The [12]annulene global minimum

Journal of Organic Chemistry

Volumn 73, Issue 4, 2008, Pages 1532-1535

  Braten, Miles N ^a   Castro, Claire ^a   Herges, Rainer ^b   Köhler, Felix ^b   Karney, William L ^a  

^a UNIVERSITY OF SAN FRANCISCO   (United States)

^b UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; CHEMICAL SHIFT; CONFORMATIONS; ISOMERS;

ANNULENE ISOMER; CONFORMATIONAL AUTOMERIZATION;

HYDROCARBONS;

ANNULENE DERIVATIVE;

ARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 39349093350     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702412d     Document Type: Article

References (21)

1. For a recent review, see: Spitler, E. L.; Johnson, C. C., II; Haley, M. M. Chem. Rev. 2006, 106, 5344.
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3. (b) Castro, C.; Karney, W. L.; Valencia, M. A.; Vu, C. M. H.; Pemberton, R. P. J. Am. Chem. Soc. 2005, 127, 9704.
4. (c) Castro, C.; Isborn, C. M.; Karney, W. L.; Mauksch, M.; Schleyer, P. v. R. Org. Lett. 2002, 4, 3431-3434.
5. (d) Eichberg, M. J.; Houk, K. N.; Lehmann, J.; Leonard, P. W.; Märker, A.; Norton, J. E.; Sawicka, D.; Vollhardt, K. P. C.; Whitener, G. D.; Wolff, S. Angew. Chem., Int. Ed. 2007, 46, 6894.
6. (a) Gard, M. N.; Reiter, R. C.; Stevenson, C. D. Org. Lett. 2004, 6, 393.
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8. For a review of [4n]annulenes, see: Wiberg, K. B. Chem. Rev. 2001, 101, 1317.
9. (a) Oth, J. F. M.; Röttele, H.; Schröder, G. Tetrahedron Lett. 1970, 61.
10. (b) Oth, J. F. M.; Gilles, J.-M.; Schröder, G. Tetrahedron Lett. 1970, 67 .
11. See footnote 29 of ref 2b. The relative energy of 5 was incorrectly reported in that paper as being -2.6 kcal/mol.
12. (a) For the use of BHHLYP geometries when computing magnetic criteria for annulenes, and for obtaining correct relative ordering, see ref 2a and: Wannere, C. S.; Sattelmeyer, K. W.; Schaefer, H. F., III; Schleyer, P. v. R. Angew. Chem., Int. Ed. 2004, 43, 4200.
13. (b) For the use of CCSD-(T)/cc-pVDZ energies on DFT geometries of [12]annulenes, see ref 2a and references therein.
14. All calculations were performed using Gaussian 03: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
15. Oth, J. F. M.; Schröder, G. J. Chem Soc. (B) 1971, 904.
16. 4 symmetric [16]annulene are +10.6 and +49.6 cgs·ppm, respectively. MSEs were computed as in ref 2b. For [16]annulene, see: Johnson, S. M.; Paul, I. C.; King, G. S. D. J. Chem. Soc. (B) 1970, 643.
17. Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Chem. Rev. 2005, 105, 3758.
18. Oth, J. F. M. Pure Appl. Chem. 1971, 25, 573.
19. 2- would need to be clarified to understand peak averaging on the NMR time scale. This work is currently being investigated.
20. Pemberton, R. P.; McShane, C. M.; Castro, C.; Karney, W. L. J. Am. Chem. Soc. 2006, 128, 16692.
21. Of the different electrocyclization pathways conceivable for 5, those involving six electrons are not feasible, due to the difficulty of attaining the necessary conformation.