A 6π + 6π potentially antiaromatic zwitterion preferred to a quinoidal structure: Its reactivity toward organic and inorganic reagents

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12246-12256

  Braunstein, Pierre ^a   Siri, Olivier ^a   Taquet, Jean Philippe ^a   Rohmer, Marie Madeleine ^a   Bénard, Marc ^a   Welter, Richard ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; COMPUTATIONAL METHODS; ELECTRIC CHARGE; POSITIVE IONS; REACTION KINETICS; X RAY DIFFRACTION ANALYSIS;

ZWITTERIONS;

AROMATIC COMPOUNDS;

AMPHOLYTE; AROMATIC COMPOUND; BENZOQUINONE DERIVATIVE; BENZOQUINONEIMINE; DICHLOROMETHANE; HYDROGEN; LIGAND; METAL; METHYL GROUP; NITROGEN; PALLADIUM; PROTON; REAGENT; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ATOM; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMISTRY; CONJUGATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY; DIPOLE; ELECTRON; ELECTRON TRANSPORT; ENERGY; MEASUREMENT; MOLECULAR MODEL; MOLECULE; PI ELECTRON; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS; THEORY; X RAY DIFFRACTION;

EID: 0141923171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0354622     Document Type: Article

References (66)

1. Kekulé, A. Bull. Soc. Chim. Fr. (Paris) 1865, 3, 98.
2. Hückel, E. Z. Phys. 1931, 70, 204.
3. See the following reviews: (a) Minkin V. I.; Glukhovtsev M. N.; Simkin B. Y. Aromaticity and Antiaromaticity. Electronic and Structural Aspects; Wiley: New York, 1994.
4. (b) von Ragué Schleyer, P.; Jiao, H. Pure Appl. Chem. 1996, 68, 209.
5. (c) Special issue on aromaticity, Chem. Rev. 2001, 101, No. 5 (guest editor: P. von Ragué Schleyer).
6. (d) Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001.
7. King, R. B. Chem. Rev. 2001, 101, 1119.
8. (a) von Ragué Schleyer, P.; Najafian, K. Inorg. Chem. 1998, 37, 3454.
9. (b) Balakrishnarajan, M. M.; Hoffmann, R. Angew. Chem. Int. Ed. 2003, 42, 3777.
10. Bühl, M.; Hirsch, A. Chem. Rev. 2001, 101, 1153.
11. Hafner, K. Angew. Chem., Int. Ed. Engl. 1964, 3, 165.
12. Pagni, R. M. Tetrahedron 1984, 40, 4161.
13. Prakash, G. K. S.; Rawdah, T. N.; Olah, G. A. Angew. Chem., Int. Ed. Engl. 1983, 22, 401.
14. (a) Nietzki, R.; Hagenbach, E. Ber. Dtsch. Chem. Ges. 1887, 20, 328.
15. (b) Nietzki, R. Ber. Dtsch. Chem. Ges. 1887, 20, 2114.
16. Breslow, R. Angew. Chem., Int. Ed. Engl. 1968, 7, 565.
17. Siri, O.; Braunstein, P.; Rohmer, M.-M.; Bénard, M.; Welter, R. J. Am. Chem. Soc., in press.
18. Wiberg, K. B. Chem. Rev. 2001, 101, 1317.
19. Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. Chem. Rev. 2001, 101, 1501.
20. Kuznetsov, A. E.; Birch, K. A.; Boldyrev, A. I.; Li, X.; Zhai, H.-J.; Wang, L.-S. Science 2003, 300, 622.
21. We thank a referee for raising this question.
22. (a) Bock, H.; Ruppert, K.; Näther, C.; Havlas, Z. Angew. Chem., Int. Ed. Engl. 1991, 30, 1180.
23. (b) Pataï, S.; Rappoport, Z. The Chemistry of the Quinonoid Compounds; Wiley and Sons: New York, 1988; Vols. 1 and 2.
24. (a) Kallmayer, H. J.; Tappe, C. Arch. Pharm. (Weinheim, Ger.) 1985, 318, 569.
25. (b) Kallmayer, H. J.; Tappe, C. Arch. Pharm. (Weinheim, Ger.) 1986, 319, 421.
26. (c) Tindale, C. R. Aust. J. Chem. 1984, 37, 611.
27. (a) Dähne, S.; Leupold, D. Angew. Chem., Int. Ed. Engl. 1966, 5, 984.
28. (b) Kulpe, S. Angew. Chem., Int. Ed. Engl. 1966, 5, 599.
29. Dähne, S.; Leupold, D.; Radeglia, R. J. Pr. Chem. 1972, 314, 525.
30. Tong, L. K. J. In The Theory of the Photographic Process; James, T. H., Ed.; New York, 1977; Chap 12.
31. (a) Corbett, J. F. J. Soc. Cosmt. Chem. 1973, 24, 103.
32. (b) Corbett, J. F. J. Soc. Cosmet. Chem. 1984, 35, 297.
33. (c) Brown, K. C.; Corbett, J. F. J. Soc. Cosmet. Chem. 1979, 30, 191.
34. Zviak, C. Science des traitements capillaires; Masson: Paris, 1988.
35. Siri, O.; Braunstein, P. Chem. Commun. 2002, 208.
36. (a) Beer, L.; Oakley, R. T.; Mingie, J. R.; Preuss, K. E.; Taylor, N. J. J. Am. Chem. Soc. 2000, 122, 7602.
37. (b) Beer, L.; Brusso, J. L.; Cordes, A. W.; Haddon, R. C.; Itkis, M. E.; Kirschbaum, K.; MacGregor, D. S.; Oakley, R. T.; Pinkerton, A. A.; Reed, R. W. J. Am. Chem. Soc. 2002, 124, 9498.
38. Hutchison, K.; Srdanov, G.; Hicks, R.; Yu, H.; Wudl, F.; Strassner, T.; Nendel, M.; Houk, K. N. J. Am. Chem. Soc. 1998, 120, 2989.
39. Note added in proof. A dinickel complex of a benzoquinone has just been reported: Zhang, D.; Jin, G.-X. Organometallics 2003, 22, 2851.
40. Bonnet, A.; Barre, G.; Gilard, P. J. Chim. Phys. 1995, 92, 1823.
41. Rabiller, C.; Ricolleau, G.; Martin, M. L.; Martin, G. J. New J. Chem. 1980, 4, 35.
42. Kirby, A. T.; Komarov, I. V.; Bilenko, V. A.; Davies, J. E.; Rawson, J. M. Chem. Commun. 2002, 2106.
43. Hunter, C. H.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
44. Richeter, S.; Jeandon, C.; Ruppert, R.; Callot, H. J. Chem. Commun. 2001, 91.
45. (a) Richeter, S.; Jeandon, C.; Ruppert, R.; Callot, H. J. Chem. Commun. 2002, 266.
46. (b) Richeter, S.; Jeandon, C.; Gisselbrecht, J.-P.; Ruppert, R.; Callot, H. J. J. Am. Chem. Soc. 2002, 124, 6168.
47. (a) Sawicka, A.; Skurski, P.; Simons, J. Chem. Phys. Lett. 2002, 362, 527.
48. (b) Note added in proof: another theoretical analysis of 8 has been performed by Le, H. T.; Nam, P. C.; Dao, V. L.; Veszprémi, T.; Nguyen, M. T. Mol. Phys. 2003, in press.
49. We thank a referee for his comments.
50. Zhang, R.; Zheng, H.; Shen, J. J. Mol. Struct. 1998, 446, 103.
51. Wudl, F.; Koutentis, P. A.; Weitz, A.; Ma, B.; Strassner, T.; Houk, K. N.; Khan, S. I. Pure Appl. Chem. 1999, 71, 295.
52. User's Guide, Release 1999; Chemistry Department, Vrije Universiteit: Amsterdam, The Netherlands, 1999.
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A. G., C. ; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6: Gaussian, Inc.: Pittsburgh, PA, 1998.
54. Pierpont C. G.; Lange, C. W. Prog. Inorg. Chem. 1994, 41, 331.
55. Min, K. S.; Weyhermüller, T.; Wieghardt, K. J. Chem. Soc., Dalton Trans. 2003, 1126 and refences cited.
56. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973. 2, 41.
57. Fonseca-Guerra, C.; Visser, O.; Snijders, J. G.; Te Velde, G; Baerends, E. J. Methods and Techniques in Computational Chemistry: METECC-95; Clementi E., Corongiu, G., Eds.; STEF: Cagliari, Italy, 1995: p 305.
58. Te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
59. Becke, A. D. Phys. Rev. 1988, A38, 3098.
60. Perdew, J. P. Phys. Rev. 1986, B33, 8882.
61. Perdew, J. P. Phys. Rev. 1986, B34, 7406.
62. Vernooijs, P.; Snijders, J. G.; Baerends, E. J. Slater type basis functions for the whole periodic system; Internal Report; Free University of Amsterdam: The Netherlands, 1981.
63. Snijders, J. G.; Baerends, E. J.; Vernooijs, P. At. Nucl. Tables 1982, 26, 483.
64. Barriol, J. Les moments dipolaires; Gauthier-Villars: Paris, 1957.
65. (a) Kappa CCD Operation Manual; Nonius B. V.; Delft, The Nederlands, 1997.
66. (b) Sheldrick, G. M. SHELXL97, Program for the refinement of crystal structures; University of Gottingen: Germany, 1997.