Pure and Applied Chemistry

Pure Appl. Chem., 2010, Vol. 82, No. 4, pp. 1011-1024

http://dx.doi.org/10.1351/PAC-CON-09-10-36

Published online 2010-03-19

Structure and stability of the heteroannulated [8–10]circulenes: A quantum-chemical study

References

• 1. V. I. Minkin, M. N. Glukhovtsev, B. Ya. Simkin. Aromaticity and Antiaromaticity. Electronic and Structural Aspects, Wiley-Interscience, New York (1994).
• 2. P. v. R. Schleyer (Ed.). Special issue on “Aromaticity”: Chem. Rev. 101, 1115–1566 (2001). (http://dx.doi.org/10.1021/cr0103221)
• 3. S. C. A. H. Pierrefixe, F. M. Bickelhaupt. Chem.—Eur. J. 13, 6321 (2007). (http://dx.doi.org/10.1002/chem.200700206)
• 4. H. Hopf, G. Maas. Angew. Chem., Int. Ed. 31, 931 (1992).
• 5. C. Domene, P. W. Fowler, L. W. Jenneskens, E. Steiner. Chem.—Eur. J. 13, 269 (2007). (http://dx.doi.org/10.1002/chem.200600507)
• 6. A. Patra, Y. H. Wijsboom, L. J. W. Shimon, M. Bendikov. Angew. Chem., Int. Ed. 46, 8814 (2007). (http://dx.doi.org/10.1002/anie.200703123)
• 7. R. Herges. Chem. Rev. 106, 4820 (2006). (http://dx.doi.org/10.1021/cr0505425)
• 8. R. Salcedo, L. E. Sansores, A. Picazo, L. Sansón. J. Mol. Struct. (Theochem) 678, 211 (2004). (http://dx.doi.org/10.1016/j.theochem.2004.03.020)
• 9. K. K. Baldridge, J. S. Siegel. J. Am. Chem. Soc. 123, 1755 (2001). (http://dx.doi.org/10.1021/ja003383+)
• 10. K. K. Baldridge, J. S. Siegel. J. Am. Chem. Soc. 124, 5514 (2002). (http://dx.doi.org/10.1021/ja017209c)
• 11. X. Zhou, D. A. Hrovat, W. T. Borden. Org. Lett. 10, 893 (2008). (http://dx.doi.org/10.1021/ol703014a)
• 12. K. Yu. Chernichenko, V. V. Sumerin, R. V. Shpanchenko, E. S. Balenkova, V. G. Nenajdenko. Angew. Chem., Int. Ed. 45, 7367 (2006). (http://dx.doi.org/10.1002/anie.200602190)
• 13. K. Yu. Chernichenko, E. S. Balenkova, V. G. Nenajdenko. Mendeleev Commun. 18, 171 (2008). (http://dx.doi.org/10.1016/j.mencom.2008.07.001)
• 14. G. Gahungu, J. Zhang. Phys. Chem. Chem. Phys. 10, 1743 (2008). (http://dx.doi.org/10.1039/b800685g)
• 15. G. Monaco, P. W. Fowler, M. Lillington, R. Zanasi. Angew. Chem., Int. Ed. 46, 1889 (2007). (http://dx.doi.org/10.1002/anie.200604261)
• 16. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople. Gaussian 03, Revision B.03, Gaussian Inc., Pittsburgh (2003).
• 17. A. D. Becke. J. Chem. Phys. 98, 5648 (1993). (http://dx.doi.org/10.1063/1.464913)
• 18. A. D. Becke. J. Chem. Phys. 98, 1372 (1993). (http://dx.doi.org/10.1063/1.464304)
• 19. C. Lee, W. Yang, R. G. Parr. Phys. Rev. B 37, 785 (1988). (http://dx.doi.org/10.1103/PhysRevB.37.785)
• 20. J. B. Foresman, E. Frisch. Exploring Chemistry with Electronic Structure Methods, 2^nd ed., Gaussian, Inc., Pittsburgh (1996).
• 21. B. G. Johnson, P. M. W. Gill, J. A. Pople. J. Chem. Phys. 98, 5612 (1993). (http://dx.doi.org/10.1063/1.464906)
• 22. G. A. Zhurko, D. A. Zhurko. ChemCraft 1.6. <http://www.chemcraftprog.com>.
• 23. J. Emsley. The Elements, Clarendon Press, Oxford (1991).
• 24. J. H. Dopper, D. Oudman, H. Wynberg. J. Org. Chem. 40, 3398 (1975). (http://dx.doi.org/10.1021/jo00911a020)
• 25. O. Bastiansen, L. Hedberg, K. Hedberg. J. Chem. Phys. 27, 1311 (1957). (http://dx.doi.org/10.1063/1.1743999)
• 26. K. H. Claus, C. Krüger. Acta Crystallogr., Sect. C 44, 1632 (1988). (http://dx.doi.org/10.1107/S0108270188005840)
• 27. N. L. Allinger. J. Org. Chem. 27, 443 (1962). (http://dx.doi.org/10.1021/jo01049a024)
• 28. D. Feller, N. C. Craig, A. R. Matlin. J. Phys. Chem. A 112, 2131 (2008). (http://dx.doi.org/10.1021/jp7097334)
• 29. M. Mauksch, V. Gogonea, H. Jiao, P. v. R. Schleyer. Angew. Chem., Int. Ed. 37, 2395 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19980918)37:17<2395::AID-ANIE2395>3.0.CO;2-W)
• 30. T. Kawase, M. Oda. Angew. Chem., Int. Ed. 43, 4396 (2004). (http://dx.doi.org/10.1002/anie.200460050)
• 31. H. S. Rzepa. Chem. Rev. 105, 3697 (2005). (http://dx.doi.org/10.1021/cr030092l)
• 32. L. Farnell, J. Kao, L. Radom, H. F. Schaefer III. J. Am. Chem. Soc. 103, 2147 (1981). (http://dx.doi.org/10.1021/ja00399a001)
• 33. D. R. Price, J. F. Stanton. Org. Lett. 4, 2809 (2002). (http://dx.doi.org/10.1021/ol0200450)
• 34. C. S. Wannere, P. v. R. Schleyer. Org. Lett. 5, 865 (2003). (http://dx.doi.org/10.1021/ol027571b)
• 35. C. Castro, W. L. Karney, C. M. McShane, R. P. Pemberton. J. Org. Chem. 71, 3001 (2006). (http://dx.doi.org/10.1021/jo0521450)
• 36. Z. S. Yoon, A. Osuka, D. Kim. Nat. Chem. 1, 113 (2009). (http://dx.doi.org/10.1038/nchem.172)
• 37. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes. J. Am. Chem. Soc. 118, 6317 (1996). (http://dx.doi.org/10.1021/ja960582d)
• 38. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. v. R. Schleyer. Chem. Rev. 105, 3842 (2005). (http://dx.doi.org/10.1021/cr030088+)
• 39. P. v. R. Schleyer, M. Manoharan, Z. Wang, X. B. Kiran, H. Jiao, R. Puchta, N. J. R. v. E. Hommes. Org. Lett. 3, 2465 (2001). (http://dx.doi.org/10.1021/ol016217v)
• 40. R. Hoffmann, P. v. R. Schleyer, H. F. Schaefer III. Angew. Chem., Int. Ed. 47, 7164 (2008). (http://dx.doi.org/10.1002/anie.200801206)
• 41. T. N. Gribanova, N. S. Zefirov, V. I. Minkin. Dokl. Chem. 426, 105 (2009). (http://dx.doi.org/10.1134/S0012500809050048)