M.J. Pilling J. Am. Chem. Soc. 132 2010 13621
68. J. Zheng, E. Papajak, and D.G. Truhlar J. Am. Chem. Soc. 131 2009 15754
69. D. Samanta, A. Rana, and M. Schmittel J. Org. Chem. 79 2014 2368
70. Reprinted with permission from D. Samanta, A. Rana, and M. Schmittel J. Org. Chem. 79 2014 2368
71. Selected reviews J.M. Bowman, and A.G. Suits Phys. Today 64 2011 33
72. J.M. Bowman, and B.C. Shepler Annu. Rev. Phys. Chem. 62 2011 531
73. A.G. Suits Acc. Chem. Res. 41 2008 873
74. D. Townsend, S.A. Lahankar, S.K. Lee, S.D. Chambreau, A.G. Suits, Y. Zhang, J. Rheinecker, L.B. Harding, and J.M. Bowman Science 306 2004 1158
75. S.A. Lahankar, S.D. Chambreau, D. Townsend, F. Suits, J. Farnum, X. Zhang, J.M. Bowman, and A.G. Suits J. Chem. Phys. 125 2006 44303
76. J.M. Bowman, and X. Zhang Phys. Chem. Chem. Phys. 8 2006 321
77. A.G. Suits, S.D. Chambreau, and S.A. Lahankar Int. Rev. Phys. Chem. 26 2007 585
78. N. Herath, and A.G. Suits J. Phys. Chem. Lett. 2 2011 642
79. J.M. Bowman Proc. Natl. Acad. Sci. U.S.A. 103 2006 16061
80. B.C. Shepler, B.J. Braams, and J.M. Bowman J. Phys. Chem. A 111 2007 8282
81. B.R. Heazlewood, M.J.T. Jordan, S.H. Kable, T.M. Selby, D.L. Osborn, B.C. Shepler, B.J. Braams, and J.M. Bowman Proc. Natl. Acad. Sci. U.S.A. 105 2008 12719
82. P.L. Houston, and S.H. Kable PNAS 103 2006 16079
83. B.C. Shepler, B.J. Braams, and J.M. Bowman J. Phys. Chem. A 112 2008 9344
84. K.L.K. Lee, M.S. Quinn, A.T. Maccarone, K. Nauta, P.L. Houston, S.A. Reid, M.J.T. Jordan, and S.H. Kable Chem. Sci. 5 2014 4633
85. P.-Y. Tsai, K.-C. Hung, H.-K. Li, and K.-C. Lin J. Phys. Chem. Lett. 5 2014 190
86. S. Maeda, T. Taketsugu, and K. Morokuma J. Phys. Chem. Lett. 3 2012 1900
87. C. Chen, B.C. Shepler, and J.M. Bowman Phys. Chem. Chem. Phys. 11 2009 4722
88. R.S. Zhu, and M.C. Lin Chem. Phys. Lett. 478 2009 11
89. Z. Homayoon, and J.M. Bowman J. Phys. Chem. A 117 2013 11665
90. Z. Homayoon, J.M. Bowman, A. Dey, C. Abeysekera, R. Fernando, and A.G. Suits Phys. Chem. 227 2013 1267
91. E. Kamarchik, L. Koziol, H. Reisler, J.M. Bowman, and A.I. Krylov J. Phys. Chem. Lett. 1 2010 3058
92. R. Sivaramakrishnan, J.V. Michael, J.V. Wagner, J.V. Dawes, J.V. Jasper, J.V. Harding, J.V. Georgievskii, and S.J. Klippenstein Combust. Flame 158 2011 618
93. M.P. Grubb, M.L. Warter, A.G. Suits, and S.W. North J. Phys. Chem. Lett. 1 2010 2455
94. M.P. Grubb, M.L. Warter, H. Xiao, S. Maeda, K. Morokuma, and S.W. North Science 335 2012 1075
95. H. Xiao, S. Maeda, and K. Morokuma J. Chem. Theory Comput. 8 2012 2600
96. B. Fu, J.M. Bowman, H. Xiao, S. Maeda, and K. Morokuma J. Chem. Theory Comput. 9 2013 893
97. L.B. Harding, and S.J. Klippenstein J. Phys. Chem. Lett. 1 2010 3016
98. R. Sivaramakrishnan, M.-C. Su, J.V. Michael, S.J. Klippenstein, L.B. Harding, and B. Ruscic J. Phys. Chem. A 115 2011 3366
99. J.O. Thomas, K.E. Lower, and C. Murray J. Phys. Chem. Lett. 3 2012 1341
100. M.L. Hause, N. Herath, R. Zhu, M.C. Lin, and A.G. Suits Nat. Chem. 3 2011 932
101. B. Joalland, Y. Shi, A. Kamasah, A.G. Suits, and A.M. Mebel Nature 5 2014 4064
102. K.M. Christoffel, and J.M. Bowman J. Phys. Chem. A 113 2009 4138
103. Reprinted with permission from A.G. Suits Acc. Chem. Res. 41 2008 873
104. B.R. Heazlewood, M.J.T. Jordan, S.H. Kable, T.M. Selby, D.L. Osborn, B.C. Shepler, B.J. Braams, and J.M. Bowman PNAS 105 2008 12719
105. J.C. Owrutsky, D. Raftery, and R.M. Hochstrasser Annu. Rev. Phys. Chem. 45 1994 519
106. M.L. Cowan, B.D. Bruner, N. Huse, J.R. Dwyer, B. Chugh, E.T.J. Nibbering, T. Elsaesser, and R.J.D. Miller Nature 434 2005 199
107. M. Ji, M. Odelius, and K.J. Gaffney Science 328 2010 1003
108. J.D. Rynbrandt, and B.S. Rabinovitch J. Chem. Phys. 54 1971 2275
109. J.D. Rynbrandt, and B.S. Rabinovitch J. Chem. Phys. 75 1971 2164
110. P. Valtrazano, and K. Ruedenberg Theor. Chim. Acta 69 1986 281
111. P. Valtazanos, S.T. Elbert, S. Xantheas, and K. Ruedenberg Theor. Chim. Acta 78 1991 287
112. J. Baker, and P.M.W. Gill J. Comput. Chem. 9 1988 465
113. T. Taketsugu, and T. Hirano J. Chem. Phys. 99 1993 9806
114. Y. Harabuchi, and T. Taketsugu Theor. Chem. Acc. 130 2011 305
115. P. Collins, B.K. Carpenter, G.S. Ezra, and S. Wiggins J. Chem. Phys. 139 2013 154108
116. B.K. Carpenter Theor. Chem. Acc. 133 2014 1525
117. S. Maeda, Y. Harabuchi, Y. Ono, T. Taketsugu, and K. Morokuma Int. J. Quantum Chem. 115 2015 1097
118. F.A.L. Mauguiére, P. Collins, G.S. Ezra, S.C. Farantos, and S. Wiggins Chem. Phys. Lett. 592 2014 282
119. D.U. Andrews, S.H. Kable, and M.J.T. Jordan J. Phys. Chem. A 117 2013 7631
120. S.J. Klippenstein, Y. Georgievs kii, and L.B. Harding J. Phys. Chem. A 115 2011 14370