A theoretical study of substituent effects on allylic ion and ion pair SN2 reactions

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8486-8491

  Streitwieser, A ^a   Jayasree, E G ^a   Leung, S S H ^a   Choy, G S C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION METHODS; ELECTRON TRANSITIONS; ELECTROSTATICS; IONIC CONDUCTION; POLARIZATION;

BENZYLIC SYSTEMS; CONJUGATIVE STABILIZATION; ELECTRON-WITHDRAWING GROUPS; IONIC TRANSITION;

SUBSTITUTION REACTIONS;

ALLYL COMPOUND; HALIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; GEOMETRY; MOLECULAR STABILITY; REACTION ANALYSIS; SUBSTITUTION REACTION; THEORY;

EID: 26844570474     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051277q     Document Type: Article

References (38)

1. Schmatz, S. ChemPhysChem 2004, 5, 600-617.
2. Laerdahl, J. K.; Uggerud, E. Int. J. Mass Spectrom. 2002, 214, 277-314 and references therein.
3. Ren, Y.; Chu, a.-Y. J. Comput. Chem. 2004, 25, 461-467.
4. Hine, J. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1962.
5. Salomaa, P.; Patai, S. The Chemistry of the Carbonyl Group; Wiley: New York, 1966.
6. Streitwieser, A. Chem. Rev. 1956, 56, 571.
7. Streitwieser, A. Solvolytic Displacement Reactions; McGraw-Hill: New York, 1962.
8. Kost, D.; Aviram, K. Tetrahedron Lett. 1982, 23, 4157-4160.
9. Kost, D.; Aviram, K. J. Am. Chem. Soc. 1986, 108, 2006-2013.
10. Wolfe, S.; Mitchell, D. J.; Schlegel, H. B. Can. J. Chem. 1982, 60, 1291.
11. Lee, I.; Kim, C. K.; Lee, B.-S. J. Comput. Chem. 1995, 16, 1045-1054.
12. Lee, I.; Kim, C. K.; Lee, B.-S. J. Phys. Org. Chem. 1995, 8, 473-483.
13. Kormos, B. L.; Cramer, C. J. J. Org. Chem. 2003, 68, 6375-6386.
14. Zipse, H. J. Chem. Soc., Perkin Trans. 2 1997, 2691-2697.
15. 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.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; 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; Gaussian, Inc.: Wallingford, CT, 2004.
16. Lee, I.; Kim, C. K.; Chung, D. S.; Lee, B.-S. J. Org. Chem. 1994, 59, 4490-4494.
17. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301.
18. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265-3269.
19. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
20. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; Wiley: Chichester, 1998; pp 1792-1811.
21. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
22. DeWolfe, R. H.; Young, W. G. Chem. Rev. 1956, 56, 753-901.
23. Shaik, S. S.; Schlegel, H. B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry: The SN2 Mechanism; Wiley. New York, 1992.
24. Shi, Z.; Boyd, R. J. J. Am. Chem. Soc. 1989, 111, 1575-1579.
25. Shi, Z.; Boyd, R. J. J. Am. Chem. Soc. 1990, 112, 6789-6796.
26. Shi, Z.; Boyd, R. J. J. Am. Chem. Soc. 1991, 113, 1072-1076.
27. Hatch, L. F.; Alexander, H. E. J. Am. Chem. Soc. 1949, 71, 1037-1039.
28. Hatch, L. F.; Gordon, L. B.; Russ, J. J. J. Am. Chem. Soc. 1948, 70, 1093-1096.
29. Hatch, L. F.; Nesbit, S. S. J. Am. Chem. Soc. 1951, 73, 358-360.
30. Bordwell, F. G.; Clemens, A. H.; Cheng, J. P. J. Am. Chem. Soc. 1987, 109, 1773-1782.
31. Dodd, J. A.; Brauman, J. I. J. Phys. Chem. 1986, 90, 3559-3562.
32. Jaffe, H. H. Chem. Rev. 1953, 53, 205.
33. McDaniel, D. H.; Brown, H. C. J. Am. Chem. Soc. 1958, 23, 420-427.
34. Wilson, J. M.; Briggs, A. G.; Sawbridge, J. E.; Tickle, P.; Zuckerman, J. J. J. Chem. Soc. A 1970, 1024-1029.
35. Choy, G. S.-C.; Abu-Hasanayn, F.; Streitwieser, A. J. Am. Chem. Soc. 1997, 119, 5013-5019.
36. Harder, S.; Streitwieser, A.; Petty, J. T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 3253-3259.
37. Cayzergues, P.; Georgoulis, C.; Mathieu, G. J. Chim. Phys. 1987, 84, 63-70.
38. Panigrahi, G. P.; Sinha, T. K. Indian J. Chem. 1984, 238, 57-59.