Electrophilic aromatic sulfonation with SO 3: Concerted or classic S EAr mechanism?

Journal of the American Chemical Society

Volumn 133, Issue 47, 2011, Pages 19094-19101

  Koleva, Gergana ^a   Galabov, Boris ^a   Kong, Jing ^b   Schaefer, Henry F ^b   Schleyer, Paul Von R ^b  

^a UNIVERSITY OF SOFIA   (Bulgaria)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION ENERGIES; EXPERIMENTAL KINETICS; GASPHASE; NITROMETHANE; NONPOLAR MEDIA; SECOND ORDERS; STRUCTURE COMPUTATION; SULFUR TRIOXIDE; THEORETICAL RESULT; TRANSITION STATE;

ACTIVATION ENERGY; AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; BENZENE; CONTRAST MEDIA; DIMERS; ELECTRONIC STRUCTURE; NAPHTHALENE; REACTION INTERMEDIATES; REACTION KINETICS; SULFUR; TOLUENE;

SULFONATION;

AROMATIC COMPOUND; BENZENE; CARBON TETRACHLORIDE; ELECTROPHILE; NAPHTHALENE; NITROMETHANE; POLYCYCLIC AROMATIC HYDROCARBON; SULFUR OXIDE; SULFUR TRIOXIDE; TOLUENE; TRICHLOROFLUOROMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIELECTRIC CONSTANT; ENERGY; GAS; PHASE TRANSITION; REACTION ANALYSIS; SOLVENT EFFECT; SULFONATION;

CHLOROBENZENES; MOLECULAR STRUCTURE; QUANTUM THEORY; SULFONIC ACIDS; SULFUR OXIDES;

EID: 81855172176     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201866h     Document Type: Article

References (52)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry Reactions, Mechanisms and Structure, 6 th ed.; Wiley: New York, 2006; Chapter 11.
2. Cerfontain, H. Mechanistic Aspects of Aromatic Sulfonation and Desulfonation; Wiley: New York, 1968.
3. Gilbert, E. E. Chem. Rev. 1962, 62, 549-589
4. Gilbert, E. E. Sulfonation and Related Reactions; Interscience Publishers: New York, 1965.
5. Bosscher, J. K.; Cerfontain, H. J. Chem. Soc. B 1968, 1524-1526
6. Lammertsma, K.; Cerfontain, H. J. Chem. Soc., Perkin Trans. 2 1980, 28-32
7. Cerfontain, H. Recl. Trav. Chim. Pays-Bas 1985, 104, 153-165
8. Cerfontain, H. J. A.; Schaasberg, Z. R. H.; Coombes, R. G.; Hadjigeorgion, P.; Tucker, G. P. J. Chem. Soc., Perkin Trans. 2 1985, 5, 659-667
9. Bochkareva, T. P.; Yakovlev, I. P.; Passet, B. V.; Sheiko, M. A. J. Org. Chem. USSR (Engl. Transl.) 1989, 25, 1346-1450
10. Cremlyn, R. J. Chlorosulfonic Acid: A Versatile Reagent; The Royal Society of Chemistry: 2002.
11. Bosscher, J. K.; Cerfontain., H. Tetrahedron 1968, 24, 6543-6555
12. Bosscher, J. K.; Cerfontain, H. Recl. Trav. Chim. Pays-Bas 1968, 87, 873-887
13. 3H still found in most organic chemistry textbooks but is a far more complicated process."
14. -], which has been proposed as the key intermediate in many textbooks, is unlikely to be formed and it follows that the sulfonation process must follow some other path."
15. Katritzky, A. R.; Kim, M. S.; Fedoseyenko, D.; Widyan, K.; Siskin, M.; Francisco, M. Tetrahedron 2009, 65, 1111-1114
16. Morley, J. O.; Roberts, D. W. J. Org. Chem. 1997, 62, 7358-7363
17. Morley, J. O.; Roberts, D. W.; Watson, S. P. J. Chem. Soc., Perkin Trans. 2 2002, 538-542
18. Belen'kii, L. I.; Nesterov, I. D.; Chuvylkin, N. D. Chem. Heterocycl. Compd. (Engl. Transl.) 2006, 42, 1414-1420
19. Chuvylkin, N. D.; Nesterov, I. D.; Belen'kii, L. I. Russ. Chem. Bull. Int. Ed. 2007, 56, 1481-1486
20. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
21. 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
22. Clark, T.; Chandrasekar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301
23. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. Lett. 2008, 112, 1095-1099
24. Jacquemin, D.; Perpète, E. A.; Ciofini, I.; Adamo, C.; Valero, R.; Zhao, Y.; Truhlar, D. J. Chem. Theory Comput. 2010, 6, 2071-2085
25. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2008, 4, 1849-1868
26. Zhao, Y.; Truhlar, D. Acc. Chem. Res. 2008, 41 (2) 157-167
27. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Molecular Orbital Theory; Wiley: New York, 1986.
28. Grimme, S. J. Chem. Phys. 2003, 118, 9095-9102
29. Grimme, S. J. Comput. Chem. 2003, 24, 1529-1537
30. Alecu, I. M.; Zheng, J.; Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2010, 6, 2872-2887
31. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700
32. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
33. Hratchian, H. P.; Schlegel, H. B. In Theory and Applications of Computational Chemistry: The First 40 Years; Dykstra, C. E.; Frenking, G.; Kim, K. S.; Scuseria, G., Eds.; Elsevier: Amsterdam, 2005; pp 195-249.
34. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
35. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361
36. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493
37. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776-4782
38. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991-8998
39. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 523-529
40. Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645-1652
41. Frisch, M. J.; Gaussian 09, Revision-A.02; Gaussian, Inc.: Wallingford, CT, 2009. See Supporting Information for full reference.
42. Skokov, S.; Wheeler, R. A. J. Phys. Chem. A 1999, 103, 4261-4269
43. Bell, R. P. Trans. Faraday Soc. 1959, 55, 1-4
44. Singh, N.; Warshel, A. Proteins 2010, 1705-1723
45. Lelièvre, T.; Rousset, M.; Stoltz, G. Free Energy Computations; Imperial College Press: 2010.
46. Beierlein, F. R.; Michel, J.; Essex, J. W. J. Phys. Chem. B 2011, 115, 4911-4926 and references cited therein.
47. Beierlein, F. R.; Kneale, G. G.; Clark, T. Biophys. J. 2011, 101, 1130-1138 and references cited therein.
48. Knight, J. L.; Brooks, C. L. J. Comput. Chem. 2011, 32, 2909-2923
49. Gillespie, R. J.; Robinson, E. A. Can. J. Chem. 1961, 39, 2189-2200
50. Gillespie, R. J.; Robinson, E. A. Can. J. Chem. 1962, 40, 658-674
51. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746
52. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926