Role of Orbital Interactions and Activation Strain (Distortion Energies) on Reactivities in the Normal and Inverse Electron-Demand Cycloadditions of Strained and Unstrained Cycloalkenes

Journal of Organic Chemistry

Volumn 82, Issue 16, 2017, Pages 8668-8675

  Levandowski, Brian J ^a   Hamlin, Trevor A ^b   Bickelhaupt, F Matthias ^b,c   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; CHEMICAL REACTIONS; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; OLEFINS;

DIELS-ALDER REACTION; ENERGY DIFFERENCES; INTERACTION ENERGIES; INVERSE-ELECTRON DEMAND DIELS-ALDER REACTIONS; ORBITAL INTERACTION; REACTION COORDINATES; REACTIVITY TRENDS; TRANSITION STRUCTURES;

ACTIVATION ENERGY;

EID: 85027580860     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.7b01673     Document Type: Article

References (44)

1. Patterson, D. M.; Nazarova, L. A.; Xie, B.; Kamber, D. N.; Prescher, J. A. J. Am. Chem. Soc. 2012, 134, 18638 10.1021/ja3060436
2. Thalhammer, F.; Wallfahrer, U.; Sauer, J. Tetrahedron Lett. 1990, 31, 6851 10.1016/S0040-4039(00)97188-0
3. Liu, F.; Paton, R. S.; Kim, S.; Liang, Y.; Houk, K. N. J. Am. Chem. Soc. 2013, 135, 15642 10.1021/ja408437u
4. Bickelhaupt, F. M.; Houk, K. N. Angew. Chem., Int. Ed. 2017, 56, 2 10.1002/anie.201707253
5. Wolters, L. P.; Bickelhaupt, F. M. WIRES Comput. Mol. Sci. 2015, 5, 324 10.1002/wcms.1221
6. Fernández, I.; Bickelhaupt, F. M. Chem. Soc. Rev. 2014, 43, 4953 10.1039/C4CS00055B
7. van Zeist, W.-J.; Bickelhaupt, F. M. Org. Biomol. Chem. 2010, 8, 3118 10.1039/b926828f
8. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187 10.1021/ja800009z
9. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646 10.1021/ja0734086
10. Bickelhaupt, F. M. J. Comput. Chem. 1999, 20, 114 10.1002/(SICI)1096-987X(19990115)20:1<114::AID-JCC12>3.0.CO;2-L
11. Mitchell, R. W.; Dorko, E. A.; Merritt, J. A. J. Mol. Spectrosc. 1968, 26, 197 10.1016/0022-2852(68)90164-1
12. Craig, N. C.; Borick, S. S.; Tucker, T. R.; Xiao, Y.-Z. J. Phys. Chem. 1991, 95, 3549 10.1021/j100162a023
13. Villarreal, J. R.; Laane, J.; Bush, S. F.; Harris, W. C. Spectrochim. Acta 1979, 35, 331 10.1016/0584-8539(79)80188-9
14. Neto, N.; Di Lauro, C.; Castellucci, E.; Califano, S. Spectrochim. Acta 1967, 23, 1763 10.1016/0584-8539(67)80059-X
15. Paton, R. S.; Kim, S. K.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. Angew. Chem., Int. Ed. 2011, 50, 10366 10.1002/anie.201103998
16. Levandowski, B. J.; Houk, K. N. J. Am. Chem. Soc. 2016, 138, 16731 10.1021/jacs.6b10463
17. Staley, S. W.; Howard, A. E.; Strnad, J. T. J. Org. Chem. 1992, 57, 895 10.1021/jo00029a021
18. Rademacher, P. Chem. Rev. 2003, 103, 933 10.1021/cr0100143
19. Levandowski, B. J.; Houk, K. N. J. Org. Chem. 2015, 80, 3530 10.1021/acs.joc.5b00174
20. Levandowski, B. J.; Zou, L.; Houk, K. N. J. Comput. Chem. 2016, 37, 117 10.1002/jcc.24191
21. Liu, S.; Lei, Y.; Qi, X.; Lan, Y. J. Phys. Chem. A 2014, 118, 2638 10.1021/jp411914u
22. Jin, R.; Liu, S.; Lan, Y. RSC Adv. 2015, 5, 61426 10.1039/C5RA10345B
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford CT, 2009.
24. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215 10.1007/s00214-007-0310-x
25. Lan, Y.; Zou, L.; Cao, Y.; Houk, K. N. J. Phys. Chem. A 2011, 115, 13906 10.1021/jp207563h
26. Pieniazek, S. N.; Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7746 10.1002/anie.200801843
27. Fan, L. Y.; Versluis, L.; Ziegler, T.; Baerends, E. J.; Ravenek, W. Int. J. Quantum Chem. 1988, 34, 173 10.1002/qua.560340821
28. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523 10.1021/j100377a021
29. te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931-967 10.1002/jcc.1056
30. Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391 10.1007/s002140050353
31. ADF, SCM Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands, 2016; http://www.scm.com.
32. van Lenthe, E.; Baerends, E. J. J. Comput. Chem. 2003, 24, 1142 10.1002/jcc.10255
33. Franchini, M.; Philipsen, P. H. T.; van Lenthe, E.; Visscher, L. J. Chem. Theory Comput. 2014, 10, 1994 10.1021/ct500172n
34. Becke, A. D. J. Chem. Phys. 1988, 88, 2547 10.1063/1.454033
35. Franchini, M.; Philipsen, P. H. T.; Visscher, L. J. Comput. Chem. 2013, 34, 1819 10.1002/jcc.23323
36. Legault, C. Y. CYLview, 1.0b; Université de Sherbrooke: Sherbrooke, QC, Canada, 2009; http://www.cylview.org.
37. Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755 10.1021/ic50197a006
38. Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558 10.1021/ic50196a034
39. Bickelhaupt, F. M.; Nibbering, N. M. M.; Van Wezenbeek, E. M.; Baerends, E. J. J. Phys. Chem. 1992, 96, 4864 10.1021/j100191a027
40. Bickelhaupt, F. M.; Diefenbach, A.; de Visser, S. P.; de Koning, L. J.; Nibbering, N. M. M. J. Phys. Chem. A 1998, 102, 9549 10.1021/jp9820830
41. Baerends, E. J.; Gritsenko, O. V. J. Phys. Chem. A 1997, 101, 5383 10.1021/jp9703768
42. van Zeist, W.-J.; Fonseca Guerra, C.; Bickelhaupt, F. M. J. Comput. Chem. 2008, 29, 312 10.1002/jcc.20786
43. Bickelhaupt, F. M.; Baerends, E. J. In: Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Wiley-VCH: New York, 2000; Vol. 15, pp 1-86.
44. van Meer, R.; Gritsenko, O. V.; Baerends, E. J. J. Chem. Theory Comput. 2014, 10, 4432 10.1021/ct500727c