Is the [9]annulene cation a Möbius annulene?

Angewandte Chemie - International Edition

Volumn 48, Issue 52, 2009, Pages 9971-9974

  Bucher, Götz ^a,e   Grimme, Stefan ^b   Huenerbein, Robert ^b   Auer, Alexander A ^c   Mucke, Eva ^d   Köhler, Felix ^d   Siegwarth, Jan ^d   Herges, Rainer ^d  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c MAX PLANCK INSTITUT FÜR EISENFORSCHUNG GMBH   (Germany)

^d UNIVERSITY OF KIEL   (Germany)

^e University of Strathclyde   (United Kingdom)

Author keywords

Annulenes; Aromaticity; Density functional calculations; Laser flash photolysis; M bius arenes

Indexed keywords

AROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY; ISOMERS; PHOTOLYSIS;

A-STABLE; ANNULENES; AROMATICITIES; LASER FLASH PHOTOLYSIS; THEORETICAL CALCULATIONS;

POSITIVE IONS;

EID: 72449173410     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900886     Document Type: Article

References (46)

1. a) H. S. Rzepa, Chem. Rev. 2005, 105, 3697-3715
2. b) R. Herges, Chem. Rev. 2006, 106, 4820-4842.
3. E. Heilbrunner, Tetrahedron Lett. 1964, 5, 1923-1928.
4. S. M. Rappaport, H. S. Rzepa, J. Am. Chem. Soc. 2008, 130, 7613-7619.
5. a) D. Ajami, O. Oeckler, A. Simon, R. Herges, Nature 2003, 426, 819-821
6. b) D. Ajami, K. Hess, F. Köhler, C. Näther, O. Oeckler, A. Simon, C. Yamamoto, Y. Okamoto, R. Herges, Chem. Eur. J. 2006, 12, 5434-5445
7. c) C. Castro, Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney, M. Mauksch, R. Puchta, N. J. R. van Eikema Hommes, P. von R. Schleyer, J. Am. Chem. Soc 2005, 127, 2425-2432
8. d) C. Castro, C. M. Isborn, W. L. Karney, M. Mauksch, P. von R. Schleyer, Org. Lett. 2002, 4, 3431-3434.
9. a) M. Stçpieá, L. Latos-Grazynski, N. Sprutta, P. Chwalisz, L. Szterenberg, Angew. Chem. 2007, 119, 8015-8019;
10. Angew. Chem. Int. Ed. 2007, 46, 7869-7873
11. b) Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z., S. Yoon, K. S. Kim, S. B. Bum, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693-696
12. c) J. K. Park, Z. S. Yoon, M.C. Yoon, K. S. Kim, S. Mori, J.-Y. Shin, A. Osuka, D. Kim, J. Am. Chem. Soc. 2008, 130, 1824-1825
13. d) E. Pacholska-Dudziak, J. Skonieczny, M. Pawlicki, L. Szterenberg, Z. Ciunik, L. LatosGrazynski, J. Am. Chem. Soc. 2008, 130, 6182-6195
14. e) J. Sankar, S. Mori, S. Saito, H, Rath, M. Suzuki, Y. Inokuma, H. Shinokubo, K. S. Kim, Z. S. Yoon, J.-Y. Shin, J. Lim, Y. Matsuzaki, O. Matsushita, A. Muranaka, N. Kobayashi, D. Kim, A. Osuka, J. Am. Chem. Soc. 2008, 130, 13568-13579
15. f) S. Saito, J.-Y. Shin, J. M. Lim, K. S. Kim, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 9803-9806;
16. Angew. Chem. Int Ed 2008, 47, 9657-9660.
17. J. K. Barborak, T.-M. Su, P. von R. Schleyer, G. Boche, G. Schneider, J. Am Chem. Soc. 1971, 93, 279-281.
18. a) A. G. Anastassiou, E. Yakali, J. Am. Chem. Soc. 1971, 93, 3803-3805
19. b) A. G. Anastassiou, E. Yakali, J. Chem. Soc. Chem. Commun. 1972, 531-532.
20. E. Yakali, Dissertation, Syracuse University, NY, 1973.
21. M. Mauksch, V. Gogonea, H. Jiao, P. von R. Schleyer, Angew. Chem. 1998, 110, 2515-2517;
22. Angew. Chem. Int. Ed. 1998, 37, 2395-2397.
23. M. Lundberg, P. E. M. Siegbahn, J. Chem. Phys. 2005, 122, 224103;
24. T. Bally, G. N. Sastry, J. Phys. Chem. A 1997, 101, 7923-7925;
25. P. Mori-Sanchez, A. J. Cohen, W. Yang, J. Chem. Phys. 2006, 125, 201102-1-201102-201104
26. a) R. A. King, T. D. Crawford, J. F. Stanton, H. F. Schaefer III, J. Am. Chem. Soc. 1999, 121, 10788-10793
27. b) C. S. Wannere, K. W. Sattelmeyer, H. F. Schaefer III, P. von R. Schleyer, Angew. Chem. 2004, 116, 4296-4302;
28. Angew. Chem Int. Ed. 2004, 43, 4200-4206.
29. S. N. Pieniazek, F. R. Clemente, K. N. Houk, Angew. Chem. 2008, 120, 7860-7863;
30. Angew. Chem. Int. Ed. 2008, 47, 7746-7749;
31. P. R. Schreiner, Angew. Chem 2007, 119, 4295-4297;
32. Angew. Chem. Int. Ed 2007, 46, 4217-4219.
33. F. Köhler, Dissertation, University of Kiel, 2008.
34. S. Grimme, J. Chem. Phys. 2003, 118, 9095-9102.
35. T. Helgaker, W. Klopper, H. Koch, J. Noga, J. Chem. Phys. 1997, 106, 9639-9646.
36. A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805.
37. G. Bucher, Eur. J. Org. Chem 2001, 2463-2475.
38. Comparison of the experimental transient spectrum of B with the TD-DFT calculated UV/Vis spectrum of the [9]annulene cation 2 is available in the Supporting Information.
39. a) J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209-220
40. b) J. J. P. Stewart, J. Comput. Chem. 1989, 10, 221-264.
41. Gaussian 03, Revision B.04. M. J. Frisch et al., Gaussian Inc., Wallingford, CT, 2004, for full citation see the Supporting Information.
42. TURBOMOLE, version 6.0: R. Ahlrichs et al., Universität Karlsruhe 2009. See http://www.turbomole.com.
43. MOLPRO, version 2006.1, a package of ab initio programs, H.-J. Werner et al. See http://www.molpro.net.
44. M. E. Harding, T. Metzroth, J. Gauss, A. A. Auer, J. Chem. Theory Comput. 2008, 4, 64-74.
45. T. J. Katz, P. J. Garratt, J. Am. Chem. Soc. 1963, 85, 2852-2853.
46. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.