Evidence for a symmetrical fluoronium ion in solution

Science

Volumn 340, Issue 6128, 2013, Pages 57-60

  Struble, Mark D ^a   Scerba, Michael T ^a   Siegler, Maxime ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE; FLUORONIUM ION; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

CATION; CHEMICAL ANALYSIS; FLUORINE; REACTION KINETICS; THEORETICAL STUDY;

ARTICLE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SOLVOLYSIS; SYNTHESIS;

EID: 84876565621     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1231247     Document Type: Article

References (31)

1. I. Roberts, G. E. Kimball, J. Am. Chem. Soc. 59, 947 (1937).
2. G. A. Olah, Halonium Ions (Wiley, New York, 1975).
3. V. V. Grushin, Chem. Soc. Rev. 29, 315 (2000).
4. R. S. Brown et al ., J. Am. Chem. Soc. 116, 2448 (1994).
5. E. S. Stoyanov, I. V. Stoyanova, F. S. Tham, C. A. Reed, J. Am. Chem. Soc. 132, 4062 (2010).
6. N. Viet, X. Cheng, T. H. Morton, J. Am. Chem. Soc. 114, 7127 (1992).
7. H. Wang, C. E. Webster, L. M. Pérez, M. B. Hall, F. P. Gabbaï, J. Am. Chem. Soc. 126, 8189 (2004).
8. H. J. Böhm et al., ChemBioChem 5, 637 (2004).
9. M. T. Scerba et al., J. Org. Chem. 77, 1605 (2012).
10. R. D. Chambers, Fluorine in Organic Chemistry (Blackwell, Oxford, 2004), pp. 128-129.
11. T. J. Murphy, J. Chem. Educ. 86, 519 (2009).
12. D. E. Sunko, H. Vancik, V. Deljac, M. Milun, J. Am. Chem. Soc. 105, 5364 (1983).
13. See supplementary materials on Science Online.
14. P. R. von Schleyer, C. Maerker, Pure Appl. Chem. 67, 755 (1995).
15. N. Auner, J. Grobe, J. Organomet. Chem. 188, 25 (1980).
16. J. D. Sunderhaus, H. Lam, G. B. Dudley, Org. Lett. 5, 4571 (2003).
17. S. Jaime-Figueroa, L. J. Kurz, Y. Z. Liu, R. Cruz, Spectrochim. Acta A 56, 1167 (2000).
18. F. B. Mallory, C. W. Mallory, W. M. Ricker, J. Am. Chem. Soc. 97, 4770 (1975).
19. F. B. Mallory, C. W. Mallory, W. M. Ricker, J. Org. Chem. 50, 457 (1985).
20. Gaussian 09, Revision A.1 (Gaussian Inc., Wallingford, CT, 2009).
21. Spartan '06 Program (Wavefunction Inc., Irvine, CA).
22. H. J. Schneider, D. Heiske, J. Am. Chem. Soc. 103, 3501 (1981).
23. A. Hassner, F. P. Boerwinkle, A. B. Lavy, J. Am. Chem. Soc. 92, 4879 (1970).
24. T. Yin, W. T. Borden, J. Org. Chem. 51, 2285 (1986).
25. X. Creary, S. R. McDonald, J. Org. Chem. 50, 474 (1985).
26. A. D. Allen, V. M. Kanagasabapathy, T. T. Tidwell, J. Am. Chem. Soc. 107, 4513 (1985).
27. F. W. Wehrli, A. P. Marchand, S. Wehrli, Interpretation of Carbon 13 NMR Spectra (Wiley, New York, ed. 2, 1983), pp. 192-193.
28. T. Bentley, G. E. Carter, J. Am. Chem. Soc. 104, 5741 (1982).
29. H. J. Schneider, G. Schmidt, Chem. Ber. 119, 65 (1986).
30. D. N. Kevill, S. W. Anderson, J. Org. Chem. 50, 3330 (1985).
31. T. Svensson, S. Winstein, J. Am. Chem. Soc. 94, 2336 (1972).