Why are perfluorocyclobutadiene and some other (CF)nq rings non-planar?

Organic Letters

Volumn 12, Issue 4, 2010, Pages 768-771

  Wu, Judy I ^a   Evangelista, Francesco A ^b   Von Ragué Schleyer, Paul ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 76849085496     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902866n     Document Type: Article

References (25)

1. Petersson, E. J.; Fanuele, J. C.; Nimios, M. R.; Lemal, D. M.; Ellison, G. B.; Radziszewski, J. G. J. Am. Chem. Soc. 1997, 119, 11122-11123.
2. 4).
3. Koehler, F.; Herges, R.; Stanger, A. J. Phys. Chem. A 2007, 111, 5116-5118.
4. Seal, P.; Chakrabarti, S. J. Phys. Chem. A 2007, 111, 5119-5121.
5. Hammons, J. H.; Coolidge, M. B.; Borden, W. T. J. Phys. Chem. 1990, 94, 5468-5470.
6. Almenningen, A.; Bastiansen, O.; Seip, R.; Hans, M. Acta Chem. Scand. 1964, 18, 2115-2124.
7. Carlos, J. L., Jr.; Carl, R. R., Jr.; Bauer, S. H, J. Chem. Soc. Faraday Trans. 2 1974, 70, 177-187.
8. 4, is not direct evidence for SOTJE,
9. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; Hommes, N. J. r. V. E. J. Am. Chem. Soc. 1996, 118, 6317-6318.
10. Corminboeuf, C.; Heine, T.; Seifert, G.; Schleyer, P. v. R. Phys. Chem. Chem. Phys. 2004, 6, 273-276.
11. Wheeler S. E. HFSmol; University of Georgia: Athens, GA, 2008.
12. xx = -7.6 ppm). Although zz is the conventional outof-plane designation, it does not always represent the perpendicular tensor component in the NICS output, since the "xx, yy, and zz" assignment depends on the orientation of the molecule.
13. NBO 5.X. Glendening, E. D. Badenhoop, J. K. ReedA. E. Carpenter, J. E. Bohmann, J. A. Morales, C. M., WeinholdF. Theoretical Chemistry Institute; University of Wisconsin: Madison, WI, 2003.
14. Reed, A. E.; Curtis, L. A.; Wienhold, F. Chem. Rev. 1988, 88, 899-926.
15. Wiberg, K. B.; Murcko, M. A. J. Mol. Struct. (THEOCHEM) 1988, 169, 355-365.
16. Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1987, 109, 7362-7373.
17. Evangelista, F. A.; Allen, W. D.; Schaefer, H. F. J. Chem. Phys. 2007, 127, 24102-24119.
18. Balci, M.; McKee, M. L.; Schleyer, P. v. R. J. Phys. Chem. 2000, 104, 1246-1255.
19. * (see page 3). There is no kinetic energy difference!
20. Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Org. Lett. 2006, 8, 863-866.
21. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842-3888.
22. Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669-12670.
23. 4, perfluorination of benzene has essentially no effect on either its geometry or aromaticky: Wu, J. I.; Puhlhofer, F. G.; Schleyer, P. v. R.; Puchta, R.; Kiran, B.; Mauksch, M.; Hommes, N. J. R. v.; Alkorta, E. L; Elguero, J. J. Phys. Chem. A 2009, 113, 6789-6794.
24. Vysotsky, V. P.; Salnikov, G. E.; Shchegoleva, L. N. Int. J. Quantum Chem. 2004, 100, 469-476.
25. Shchegoleva, L. N.; Beregovaya, I. V.; Schastnev, P. V. Chem. Phys. Lett. 1999, 312, 325-332.