Crucial role of elusive isomeric η-complexes in gas-phase electrophilic aromatic alkylations

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 4133-4141

  Marcantoni, Enrico ^a   Roselli, Graziella ^a   Lucarelli, Laura ^a   Renzi, Gabriele ^a   Filippi, Antonello ^b   Trionfetti, Cristiano ^b   Speranza, Maurizio ^b  

^a UNIVERSITY OF CAMERINO   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ISOMERIZATION; PRESSURE EFFECTS; STEREOCHEMISTRY; THERMAL EFFECTS;

ACTIVATION PARAMETERS; GAS PHASE; GAS-PHASE ELECTROPHORESIS; UMIMOLECULAR ISOMERIZATION;

ISOMERS;

3 (4 FLUOROPHENYL)BUTANE; ALKYL GROUP; AROMATIC COMPOUND; BUTANE; CATION; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; GAS; ISOMER; ISOMERIZATION; MOLECULAR STABILITY; PHASE TRANSITION; PRESSURE; PROTON TRANSPORT; RACEMIZATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 18744375191     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050019q     Document Type: Article

References (46)

1. Dewar, M. J. S. J. Chem. Soc. 1946, 406, 777.
2. Herman, J. A.; Harrison, A. G. Org. Mass Spectrom. 1981, 16, 423.
3. Sen Sharma, D. K.; Ikuta, S.; Kebarle, P. Can. J. Chem. 1982, 60, 2325.
4. Grützmacher, H. F.; Filges, U. Int. J. Mass Spectrom. 1985, 64, 193.
5. Bäther, W.; Kuck, D.; Grützmacher, H. F. Org. Mass Spectrom. 1985, 20, 572.
6. Grützmacher, H. F.; Filges, U. Org. Mass Spectrom. 1986, 21, 673.
7. Robin, D.; Prudhomme, P.; Audier, H. E. Adv. Mass Spectrom. 1989, 11a, 614.
8. Holman, R. W.; Gross, M. L. J. Am. Chem. Soc. 1989, 111, 3560.
9. Audier, H. E.; Monteiro, C.; Morgues, P.; Bartomieu, D. Org. Mass Spectrom. 1990, 25, 245.
10. Bartomieu, D.; Audier, H. E.; Monteiro, C.; Denhez, J. P. Org. Mass Spectrom. 1991, 26, 271.
11. Bartomieu, D.; Audier, H. E.; Monteiro, C.; Denhez, J. P. Rapid Commun. Mass Spectrom. 1991, 5, 415.
12. Bowen, R. D. Acc. Chem. Res. 1991, 24, 364.
13. Longevialle, P. Mass Spectrom. Rev. 1992, 11, 157.
14. Morton, T. H. Org. Mass Spectrom. 1992, 16, 423.
15. Berthomieu, D.; Brenner, V.; Ohanessian, G.; Denhez, J. P.; Millié, P.; Audier, H. E. J. Phys. Chem. 1995, 99, 712.
16. Aschi, M.; Troiani, A.; Cacace, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 83.
17. Fornarini, S.; Crestoni, M. E. Acc. Chem. Res. 1998, 31, 827.
18. Aschi, M.; Attinà, M.; Cacace, F. Chem.-Eur. J. 1998, 4, 1535.
19. Holman, R. W.; Eary, T.; Whittle, E.; Gross, M. L. J. Chem. Soc., Perkin Trans. 2 1998, 2187.
20. Kuck, D. Int. J. Mass Spectrom. 2002, 213, 101.
21. Olah, G. A. Acc. Chem. Res. 1971, 4, 240.
22. Olah, G. A.; Lin, H. C. J. Am. Chem. Soc. 1974, 96, 2892.
23. Filippi, A.; Roselli, G.; Renzi, G.; Grandinetti, F.; Speranza, M. Chem.-Eur. J. 2003, 9, 2072.
24. Attinà, M.; Giacomello, P. J. Am. Chem. Soc. 1979,101, 6040.
25. Attinà, M.; De Petris, G.; Giacomello, P. Tetrahedron Lett. 1982, 23, 3525.
26. Attinà, M.; Ricci, A. Tetrahedron Lett. 1991, 32, 6775.
27. Cooke, M. P.; Gopal, D., Jr. J. Org. Chem. 1994, 59, 260.
28. Snowden, R. L.; Linder, S. M.; Muller, B. L.; Schulte-Elte, K. H. Helv. Chim. Acta 1987, 70, 1858.
29. Durman, J.; Elliott, J.; McElroy, A. B.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1237.
30. Hertweck, C.; Moore, B. S. Tetrahedron 2000, 56, 9115.
31. Lewis, N.; McKillop, A.; Taylor, R. J. K.; Watson, R. J. Synth. Commun. 1995, 25, 561.
32. Li, G.; Patel, D.; Hruby, V. J. J. Chem. Soc., Perkin Trans. 1 1994, 3057.
33. Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733.
34. Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 20, 307.
35. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
36. National Institute of Standards and Technology (NIST)-USA, http://webbook.nist.gov/chemistry/.
37. Frish, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, R. E., Jr.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malik, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Raboul, A. G.; Stefaniv, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Nanayakkara, I.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A7; Gaussian, Inc.: Pittsburgh, PA, 1998.
38. Speranza, M.; Cacace, F. J. Am. Chem. Soc. 1977, 99, 3051.
39. Cacace, F.; Speranza, M. J. Am. Chem. Soc. 1976, 98, 7305.
40. +) = 1.9 (n = 1), 0.9 (n = 2). See: Ausloos, P.; Lias, S. G.; Gorden, R., Jr. J. Chem. Phys. 1863, 39, 3341.
41. 3N is calculated according to the following: Su, T.; Chesnavitch, W. J. J. Chem. Phys. 1982, 76, 5183.
42. Hunter, E. P.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
43. -1). It is therefore plausible to take the same proton affinity for the C(1) center of p-fluoro-sec-butylbenzene. Given the vanishingly small effect of the alkyl group on the PA of fluoro-alkylbenzenes at the C-alkyl site, the PA of isomeric fluoro-sec-butylbenzenes is taken to be equal to that of the corresponding ortho, meta, and para positions of fluorobenzene.
44. Denhez, J. P.; Audier, H. E.; Berthomieu, D. Org. Mass Spectrom. 1993, 28, 704.
45. Smith, W. B. J. Phys. Org. Chem. 2002, 15, 347 and references therein.
46. Heidrich, D. Angew. Chem., Int. Ed. 2002, 41, 3208.