New applications of isotope effects in the determination of organic reaction mechanisms

Advances in Physical Organic Chemistry

Volumn 46, Issue , 2012, Pages 57-120

  Meyer, Matthew P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84868132395     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-398484-5.00002-X     Document Type: Chapter

References (249)

1. A. Kohen, and H.-H. Limbach Isotope Effects in Chemistry and Biology 2006 Taylor & Francis Boca Raton, FL
2. M. Wolfsberg, W.A. van Hook, and P. Paneth Isotope Effects in the Chemical, Geological, and Bio Sciences 2010 Springer New York
3. P. Muller Pure Appl Chem 66 1994 1077 1084
4. F.H. Westheimer Chem Rev 61 1961 265 273
5. H. Eyring J Chem Phys 3 1935 107 115
6. O. Redlich Z Phys Chem B 28 1935 371 382
7. J. Bigeleisen J Chem Phys 17 1949 675 678
8. J. Bigeleisen, and M. Wolfsberg Adv Chem Phys 1 1958 15 76
9. N. Fröman, and P.O. Fröman JWKB Approximation: Contributions to the Theory 1965 North-Holland Publishing Company Amsterdam
10. Many references include typographical errors in this equation. Northrop provides the typographically correct expression here: D.B. Northrop J Am Chem Soc 121 1999 3521 3524
11. R.P. Bell Trans Faraday Soc 55 1959 1 4
12. L. Melander, and W.H. Saunders Jr. Reaction Rates of Isotopic Molecules 1987 Robert E. Krieger Publishing Co. Malabar, FL 15
13. K. Toth, T.L. Amyes, B.M. Wood, K. Chan, J.A. Gerlt, and J.P. Richard J Am Chem Soc 132 2010 7018 7024
14. S.O.C. Mundle, G. Lacrampe-Couloume, B. Sherwood Lollar, and R.J. Kluger J Am Chem Soc 132 2010 2430 2436
15. J.S. Cannon, S.F. Kirsch, L.E. Overman, and H.F. Sneddon J Am Chem Soc 132 2010 15192 15203
16. S.Y. Seo, X. Yu, and T.J. Marks J Am Chem Soc 131 2009 263 276
17. S. Rousseaux, S.I. Gorelsky, B.K.W. Chung, and K. Fagnou J Am Chem Soc 132 2010 10692 10705
18. N.R. Deprez, and M.S. Sanford J Am Chem Soc 131 2009 11234 11241
19. H. Gaweska, M. Henderson Pozzi, D.M.Z. Schmidt, D.G. McCafferty, and P.F. Fitzpatrick Biochemistry 48 2009 5440 5445
20. 14 N KIE example: J.F. Marlier, E.J. Fogle, and W.W. Cleland Biochemistry 47 2008 11158 11163
21. 16 O KIE example: K.J. Humphreys, L.M. Mirica, Y. Wang, and J.P. Klinman J Am Chem Soc 131 2009 4657 4663
22. 12 C KIE example: P.A. Schwartz, M.J. Vetticatt, and V.L. Schramm Biochemistry 50 2011 1412 1420
23. 37 Cl KIE example: A. Lewandowicz, J. Rudziński, L. Tronstad, M. Widersten, P. Ryberg, O. Matsson, and P. Paneth J Am Chem Soc 123 2001 4550 4555
24. 37 Cl KIE example: K.C. Westaway, Y.R. Fang, S. MacMillar, O. Matsson, R.A. Poirier, and S.M. Islam J Phys Chem A 111 2007 8110 8120
25. R.P. Bell The Tunnel Effect in Chemistry 1980 Chapman and Hall London
26. M.J. Stern, and R.E. Weston Jr. J Chem Phys 60 1974 2808 2814
27. T. Giagou, and M.P. Meyer J Org Chem 75 2010 8088 8099
28. X. Creary, M. Keller, and J.P. Dinnocenzo J Org Chem 43 1978 3874 3878
29. H.U. Siehl, and H. Walter J Am Chem Soc 106 1984 5355 5356
30. M. Amin, R.C. Price, and W.H. Saunders Jr. J Am Chem Soc 112 1990 4467 4471
31. A. Streitweiser Jr., R.H. Jagow, R.C. Fahey, and S. Suzuki J Am Chem Soc 80 1958 2326 2332
32. I.H. Williams J Am Chem Soc 106 1984 7206 7212
33. X.G. Zhao, S.C. Tucker, and D.G. Truhlar J Am Chem Soc 113 1991 826 832
34. S. Wolfe, and C.K. Kim J Am Chem Soc 113 1991 8056 8061
35. E.A. Halevi Secondary Isotope Effects. Chap. 4 S.G. Cohen, A. Streitweiser Jr, R.W. Taft Jr., Progress in Physical Organic Chemistry Vol. 1 1963 Interscience New York
36. A. Streitweiser Jr., and H.S. Klein J Am Chem Soc 85 1963 2759 2763
37. T.A. Mitchell, and J.W. Bode J Am Chem Soc 131 2009 18057 18059
38. J.J. Gajewski, W. Bocian, N.J. Harris, L.P. Olson, and J.P. Gajewski J Am Chem Soc 121 1999 326 334
39. Y. Kim, A.V. Marenich, J. Zheng, K.H. Kim, M. Kołodziejska-Huben, and M. Rostkowski J Chem Theory Comput 5 2009 59 67
40. A. Streitwieser Jr, and P.M. Nair Tetrahedron 5 1959 149 165
41. E.S. Lewis Tetrahedron 5 1959 143 148
42. V.J. Shiner Jr. Tetrahedron 5 1959 243 247
43. K.L. Servis, S. Borčić, and D.E. Sunko Tetrahedron 24 1968 1247 1253
44. M. Meot-Ner J Am Chem Soc 109 1987 7947 7950
45. D.J. DeFrees, W.J. Hehre, and D.E. Sunko J Am Chem Soc 101 1979 2323 2327
46. V.J. Shiner Jr., and J.G. Jewett J Am Chem Soc 86 1964 945 946
47. D.E. Sunko, I. Szele, and W.J. Hehre J Am Chem Soc 99 1977 5000 5005
48. J.R. Tormos, K.L. Wiley, Y. Wang, D. Fournier, P. Masson, F. Nachon, and D.M. Quinn J Am Chem Soc 132 2010 17751 17759
49. P.A. Schwartz, M.J. Vetticatt, and V.L. Schramm Biochemistry 50 2011 1412 1420
50. I.H. Williams Chem Comm 1985 510 511
51. B.L. Murr, A. Nickon, T. Swarz, and H.N. Werstuik J Am Chem Soc 89 1967 1730 1732
52. E.C.F. Ko, and R.E. Robertson J Am Chem Soc 94 1972 573 575
53. L.S. Bartell Tetrahedron Lett 1960 13 16
54. L.S. Bartell Iowa State J Sci 36 1961 137 146
55. L.S. Bartell Tetrahedron 17 1961 177 190
56. L.S. Bartell J Am Chem Soc 83 1961 3567 3571
57. R.E. Carter, and L. Kahlgren Acta Chem Scand 23 1969 504 514
58. K. Mislow, R. Graeve, A.J. Gordon, and G.H. Wahl Jr. J Am Chem Soc 86 1964 1733 1741
59. K. Mislow, R. Graeve, A.J. Gordon, and G.H. Wahl Jr. J Am Chem Soc 85 1963 1199 1200
60. L. Melander, and R.E. Carter J Am Chem Soc 86 1964 295 296
61. S.A. Sherrod, R.L. da Costa, R.A. Barnes, and V. Boekelheide J Am Chem Soc 96 1974 1565 1577
62. P. Geneste, and G. Lamaty Tetrahedron Lett. 1965 4633 4638
63. L.R.C. Barclay, J.R. Mercer, and P.J. MacAulay Can J Chem 53 1975 3171 3174
64. R.W. Nagorski, H. Slebocka-Tilk, and R.S. Brown J Am Chem Soc 116 1994 419 420
65. R.C. Badger, and J.L. Fry J Am Chem Soc 101 1979 1680 1687
66. J.S. Mugridge, R.G. Bergman, and K.N. Raymond Angew Chem Int Ed 49 2010 3635 3637
67. T. Hayama, K.K. Baldridge, T.T. Wu, A. Linden, and J.S. Siegel J Am Chem Soc 130 2008 1583 1591
68. T. Felder, and C.A. Schalley Angew Chem Int Ed 42 2003 2258 2260
69. M. Saunders, M. Wolfsberg, F.A.L. Anet, and O. Kronja J Am Chem Soc 129 2007 10276 10281
70. F.A.L. Anet, V.J. Basus, A.P.W. Hewett, and M. Saunders J Am Chem Soc 102 1980 3945 3946
71. Zhu H; O'Leary DJ; Meyer MP. To be submitted.
72. Fong AYW; O'Leary DJ; Meyer MP. To be submitted.
73. G.S. Hammond J Am Chem Soc 77 1955 334 338
74. J.E. Leffler Science 117 1953 340 341
75. J.L. Hogg Secondary Hydrogen Isotope Effects R.D. Goundour, R.L. Schowen, Transition States of Biochemical Processes 1978 Plenum New York 201 224
76. V.J. Shiner Jr. Deuterium Isotope Effects in Solvolytic Substitution C.J. Collins, N.S. Bowman, Isotope Effects in Chemical Reactions 1970 Van Nostrand Reinhold New York 90 159
77. E.R. Pohl, and D.J. Hupe J Am Chem Soc 102 1980 2763 2768
78. L. do Amaral, M.P. Bastos, H.G. Bull, J.J. Ortiz, and E.H. Cordes J Am Chem Soc 101 1979 169 173
79. J.F. Kirsch Secondary Kinetic Isotope Effects W.W. Cleland, M.H. O'Leary, D.B. Northrop, Isotope Effects on Enzyme-Catalyzed Reactions 1977 University Park Press Baltimore, MD 100 121
80. I.M. Kovach, J.P. Elrod, and R.L. Schowen J Am Chem Soc 102 1980 7530 7534
81. J.J. Gajewski, and N.D. Conrad J Am Chem Soc 101 1979 6693 6704
82. J.J. Gajewski Acc Chem Res 13 1980 142 148
83. J.J. Gajewski, J. Jurayj, D.R. Kimbrough, M.E. Gande, B. Ganem, and B.K. Carpenter J Am Chem Soc 109 1987 1170 1186
84. D. Ostović, R.M.G. Roberts, and M.M. Kreevoy J Am Chem Soc 105 1983 7629 7631
85. R.A. Poirier, Y. Wang, and K.C. Westaway J Am Chem Soc 116 1994 2526 2533
86. Y. Kim, and M.M. Kreevoy J Am Chem Soc 114 1992 7116 7123
87. M. Amin, R.C. Price, and W.H. Saunders Jr. J Am Chem Soc 110 1988 4085 4086
88. W.P. Huskey, and R.L. Schowen J Am Chem Soc 105 1983 5704 5706
89. P.F. Cook, N.J. Oppenheimer, and W.W. Cleland Biochemistry 20 1981 1817 1825
90. K.M. Welsh, D.J. Creighton, and J.P. Klinman Biochemistry 19 1980 2005 2016
91. L.C. Kurz, and C. Frieden J Am Chem Soc 102 1980 4198 4203
92. J.D. Hermes, S.W. Morrical, M.H. O'Leary, and W.W. Cleland Biochemistry 23 1984 5479 5488
93. C.R. Pudney, S. Hay, M.J. Sutcliffe, and N.S. Scrutton J Am Chem Soc 128 2006 14053 14058
94. W.E. Karsten, C.C. Hwang, and P.F. Cook Biochemistry 38 1999 4398 4402
95. A. Streitwieser, R.H. Jagow, R.C. Fahey, and F. Suzuki J Am Chem Soc 80 1958 2326 2332
96. C.G. Swain, E.C. Stivers, J.F. Reuwer Jr., and L.J. Schaad J Am Chem Soc 80 1958 5885 5893
97. J. Hirschi, and D.A. Singleton J Am Chem Soc 127 2005 3294 3295
98. W.P. Huskey J Phys Org Chem 4 1991 361 366
99. M.I. Schimerlik, J.F. Rife, and W.W. Cleland Biochemistry 14 1975 5347 5354
100. J.P. Roth Acc Chem Res 42 2009 399 408
101. R.A. Pascal, M.W. Baum, C.K. Wagner, L.R. Rodgers, and D.-S. Huan J Am Chem Soc 108 1986 6477 6482
102. D.A. Singleton, and A.A. Thomas J Am Chem Soc 117 1995 9357 9358
103. N. Yoshikai, H. Matsuda, and E. Nakamura J Am Chem Soc 131 2009 9590 9599
104. J.K. Lee, A.D. Bain, and P.J. Berti J Am Chem Soc 126 2004 3769 3776
105. M.P. Meyer, and J.P. Klinman J Am Chem Soc 133 2011 430 439
106. J. Chan, A.R. Lewis, M. Gilbert, M.F. Karwaski, and A.J. Bennet Nat Chem Biol 6 2010 405 407
107. X. Guo, and M.L. Sinnott Biochem J 294 1993 653 656
108. D.J. Cram, and F.A.A. Elhafez J Am Chem Soc 74 1952 5828 5835
109. D.A. Evans, M.J. Dart, J.L. Duffy, and M.G. Yang J Am Chem Soc 118 1996 4322 4343
110. M.T. Reetz, K. Kesseler, and A. Jung Tetrahedron Lett 25 1984 729 735
111. T.J. Leitering, and D.J. Cram J Am Chem Soc 90 1968 4019 4026
112. T.J. Leitering, and D.J. Cram J Am Chem Soc. 90 1968 4011 4018
113. J.W. Cornforth, M.R.H. Cornforth, and K.K. Mathew J Chem Soc 1959 112 127
114. M. Chérest, H. Felkin, and N. Prudent Tetrahedron Lett 9 1968 2199 2204
115. H.E. Zimmerman, and M.D. Traxler J Am Chem Soc 79 1957 1920 1923
116. W.R. Roush J Org Chem 56 1991 4151 4157
117. P. Vittorelli, T. Winkler, H.-J. Hansen, and H. Schmid Helv Chim Acta 51 1968 1457 1461
118. D.A. Evans, E. Vogel, and J.V. Nelson J Am Chem Soc 101 1979 6120 6123
119. S. Winstein, and N.J. Holness J Am Chem Soc 77 1955 5562 5578
120. R.W. Taft J Am Chem Soc 74 1952 3120 3128
121. R.W. Taft J Am Chem Soc 74 1952 2729 2732
122. R.W. Taft J Am Chem Soc 75 1953 4538 4539
123. M. Charton J Am Chem Soc 91 1969 615 618
124. M. Charton J Am Chem Soc 97 1975 1552 1556
125. M. Charton J Org Chem 41 1976 2217 2220
126. J.H. Wu, G. Zhang, and N.A. Porter Tetrahedron Lett 38 1997 2067 2070
127. M.S. Sigman, and J.J. Miller J Org Chem 74 2009 7633 7643
128. J.J. Miller, and M.S. Sigman Angew Chem Int Ed 47 2008 771 774
129. J.L. Gustafson, M.S. Sigman, and S.J. Miller Org Lett 12 2010 2794 2797
130. L. Liao, and M.S. Sigman J Am Chem Soc 132 2010 10209 10211
131. H. Zhu, N.S. Reyes, and M.P. Meyer Tetrahedron Lett 50 2009 6803 6806
132. T.G. Giagou, and M.P. Meyer Chem Eur J 16 2010 10616 10628
133. J.D. West, S.E. Stafford, and M.P. Meyer J Am Chem Soc 130 2008 7816 7817
134. J.C. Decius, and E.B. Wilson Jr. J Chem Phys 19 1951 1409 1412
135. H.C. Brown, J. Chandrasekharan, and P.V. Ramachandran J Am Chem Soc 110 1988 1539 1546
136. E.J. Corey, and C.J. Helal Angew Chem Int Ed 37 1998 1986 2012
137. D. Liu, S. Hong, and E.J. Corey J Am Chem Soc 128 2006 8160 8161
138. G. Zhou, and E.J. Corey J Am Chem Soc 127 2005 11958 11959
139. E.J. Corey Angew Chem Int Ed. 41 2002 1650 1667
140. E.J. Corey Angew Chem Int Ed 48 2009 2100 2117
141. E.J. Corey, and J.O. Link Tetrahedron Lett 31 1990 601 604
142. D.K. Jones, D.C. Liotta, I. Shinkai, and D.J. Mathre J Org Chem 58 1993 799 801
143. X. Wang, J. Du, H. Liu, D.-M. Du, and J. Xu Heteroatom Chem 18 2007 740 746
144. E.J. Corey, R.K. Bakshi, and S. Shibata J Am Chem Soc 109 1987 5551 5553
145. E.J. Corey, and J.O. Link Tetrahedron Lett 33 1992 4141 4144
146. M.P. Meyer Org Lett 11 2009 4338 4341
147. G. Alagona, C. Ghio, M. Persico, and S. Tomasi J Am Chem Soc 125 2003 10027 10039
148. J. Saavedra, S.E. Stafford, and M.P. Meyer Tetrahedron Lett 50 2009 1324 1327
149. S.E. Stafford, and M.P. Meyer Tetrahedron Lett 50 2009 3027 3030
150. H. Zhu, F.R. Clemente, K.N. Houk, and M.P. Meyer J Am Chem Soc 131 2009 1632 1633
151. F.R. Clemente, and K.N. Houk Angew Chem Int Ed 43 2004 5766 5768
152. R.H. Newman-Evans, and B.K. Carpenter J Am Chem Soc 106 1984 7994 7995
153. B.K. Carpenter Acc Chem Res 25 1992 520 528
154. M.V. Basilevsky Chem Phys 24 1977 81 89
155. B. Grdina, M. Orfanopoulos, and L.M. Stephenson J Am Chem Soc 101 1979 3111 3112
156. K. Gollnick, H. Hartmann, and H. Paur On the Mechanism of the Ene-reactions with Singlet Oxygen O2(1Δg): Dependance of Rates on Solvent Polarity and Structure M.A.J. Rodgers, E.L. Powers, Oxygen and Oxy-Radicals in Chemistry and Biology 1981 Academic Press New York 379 395
157. D.A. Singleton, C. Hang, M.J. Szymanski, M.P. Meyer, A.G. Leach, and K.T. Kuwata J Am Chem Soc 125 2003 1319 1328
158. K.K. Kelly, J.S. Hirschi, and D.A. Singleton J Am Chem Soc 131 2009 8382 8383
159. P. Caramella, P. Quadrelli, and L. Toma J Am Chem Soc 124 2002 1130 1131
160. O.M. Gonzalez-James, E.E. Kwan, and D.A. Singleton J Am Chem Soc 134 2012 1914 1917
161. L. Xu, C.E. Doubleday, and K.N. Houk J Am Chem Soc 132 2010 3029 3037
162. A. Gonzalez-Lafont, M. Moreno, and J.M. Lluch J Am Chem Soc 126 2004 13089 13094
163. L. Pauling Nature 161 1948 707 709
164. R.L. Schowen Catalytic Power and Transition-State Stabilization R.D. Goundour, R.L. Schowen, Transition States of Biochemical Processes 1978 Plenum New York 77 114
165. Z.D. Nagel, and J.P. Klinman Nature Chem Bio 5 2009 543 550
166. E. Kuntz, A. Chen, K.A. Sharp, and P.A. Kollman Proc Natl Acad Sci U S A 96 1999 9997 10002
167. T.C. Bruice Acc Chem Res 35 2002 139 148
168. W.P. Jencks Adv Enzymol Relat Areas Mol Biol 43 1975 219 410
169. S.J. Benkovic, and S. Hammes-Schiffer Science 301 2003 1196 1202
170. A. Warshel J Biol Chem 273 1998 27035 27038
171. M. Garcia-Viloca, J. Gao, M. Karplus, and D.G. Truhlar Science 303 2004 186 195
172. X. Zhang, and K.N. Houk Acc Chem Res 38 2005 379 385
173. R. Wolfenden Annu Rev Biophys Bioeng 5 1975 271 306
174. A. Radzicka, and R. Wolfenden Methods. Enzymol. 249 1995 284 312
175. B.E. Lewis, and V.L. Schramm J Am Chem Soc 125 2003 4672 4673
176. R.D. LaReau, W. Wan, and V.E. Anderson Biochemistry 28 1989 3619 3624
177. B.E. Lewis, and V.L. Schramm J Am Chem Soc 125 2003 4785 4798
178. E. Gawlita, P. Paneth, and V.E. Anderson Biochemistry 34 1995 6050 6058
179. Y. Zhang, M. Luo, and V.L. Schramm J Am Chem Soc 131 2009 4685 4694
180. Y. Zhang, and V.L. Schramm Biochemistry 50 2011 4813 4818
181. S.J. Benkovic, and S. Hammes-Schiffer Science 301 2003 1196 1202
182. J.P. Klinman Nat Chem Biol 2 2010 907 909
183. V.L. Schramm Annu Rev Biochem 80 2011 703 722
184. Z.D. Nagel, and J.P. Klinman Chem Rev 106 2006 3095 3118
185. R.G. Silva, A.S. Murkin, and V.L. Schramm Proc Natl Acad Sci USA 108 2011 18661 18665
186. I.A. Rose Methods Enzymol 64 1980 47 59
187. L.J. Hyland, T.A. Tomaszek Jr., and T.D. Meek Biochemistry 30 1991 8454 8463
188. D.R. Kipp, R.G. Silva, and V.L. Schramm J Am Chem Soc 133 2011 19358 19361
189. M. Turowski, N. Yamakawa, J. Meller, K. Kimata, T. Ikegami, and K. Hosoya J Am Chem Soc 125 2003 13836 13849
190. G.P. Cartoni, and I. Ferreti J Chromatogr 122 1976 287 291
191. N. Tanaka, and E.R. Thornton J Am Chem Soc 99 1977 7300 7307
192. N. Tanaka, and E.R. Thornton J Am Chem Soc 98 1976 1617 1619
193. W.J.S. Lockley Chromatography 483 1989 413 418
194. P.R. Lewis, E. Johansen, and T.R. Holman J Am Chem Soc 121 1999 1395 1396
195. M.A. Spies, and M.D. Toney J Am Chem Soc 129 2007 10678 10685
196. B.J. Bahnson, and V.E. Anderson Biochemistry 30 1991 5894 5906
197. M.I. Schimerlik, J.E. Rife, and W.W. Cleland Biochemistry 14 1975 5347 5354
198. J.D. Dunitz, and R.M. Ibberson Angew Chem Int Ed 47 2008 4208 4210
199. R. Gelabert, M. Moreno, and J.M. Lluch J Phys Chem A 113 2009 14161 14169
200. K. Mislow, E. Simon, and H.B. Hopps Tetrahedron Lett 1962 1011 1014
201. L.S. Bartell Tetrahedron Lett 6 1960 13 17
202. L.S. Bartell J Am Chem Soc 83 1961 3567 3571
203. D.J. O'Leary, P.R. Rablen, and M.P. Meyer Angew Chem Int Ed 50 2011 2564 2567
204. Y. Wu, R.P. Singh, and L. Deng J Am Chem Soc 133 2011 12458 12461
205. D.H. Lee, K.H. Kwon, and C.S. Yi Science 333 2011 1613 1616
206. D.E. Frantz, D.A. Singleton, and J.P. Snyder J Am Chem Soc 119 1997 3383 3384
207. D.-H. Lee, K.-H. Kwon, and C.S. Yi J Am Chem Soc 134 2012 7325 7328
208. J. Švenda, and A.G. Myers Org Lett 11 2009 2437 2440
209. J.L. Moore, A.P. Silvestri, J.R. de Alaniz, D.A. DiRocco, and T. Rovis Org Lett 13 2011 1742 1745
210. C.M. Rathbun, and J.B. Johnson J Am Chem Soc 133 2011 2031 2033
211. S.J. Ryan, A. Stasch, M.N. Paddon-Row, and D.W. Lupton J Org Chem 77 2011 1113 1124
212. K.J. Bartelson, R.P. Singh, B.M. Foxman, and L. Deng Chem Sci 2 2011 1940 1944
213. Z.D. Nagel, and J.P. Klinman Chem Rev 106 2006 3095 3118
214. Z.D. Nagel, and J.P. Klinman Nat Chem Biol 5 2009 543 550
215. A. Kohen Probes for Hydrogen Tunneling and Coupled Motion in Enzymatic Systems J.T. Hynes, J.P. Klinman, H.H. Limbach, R.L. Schowen, Hydrogen Transfer Reactions Vol. 4 2006 Wiley Weinheim, Germany 1311 1340
216. S. Hay, J. Pang, P.J. Monaghan, X. Wang, R.M. Evans, and M.J. Sutcliffe Chem Phys Chem 9 2008 1536 1539
217. J.P. Klinman Chem Phys Lett 471 2009 179 193
218. S. Hammes-Schiffer Acc Chem Res 39 2006 93 100
219. J.P. Klinman Philos Trans R Soc Lond B Biol Sci 361 2006 1323 1331
220. D.B. Northrop Philos Trans R Soc Lond B Biol Sci 361 2006 1341 1349
221. A. Kohen, and J.P. Klinman Chem Biol 6 1999 R191 R198
222. T. Jonsson, M.H. Glickman, S. Sun, and J.P. Klinman J Am Chem Soc 118 1996 10319 10320
223. K.W. Rickert, and J.P. Klinman Biochemistry 38 1999 12218 12228
224. M.P. Meyer, and J.P. Klinman J Am Chem Soc 133 2011 430 439
225. A.M. Kuznetsov, and J. Ulstrup Can J Chem 77 1999 1085 1096
226. M.J. Knapp, K. Rickert, and J.P. Klinman J Am Chem Soc 124 2002 3865 3874
227. E. Buhks, M. Bixon, and J. Jortner J Phys Chem 85 1981 3763 3766
228. K.-Y. Wong, J.P. Richard, and J. Gao J Am Chem Soc 131 2009 13963 13971
229. H. Kleinert Path Integrals in Quantum Mechanics, Statistics, Polymer Physics, and Financial Markets 3rd ed. 2004 World Scientific River Edge, NJ
230. H. Kleinert Phys Lett A 173 1993 332 342
231. J. Tomasi, B. Mennucci, and R. Cammi Chem Rev 105 2005 2999 3094
232. D.M. York, and M. Karplus J Phys Chem A 103 1999 11060 11079
233. R. Car, and M. Parrinello Phys Rev Lett 55 1985 2471 2474
234. A. Jezierska, J.J. Panek, A. Koll, and J. Mavri J Chem Phys 126 2007 205101
235. S. Lou, P.N. Moquist, and S.E. Schaus J Am Chem Soc 128 2006 12660 12661
236. H.M.L. Davies, and Q. Jin Proc Natl Acad Sci U S A 101 2004 5472 5475
237. B.H. Lipshutz, and S. Ghorai Aldrichim Acta 45 2012 3 16
238. U.H. Dolling, P. Davis, and E.J.J. Grabowski J Am Chem Soc 106 1984 446 447
239. S. Hong, J. Lee, M. Kim, Y. Park, C. Park, and M. Kim J Am Chem Soc 133 2011 4924 4929
240. D. Zuccaccia, L. Belpassi, F. Tarantelli, and A. Macchioni J Am Chem Soc 131 2009 3170 3171
241. R.L. LaLonde, Z.J. Wang, M. Mba, A.D. Lackner, and F.D. Toste Angew Chem Int Ed 49 2010 598 601
242. K.-H. Kwon, D.W. Lee, and C.S. Yi Organometallics 29 2010 5748 5750
243. S.E. Bromberg, H. Yang, M.C. Asplund, T. Lian, B.K. McNamara, and K.T. Kotz Science 278 1997 260 263
244. A.D. Ryabov Chem Rev. 90 1990 403 424
245. G. Parkin Acc Chem Res 42 2009 315 325
246. D.G. Blackmond Angew Chem Int Ed 44 2005 4302 4320
247. J.S. Mathew, M. Klussmann, H. Iwamura, F. Valera, A. Futran, and E.A.C. Emanuelsson J Org Chem 71 2006 4711 4722
248. K.C. Harper, and M.S. Sigman Proc Natl Acad Sci U S A 108 2011 2179 2183
249. K.C. Harper, and M.S. Sigman Science 333 2011 1875 1878