Electrophile affinity: Quantifying reactivity for the bromination of arenes

Journal of Organic Chemistry

Volumn 75, Issue 9, 2010, Pages 2813-2819

  Galabov, Boris ^a   Koleva, Gergana ^a   Schaefer, Henry F ^b   Schleyer, Paul V R ^b  

^a UNIVERSITY OF SOFIA   (Bulgaria)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TOLUENE;

COMPLEX FORMATIONS; ELECTROPHILES; ELECTROPHILIC AROMATIC SUBSTITUTIONS; ELECTROSTATIC POTENTIALS; LIMITING CASE; REGIOSPECIFIC; REGIOSPECIFICITY; SUBSTRATE REACTIVITIES;

BENZENE;

BENZENE DERIVATIVE; ELECTROPHILE; HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHLORINATION; COMPLEX FORMATION; ELECTRICITY;

EID: 77951827761     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902730g     Document Type: Article

References (57)

1. Koleva, G.; Galabov, B.; Wu, I. J.; Schaefer, H. F.; Schleyer, P. v. R. J. Am. Chem. Soc. 2009, 131, 14722-14727
2. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A, Structure and Mechanisms, 4 th ed.; Springer: New York, 2000; Chapter 10.
3. Smith, M. B.; March, J. March's Advanced Organic Chemistry Reactions, Mechanisms and Structure, 6 th ed.; Wiley: New York, 2006; Chapter 11.
4. Stock, L. M.; Brown, H. C. In Advances in Physical Organic Chemistry; Gold, V., Ed;. Academic Press: London, 1963; Vol. 1, p 35.
5. Taylor, R. Electrophilic Aromatic Substitution; John Wiley: New York, 1990.
6. Ridd, J. H. Acc. Chem. Res. 1971, 4, 248-253
7. Wang, D. Z.; Streitwieser, A. Theor. Chem. Acc. 1999, 102, 78-86
8. Streitwieser, A. Molecular Orbital Theory for Organic Chemists; John Wiley and Sons: New York, 1961.
9. Olah, G. A. Acc. Chem. Res. 1971, 4, 240-278
10. Esteves, P. M.; Carneiro, J. E. de M.; Cardoso, S. P.; Barbosa, A. G. H.; Laali, K. K.; Rasul, G.; Prakash, G. K. S.; Olah, G. A. J. Am. Chem. Soc. 2003, 125, 4836-4849
11. Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration. Structure and Mechanisms; VCH Publishers: New York, 1989.
12. Gwaltney, S. R.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 3273-3283
13. Vasiliev, A. V.; Lindeman, S. V.; Kochi, J. K. New J. Chem. 2002, 26, 582-598
14. Fukuzumi, S.; Kochi, J. K. J. Am. Chem. Soc. 1982, 104, 7599-7609
15. De la Mare has stressed the plurality of aromatic substitution mechanisms, depending on the substrate and the conditions. de la Mare, P. B. D. Electrophilic Halogenations; Cambridge University Press: Cambridge, 1976.
16. de la Mare, P. B. D. Acc. Chem. Res. 1974, 7, 361-368
17. Olah, G. A.; Kuhn, S. J.; Flood, S. H.; Hardie, B. A. J. Am. Chem. Soc. 1964, 86, 1039-1044
18. Olah, G. A.; Kuhn, S. J.; Flood, S. H.; Hardie, B. A. J. Am. Chem. Soc. 1964, 86, 1044-1046
19. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
20. Becke, A. D. J. Chem. Phys. 1996, 104, 1040-1046
21. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
22. Curtiss, L. A.; McGrath, M. P.; Blaudeau, J. P.; Davis, N. E.; Binning, R. C., Jr.; Radom, L. J. Chem. Phys. 1995, 103, 6104-6113
23. Clark, T.; Chandrasekar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301
24. Frisch, M. J. et al. Gaussian 03 (Revision-E.01); Gaussian, Inc.: Wallingford CT, 2003.
25. Tomasi, J; Mennucci, B; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
26. Frisch, M. J. et al. Gaussian 09 (Revision-A.01); Gaussian, Inc.: Wallingford CT, 2009.
27. Brown, H. C.; Stock, L. M. J. Am. Chem. Soc. 1957, 79, 1421-1425
28. Dubois, J. E.; Aaron, J. J.; Alcais, P.; Doucet, J. P.; Rothenberg, F.; Uzan, R. J. Am. Chem. Soc. 1972, 94, 6823-6828
29. Rothenberg, F.; Alcais, P.; Dubois, J. E. Bull. Soc. Chim. Fr. 1971, 592-597
30. Aaron, J. J.; Dubois, J. E. Bull. Soc. Chim. Fr. 1971, 603-612
31. Altschuler, L.; Berliner, E. J. Am. Chem. Soc. 1966, 88, 5837-5845
32. Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1957, 79, 5169-5174
33. Brown, H. C.; Wirkkala, R. A. J. Am. Chem. Soc. 1966, 88, 1447-1452
34. Bertolini, O.; Yang, S. S.; Cooks, R. G. Org. Mass Spectrom. 1993, 28, 1313-1322
35. Condon, F. E. J. Am. Chem. Soc. 1948, 70, 1963-1964
36. Marcus, R. A. J. Chem. Phys. 1956, 24, 966-979
37. Reimers, J. R.; Hush, N. S. Electron Transfer in Biology and the Solid State; Oxford University Press: New York, 1989; Chapter 2, pp 27 - 63.
38. Brown, H. C.; Stock, L. M. J. Am. Chem. Soc. 1962, 84, 3298-3306
39. Wilson, E. B. J. Chem. Phys. 1962, 36, 2232-2233
40. Politzer, P. In Chemical Applications of Atomic and Molecular Electrostatic Potentials; Politzer, P.; Truhlar, D. G., Eds.; Plenum Press: New York, 1981; p 7.
41. Bobadova-Parvanova, P.; Galabov, B. J. Phys. Chem. A 1998, 102, 1815-1819
42. Galabov, B.; Bobadova-Parvanova, P. J. Phys. Chem. A 1999, 103, 6793-6799
43. Dimitrova, V.; Ilieva, S.; Galabov, B. J. Phys. Chem. A 2002, 106, 11801-11805
44. Galabov, B.; Cheshmedzhieva, D.; Ilieva, S.; Hadjieva, B. J. Phys. Chem. A 2004, 108, 11457-11462
45. Galabov, B.; Ilieva, S.; Hadjieva, B.; Atanasov, Y.; Schaefer, H. F. J. Phys. Chem. A 2008, 112, 6700-6707
46. Galabov, B.; Nikolova, V.; Wilke, J. J.; Schaefer, H. F.; Allen, W. D. J. Am. Chem. Soc. 2008, 130, 9887-9896
47. Galabov, B.; Ilieva, S.; Schaefer, H. F. J. Org. Chem. 2006, 71, 6382-6387
48. Scrocco, E.; Tomasi, J. Topics in Current Chemistry; Springer-Verlag: Berlin, 1973, p 95.
49. Molecular Electrostatic Potentials; Murray, J. S.; Sen, K., Eds.; Elsevier: Amsterdam, 1996.
50. Murray, J. S.; Politzer, P. Chem. Phys. Lett. 1988, 152, 364
51. Murray, J. S.; Lane, P.; Brinck, T.; Politzer, P. J. Phys. Chem. 1991, 95, 844-848
52. Suresh, C. H.; Gadre, S. R. J. Org. Chem. 1997, 62, 2625-2627
53. Suresh, C. H.; Gadre, S. R. J. Am. Chem. Soc. 1998, 120, 7049-7055
54. Suresh, C. H.; Gadre, S. R. J. Phys. Chem. A 2007, 111, 710-714
55. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746
56. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926
57. Lenoir, D. Angew. Chem., Int. Ed. 2003, 42, 854-857