Rehybridization as a general mechanism for maximizing chemical and supramolecular bonding and a driving force for chemical reactions

Journal of Computational Chemistry

Volumn 28, Issue 1, 2007, Pages 373-390

  Alabugin, Igor V ^a   Manoharan, Mariappan ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Cycloaromatization; Hybridization; Hydrogen bonding; Rehybridization; s character; Stereoelectronic effects; Strain

Indexed keywords

CYCLOAROMATIZATION; REHYBRIDIZATION; S-CHARACTER; STEREOELECTRONIC EFFECTS;

AROMATIZATION; COMPLEXATION; COMPUTATION THEORY; HYDROGEN BONDS; MOLECULAR DYNAMICS; REACTION KINETICS; STRAIN;

CHEMICAL BONDS;

EID: 33846606944     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.20524     Document Type: Article

References (195)

1. (a) Pauling, L. J Am Chem Soc 1931, 58, 1367;
2. (b) Pauling, L. Proc Natl Acad Sci USA 1976, 73, 274.
3. (a) Lewis, G. N. J Am Chem Soc 1916, 38, 762;
4. (b) Lewis, G. N. Valence and Structure of Atoms and Molecules; Chemical Catalog: New York, 1923.
5. (a) Foster, J. P.; Weinhold, F. J Am Chem Soc 1980, 102, 7211;
6. (b) Huheey, J. E. Inorg Chem 1981, 20, 4033;
7. (c) Kaupp, M.; Schleyer, P. v. R. J Am Chem Soc 1993, 115, 1061;
8. (d) Root, D. M.; Landis, C. R.; Cleveland, T. J Am Chem Soc 1993, 115, 4201;
9. (e) Jonas, V.; Boehme, C.; Frenking, G. Inorg Chem 1996, 35, 2097;
10. (f) Kaupp, M. Chem Eur J 1999, 5, 3631;
11. (g) Lemke, F. R.; Galat, K. J.; Youngs, W. J. Organometallics 1999, 18, 1419;
12. (h) Kaupp, M. Angew Chem Int Ed Engl 2001, 40, 3534;
13. (i) Ferbinteanu, M.; Roesky, H. W.; Cimpoesu, F.; Atanasov, M.; Kopke, S.; Herbst-Irmer, R. Inorg Chem 2001, 40, 4947;
14. (j) Ghosh, D. C.; Bhattacharyya, S. Int J Quantum Chem 2005, 105, 270;
15. (k) Alabugin, I. V.; Manoharan, M. (in preparation).
16. (a) Kutzelnigg, W. Angew Chem Int Ed Engl 1984, 96, 262;
17. (b) Kutzelnigg, W. Angew Chem Int Ed Engl 1984, 23, 272;
18. (c) Kutzelnigg, W. J Mol Struct (THEOCHEM) 1998, 169, 403.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian: Wallingford, CT, 2004.
20. (a) Becke, A. D. Phys Rev A 1988, 38, 3098;
21. (b) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys Rev B 1988, 37, 785.
22. Hobza, P.; Havlas, Z. Chem Rev 2000, 100, 4253.
23. (a) Hoffner, J.; Schottelius, M. J.; Feichtinger, D.; Chen, P. J. Am. Chem. Soc. 1998, 120, 376;
24. (b) Schottelius, M. J.; Chen, P. J Am Chem Soc 1996, 118, 4896;
25. (c) Logan, C. F.; Chen, P. J Am Chem Soc 1996, 118, 2113.
26. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev 1988, 88, 899;
27. (b) Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.0, Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 1996.
28. (a) Reed, A.E.; Weinhold, F. Isr J Chem 1991, 31, 277;
29. (b) Weinhold, F. J Mol Struct (THEOCHEM) 1997, 398, 181;
30. (c) Goodman, L.; Pophristic, V.; Weinhold, F. Acc Chem Res 1999, 32, 983;
31. (d) Goodman, L.; Pophristic, V. T. Nature 2001, 411, 565;
32. (e) Salzner, U.; Schleyer, P. v. R. J Org Chem 1994, 59, 2138;
33. (f) Gleiter, R.; Lange, H.; Borzyk, O. J Am Chem Soc 1996, 118, 4889;
34. (g) Freeman, F.; Lee, K.; Hehre, W. J Struct Chem 2002, 13, 149;
35. (h) Klod, S.; Koch, A.; Kleinpeter, E. J Chem Soc Perkin Trans II 2002, 1506;
36. (i) Alabugin, I. V.; Zeidan, T. A. J Am Chem Soc 2002, 124, 3175;
37. (j) Wilkens, S. J.; Westler, W. M.; Weinhold, F.; Markley, J. L. J Am Chem Soc 2002, 124, 1190;
38. (k) van der Veken, B. J.; Herrebout, W. A.; Szostak, R.; Shchepkin, D. N.; Havlas, Z.; Hobza, P. J Am Chem Soc 2001, 123, 12290;
39. (l) Lewis, B. E.; Schramm, V. L. J Am Chem Soc 2001, 123, 1327;
40. (m) Cortes, F.; Tenorio, J.; Collera, O.; Cuevas, G. J Org Chem 2001, 66, 2918;
41. (n) Sadlej-Sosnowska, N. J Org Chem 2001, 66, 8737;
42. (o) Uddin, J.; Boehme, C.; Frenking, G. Organometallics 2000, 19, 571;
43. (p) Alabugin, I. V. J Org Chem 2000, 65, 3910;
44. (q) Xie, Y.; Grev, R. S.; Gu, J.; Schaefer, H. F., III; Schleyer, P. v. R.; Su, J.; Li, X.-W.; Robinson, G. H. J Am Chem Soc 1998, 120, 3773;
45. (r) Paddon-Row, M. N.; Shephard, M. J. J Am Chem Soc 1997, 119, 5355.
46. (a) Edmiston, C.; Ruedenberg, K. Rev Mod Phys 1963, 34, 457;
47. (b) Edmiston, C.; Ruedenberg, K. J Chem Phys 1965, 43, S097;
48. (c) Foster, J. M.; Boys, S. F. Rev Mod Phys 1960, 32, 300;
49. (d) Boys, S. F. In Quantum Theory of Atoms, Molecules, and Solid State; Lowdin, P.-O., Ed.; Academic: New York, 1966; p. 253;
50. (e) Gordon, M. S.; Tallman, D. E.; Monroe, C.; Steinbach, M.; Armbrust, J. J Am Chem Soc 1975, 97, 1326;
51. (f) Morris, M. L.; Tallman, D. E.; Gordon, M. S. J Mol Struct 1976, 34, 263;
52. (g) Gordon, M. S.; Tallman, D. E. Chem Phys Lett 1972, 17, 385;
53. (h) Guest, M. F.; Hiller, I. Int J Quantum Chem 1972, 6, 967;
54. (i) Guest, M. F.; Hiller, I. H.; Saunders, V. R. J Chem Soc Fraday Trans II 1972, 68, 867;
55. (j) Pipek, J.; Mezey, P. G. J Chem Phys 1989, 90, 4916;
56. (k) Weinstein, H.; Pauncz, R. Symp Faraday Soc 1968, 2, 23;
57. (l) Magnasco, V.; Perico, A. J Chem Phys 1967, 47, 971;
58. (m) Kutzelnigg, W. Isr J Chem 1980, 19, 193;
59. (n) Kohn, W. Phys Rev B 1973, 7, 4388;
60. (o) Fornili, A.; Moreau, Y.; Sironi, M.; Assfeld, X. J Comp Chem 2006, 27, 515;
61. (p) Bhattacharjee, J.; Waghmare, U. V. Phys Rev B 2006, 73, 121102.
62. (a) Bent, H. A. J Chem Phys 1959, 33, 1258;
63. (b) Bent, H. A. J Chem Educ 1960, 37, 616;
64. (c) Bent, H. A. Chem Rev 1961, 61, 275.
65. (a) Baldridge, K. K.; Siegel, J. S. Chem Rev 2002, 124, 5514;
66. (b) Lemke, F. R.; Galat, K. J.; Youngs, W. J. Organometallics 1999, 18, 1419;
67. (c) Kaupp, M.; Malkina, O. L. J Chem Phys 1999, 108, 3648;
68. (d) Palmer, M. H. J Mol Struct 1997, 405, 179;
69. (e) Palmer, M. H. J Mol Struct 1997, 405, 193.
70. Sorger, K.; Schleyer, P. v. R.; Stalke, D. J Am Chem Soc 1996, 118, 1086.
71. Borden, W. T. Chem Rev 1989, 89, 1095.
72. Weinhold, F.; Landis, C. R.Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, UK, 2005; pp. 219-220.
73. Hamon, M. A.; Itkis, M. E.; Niyogi, S.; Alvaraez, T.; Kuper, C.; Menon, M.; Haddon, R. C. J Am Chem Soc 2001, 123, 11292.
74. Oxgaard, J.; Wiest, O. J Phys Chem A 2002, 106, 3967; Other interesting and thoroughly analyzed examples include:
75. (b) allyl cation, radical and anion: Mo, Y.; Lin, Z.; Wu, W.; Zhang, Q. J Phys Chem 1996, 100, 6469;
76. (c) carbenes and vinylidenes: Worthington, S. E.; Cramer, C. E. J Phys Org Chem 1997, 10, 755;
77. (d) p-benzynes: Clark, A. E.; Davidson, E. R. J Org Chem 2003, 68, 3387.
78. (a) Middleton, W. J. J Am Chem Soc 1959, 81, 803;
79. (b) Tyler, J. K.; Sheridan, J. Proc Chem Soc (London) 1960, 119;
80. (c) Morea, U. C.; Serre, J. Theor Chim Acta 1964, 2, 40;
81. (d) Weiss, V. W.; Todd, H. D.; Lo, M. K.; Gutowsky, H. S.; Flygare, W. H. J Chem Phys 1967, 47, 4021;
82. (e) Ditchfie, R.; Ellis, P. D. Chem Phys Lett 1972, 17, 342;
83. (f) Sauvetre, R.; Normant, J. F. Tetrahedron Lett 1982, 23, 4325;
84. (g) Botschwina, P.; Oswald, M.; Flugge, J.; Heyl, A.; Oswald, R. Chem Phys Lett 1993, 209, 117;
85. (h) Iachello, F.; Oss, S.; Viola, L. Mol Phys 1993, 78, 545;
86. (i) DeLeeuw, B. J.; Fermann, J. T.; Xie, Y.; Schaefer, H. F., III. J Am Chem Soc 1993, 115, 1039;
87. (j) Persson, B. J.; Taylor, P. R.; Martin, J. M. L. J Phys Chem A 1998, 102, 2483;
88. (k) Jayakumar, N.; Kolandaivel, P.; Kuze, N.; Sakasumi, T.; Ohashi, O. J Mol Struct (THEOCHEM) 1999, 465, 197;
89. (l) Middleton, W. J. J Fluor Chem 1999, 100, 207;
90. (m) Huckauf, A.; Guarnieri, A. J Mol Struct 2002, 213, 79;
91. (n) Medved, M.; Noga, J.; Jacquemin, D.; Perpete, E. A. Int J Quantum Chem 2005, 102, 209.
92. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983;
93. (b) Thatcher, G. R. J., Ed. The Anomeric Effect and Associated Stereoelectronic Effects; American Chemical Society: Washington, DC, 1993. ACS Symposium Series 539;
94. (c) Juaristi, E.; Guevas, G. The Anomeric Effect; CRC: Boca Raton, FL, 1994;
95. (d) Juaristi, E., Ed. Conformational Behavior of Six-Membered Rings; VCH: New York, 1995;
96. (e) Uehara, F.; Sato, M.; Kaneko, C.; Kurihara, H. J Org Chem 1999, 64, 1436.
97. (a) Anet, F. A. L.; Kopelevich, M. J Am Chem Soc 1986, 108, 2109;
98. (b) Anet, F. A. L.; Kopelevich, M. J Chem Soc Chem Commun 1987, 595;
99. (c) Salzner, U.; Schleyer P. v. R. J Org Chem 1994, 59, 2138;
100. (d) Juaristi, E.; Cuevas, G.; Vela, A. J Am Chem Soc 1994, 116, 5796;
101. (e) Juaristi, E.; Rosquete-Pina, G. A.; Vazquez-Hernandez, M.; Mota, A. J Pure Appl Chem 2003, 75, 589;
102. (f) Freeman, F.; Le, K. T. J Phys Chem A 2003, 107, 2908;
103. (g) Freeman, F.; Do' Katie U. J Mol Struct (THEOCHEM) 2002, 577, 43;
104. (h) Anderson, J. E.; Bloodworth, A. J.; Cai, J. Q.; Davies, A. G.; Schiesser, C. H. J Chem Soc Perkin Trans2 1993, 601;
105. (i) Cai, J. Q.; Davies, A. G.; Schiesser, C. H. J Chem Soc Perkin Trans2 1994, 1151;
106. (j) Juaristi, E.; Cuevas, G. Tetrahedron Lett 1992, 33, 1847;
107. (k) Juaristi, E.; Cuevas, G.; Flores-Vela, A. Tetrahedron Lett 1992, 33, 6927;
108. (l) Bailey, W. F.; Rivera, A. D.; Rossi, K. Tetrahedron Lett 1988, 29, 5621.
109. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983;
110. (b) Thatcher, G. R. J., Ed. The Anomeric Effect and Associated Stereoelectronic Effects; American Chemical Society: Washington, DC, 1993. ACS Symposium Series 539.
111. Nillson, A.; Ogasawara, H.; Cavalleri, M.; Nordlund, D.; Nyberg, M.; Wernet, Ph.; Pettersson, L. G. M. J Chem Phys 2005, 122, 154505.
112. (a) Alabugin, I. V.; Manoharan, M. J Am Chem Soc 2003, 125, 14014 and references cited therein;
113. (b) See also: Alabugin, I. V. J Org Chem 2000, 65, 3910;
114. (c) Alabugin, I. V.; Zeidan, T. A. J Am Chem Soc 2002, 124, 3175;
115. (d) Alabugin, I. V.; Manoharan, M. J Org Chem 2004, 69, 9011.
116. Cuevas, G.; Martínez-Mayorga, K.; Fernández-Alonso, M. d. C.; Jiménez-Barbero, J.; Perrin, C.; Juaristi, E.; López-Mora, N. Angew Chem Int Ed Engl 2005, 44, 2360.
117. Mills, W. H.; Nixon, I. G. J Chem Soc 1930, 2510.
118. (a) Diercks, R.; Vollhardt, K. P. C. J Am Chem Soc 1986, 108, 3150;
119. (b) Baldridge, K. K.; Siegel, J. S. J Am Chem Soc 1992, 114, 9583;
120. (c) Boese, R.; Bläser, D.; Billups, W. E.; Haley, M.; Maulitz, A.; Mohler, D. L.; Vollhardt, K. P. C. Angew Chem Int Ed Engl 1994, 33, 313;
121. (d) Bürgi, H.-B.; Baldridge, K. K.; Hardcastle, K.; Frank, N. L.; Gantzel, P.; Siegel, J. S.; Ziller, J. Angew Chem Int Ed Engl 1995, 34, 1454.
122. (a) Ou, M.-C.; Chu, S.-Y. J Mol Struct (THEOCHEM) 1997, 401, 87;
123. (b) Faust, R.; Glendening, E. D.; Streitwieser, A.; Vollhardt, K. P. C. J Am Chem Soc 1992, 114, 8263.
124. (a) Baldridge, K. K.; Siegel, J. S. J Am Chem Soc 1992, 114, 9583;
125. (b) Maksíc, Z. B.; Eckert- Maksíc, M.; Pfeifer, K.-H. J Mol Struct 1993, 300, 445;
126. (c) Ýaínes, O. M. O.; Eckert-Maksíc, M.; Maksíc, Z. B. J Org Chem 1995, 60, 1638;
127. (d) Eckert-Maksíc, M.; Glasovac, Z.; Maksíc, Z. B.; Zrinski, I. J Mol Struct (THEOCHEM) 1996, 366, 173;
128. (e) Stanger, A. J Am Chem Soc 1998, 120, 12034;
129. (f) Jemmis, E. D.; Kiran, B. J Org Chem 1996, 61, 9006;
130. (g) Shaik, S. S.; Hiberty, P. C.; Lefour, J.-M.; Ohanessian, G. J Am Chem Soc 1987, 109, 363;
131. (h) Shaik, S. S.; Hiberty, P. C. J Am Chem Soc 1985, 107, 3089;
132. (i) Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. Chem Rev 2001, 101, 1501;
133. (j) Baldridge, K. K.; Siegel, J. S. J Am Chem Soc 2002, 124, 5514.
134. Streitwieser, A.; Ziegler, G. R.; Mowery, P. C.; Lewis, A.; Lawler, R. G. J Am Chem Soc 1968, 90, 1357.
135. (a) Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J Am Chem Soc 2003, 125, 5973; See also:
136. (b) Mŕazkov́a, E.; Hobza, P. J Phys Chem A 2003, 107, 1032;
137. (c) Chocholouîsov́a, J.; Špirko, V.; Hobza, P. Phys Chem Chem Phys 2004, 6, 37;
138. (d) Vijayakumar, S.; Kolandaivel, P. J Mol Struct (THEOCHEM) 2005, 734, 157;
139. (e) Nilsson, A.; Ogasawara, H.; Cavalleri, M.; Nordlund, D.; Nyberg, M.; Pettersson, L. G. M. J Chem Phys 2005, 122, 154505;
140. (f) Wysokiînski, W.; Bieînko, D. C.; Michalska, D.; Zeegers-Huyskens, T. Chem Phys 2005, 315, 17.
141. (a) Li, X.; Liu, L.; Schlegel, H. B. J Am Chem Soc 2002, 124, 9639;
142. (b) McDowell, S. A. C.; Buckingham, A. D. J Am Chem Soc 2005, 127, 15515.
143. Scheiner, S.; Grabowski, S. J.; Kar, T. J Phys Chem A 2001, 105, 10607.
144. Wetmore, S. D.; Schofield, R.; Smith, D. M.; Radom, L. J Phys Chem A 2001, 105, 4470.
145. Hobza, P.; Havlas, Z. Chem Rev 2000, 100, 4253.
146. Masunov, A.; Dannenberg, J. J.; Contreras, R. H. J Phys Chem A 2001, 105, 4737.
147. Wang, J.-T.; Feng, Y.; Liu, L.; Li, X.-S.; Guo, Q.-X. Chem Lett 2003, 32, 746.
148. (a) McDowell, S. A. Phys Chem Chem Phys 2003, 5, 808 and related papers;
149. (b) Lignell, A.; Khriachtchev, L.; Pettersson, M.; Räsänen, M. J Chem Phys 2002, 117, 961;
150. (c) Alabugin, I. V.; Manoharan, M.; Weinhold, F. A. J Phys Chem A 2004, 108, 4720.
151. (a) Jones, R. R.; Bergman, R. G. J Am Chem Soc 1972, 94, 660;
152. (b) Bergman, R. G. Acc Chem Res 1973, 6, 25.
153. (a) Nicolaou, K. C.; Smith, A. L. Acc Chem Res 1992, 25, 497;
154. (b) Maier, M. E.; Bosse, F.; Niestroj, A. J. Eur J Org Chem 1999, 1, 1;
155. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 19, 6453;
156. (d) Fallis, A. G. Can J Chem 1999, 7, 159;
157. (e) Caddick, S.; Delisser, V. M.; Doyle, V. E.; Khan, S.; Avent, A. G.; Vile, S. Tetrahedron 1999, 55, 2737;
158. (f) Wang, K. K. Chem Rev 1996, 96, 207;
159. (g) Borders, D. B.; Doyle, T. W., Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995.
160. (a) Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, Germany, 2000; pp. 11-14;
161. (b) Black, K. A.; Wilsey, S.; Houk, K. N. J Am Chem Soc 1998, 120, 5622;
162. (c) Navarro-Vazquez, A.; Prall, M.; Schreiner, P. R. Org Lett 2004, 6, 2981.
163. (a) Koga, N.; Morokuma, K. J Am Chem Soc 1991, 113, 1907;
164. (b) Snyder, J. P. J Am Chem Soc 1990, 112, 5367;
165. (c) Magnus, P.; Carter, P.; Elliott, J.; Lewis, R.; Harling, J.; Pitterna, T.; Bauta, W. E.; Font, S. J Am Chem Soc 1992, 114, 2544;
166. (d) Kraka, E.; Cremer, D. J Am Chem Soc 1994, 116, 4929;
167. (e) Jones, G. B.; Plourde, G. W. Org Lett 2000, 2, 1757;
168. (f) Jones, G. B.; Warner, P. M. J Am Chem Soc 2001, 123, 2134;
169. (g) Plourde, G. W., II; Warner, P. M.; Parrish, D. A.; Jones, G. B. J Org Chem 2002, 67, 5369;
170. (h) Jones, G. B.; Wright, J. M.; Hynd, G.; Wyatt, J. K.; Warner, P. M.; Huber, R. S.; Li, A.; Kilgore, M. W.; Sticca, R. P.; Pollenz, R. S. J Org Chem 2002, 67, 5727;
171. (i) Haberhauer, G.; Gleiter, R. J Am Chem Soc 1999, 121, 4664;
172. (j) Koseki, S.; Fujimura, Y.; Hirama, M. J Phys Chem 1999, 103, 7672;
173. (k) Prall, M.; Wittkopp, A.; Schreiner, P. R. J Phys Chem A 2001, 105, 9265;
174. (l) Schreiner, P. R.; Prall, M. J Am Chem Soc 1999, 121, 8615;
175. (m) Schreiner, P. R. J Am Chem Soc 1998, 120, 4184.
176. (a) Galbraith, J. M.; Schreiner, P. R.; Harris, N.; Wei, W.; Wittkopp, A.; Shaik, S. Chem Eur J 2000, 6, 1446;
177. (b) Stahl, F.; Moran, D.; Schleyer, P. v. R.; Prall, M.; Schreiner, P. R. J Org Chem 2002, 67, 1453;
178. (c) Alabugin, I. V.; Manoharan, M. J Phys Chem A 2003, 107, 3363.
179. (a) Alabugin, I. V.; Kovalenko, S. J Am Chem Soc 2002, 124, 9052;
180. (b) Alabugin, I. V.; Manoharan, M. J Am Chem Soc 2003, 125, 4495.
181. (a) Alabugin, I. V.; Manoharan, M.; Kovalenko, S. V. Org Lett 2002, 4, 1119;
182. (b) Zeidan, T. A.; Manoharan, M.; Alabugin, I. V. J Org Chem 2006, 71, 954;
183. Zeidan, T. A.; Kovalenko, S. V.; Manoharan, M.; Alabugin, I. V. J Org Chem 2006, 71, 962;
184. (c) Pickard, F. C., IV; Shepherd, R. L.; Gillis, A. E.; Dunn, M. E.; Feldgus, S.; Kirschner, K. N.; Shields, G. C.; Manoharan, M.; Alabugin, I. V. J Phys Chem A 2006, 110, 2517;
185. (d) Choy, N.; Kim, C.-S.; Ballestero, C.; Argitas, L.; Diez, C.; Lichtenberg, F.; Shapiro, J.; Russell, K. C. Tetrahedron Lett 2000, 41, 6995;
186. (e) Boger, D. L.; Zhou, J. J Org Chem 1993, 58, 3018;
187. (f) Grissom, J. W.; Calkins, T. L.; McMillen, H. A.; Jiang, Y. J Org Chem 1994, 59, 5833.
188. Prall, M.; Wittkopp, A.; Fokin, A. A.; Schreiner, P. R. J Comp Chem 2001, 22, 1605.
189. Wenk, H. H.; Balster, A.; Sander, W.; Hrovat, D. A.; Borden, W. T. Angew Chem Int Ed Engl 2001, 40, 2295.
190. Jones, G. B.; Warner, P. M. J Am Chem Soc 2001, 66, 2134.
191. (a) Jones, G. B.; Plourde, G. W., II. Org Lett 2000, 2, 1757;
192. (b) Plourde, G. W., II; Warner, P. M.; Parrish, D. A.; Jones, G. B. J Org Chem 2002, 67, 5369.
193. (a) Lewis, M.; Glaser, R. J Am Chem Soc 1998, 120, 8541;
194. (b) Pu, J.; Ma, S.; Garcia-Viloca, M.; Gao, J.; Truhlar, D. G.; Kohen, A. J Am Chem Soc 2005, 127, 14879.
195. Lauvergnat, D.; Maitre, P.; Hiberty, P. C.; Volatron, F. J Phys Chem 1996, 100, 6463.