Selective infrared photodissociation of protonated para-fluorophenol isomers: Substitution effects in oxonium and fluoronium ions

Journal of Chemical Physics

Volumn 121, Issue 2, 2004, Pages 769-772

  Solcà, Nicola ^a   Dopfer, Otto ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHARGED PARTICLES; CYCLOTRON RESONANCE; ELECTRON TRAPS; ELECTROSTATICS; INFRARED RADIATION; ISOMERS; SPECTROSCOPY; SUBSTITUTION REACTIONS;

DEHYDROFLUORINATION; FLUORONIUM; OXONIUM; PROTONATION;

PHOTODISSOCIATION;

EID: 3242657360     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.1756132     Document Type: Article

References (33)

1. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (Wiley, New York, 1992); L. Stryer, Biochemistry (Freeman, New York, 1996).
2. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (Wiley, New York, 1992); L. Stryer, Biochemistry (Freeman, New York, 1996).
3. V. A. Koptyug, Top. Curr. Chem. 122, 1 (1984); D. M. Brouwer, E. L. Mackor, and C. MacLean, in Carbonium Ions (Wiley, New York, 1970), Vol. II. p. 837; S. M. Hubig and J. K. Kochi, J. Org. Chem. 65, 6807 (2000).
4. V. A. Koptyug, Top. Curr. Chem. 122, 1 (1984); D. M. Brouwer, E. L. Mackor, and C. MacLean, in Carbonium Ions (Wiley, New York, 1970), Vol. II. p. 837; S. M. Hubig and J. K. Kochi, J. Org. Chem. 65, 6807 (2000).
5. V. A. Koptyug, Top. Curr. Chem. 122, 1 (1984); D. M. Brouwer, E. L. Mackor, and C. MacLean, in Carbonium Ions (Wiley, New York, 1970), Vol. II. p. 837; S. M. Hubig and J. K. Kochi, J. Org. Chem. 65, 6807 (2000).
6. M. Okumura, L. I. Yeh, and Y. T. Lee, J. Chem. Phys. 83, 3705 (1985); E. J. Bieske and O. Dopfer, Chem. Rev. (Washington, D.C.) 100, 3963 (2000).
7. M. Okumura, L. I. Yeh, and Y. T. Lee, J. Chem. Phys. 83, 3705 (1985); E. J. Bieske and O. Dopfer, Chem. Rev. (Washington, D.C.) 100, 3963 (2000).
8. N. Solcà and O. Dopfer, Angew. Chem., Int. Ed. 41, 3628 (2002); N. Solcà and O. Dopfer, Chem. Eur. J. 9, 3154 (2003); W. Jones, P. Boissel, B. Chiavarino, M. E. Crestoni, S. Fornarini, J. Lemaire, and P. Maitre, Angew. Chem., Int. Ed. 42, 2057 (2003).
9. N. Solcà and O. Dopfer, Angew. Chem., Int. Ed. 41, 3628 (2002); N. Solcà and O. Dopfer, Chem. Eur. J. 9, 3154 (2003); W. Jones, P. Boissel, B. Chiavarino, M. E. Crestoni, S. Fornarini, J. Lemaire, and P. Maitre, Angew. Chem., Int. Ed. 42, 2057 (2003).
10. N. Solcà and O. Dopfer, Angew. Chem., Int. Ed. 41, 3628 (2002); N. Solcà and O. Dopfer, Chem. Eur. J. 9, 3154 (2003); W. Jones, P. Boissel, B. Chiavarino, M. E. Crestoni, S. Fornarini, J. Lemaire, and P. Maitre, Angew. Chem., Int. Ed. 42, 2057 (2003).
11. N. Solcà and O. Dopfer, Chem. Phys. Lett. 342, 191 (2001); N. Solcà and O. Dopfer, J. Chem. Phys. 120, 10470 (2004).
12. N. Solcà and O. Dopfer, Chem. Phys. Lett. 342, 191 (2001); N. Solcà and O. Dopfer, J. Chem. Phys. 120, 10470 (2004).
13. N. Solcà and O. Dopfer, J. Am. Chem. Soc. 126, 1716 (2004).
14. N. Solcà and O. Dopfer, J. Am. Chem. Soc. 125, 1421 (2003).
15. N. Solcà and O. Dopfer, Angew. Chem., Int. Ed. 42, 1537 (2003).
16. CH/FH). The atoms-in-molecules population analysis was conducted at the B3LYP/6-31G* level. As the cis and trans isomers of 1 and also 2 have similar properties, only the trans isomers of both ions are considered.
17. O. Tishchenko, N. N. Pham-Tran, E. S. Kryachko, and M. T. Nguyen, J. Phys. Chem. A 105, 8709 (2001).
18. B. Bogdanov, D. van Duijn, S. Ingemann, and S. Hammerum, Phys. Chem. Chem. Phys. 4, 2904 (2002).
19. G. A. Olah and Y. K. Mo, J. Org. Chem. 38, 2212 (1973).
20. P. W. Atkins, Physikalische Chemie (VCH, Weinheim, 1996).
21. O. Dopfer, Int. Rev. Phys. Chem. 22, 437 (2003).
22. E. P. L. Hunter and S. G. Lias, J. Phys. Chem. Ref. Data 27, 413 (1998).
23. J. Hrusak, D. Schröder, T. Weiske, and H. Schwarz, J. Am. Chem. Soc. 115, 2015 (1993).
24. N. Solcà, PhD thesis, University of Basel, 2003; N. Solcà and O. Dopfer, (unpublished results).
25. N. Solcà, PhD thesis, University of Basel, 2003; N. Solcà and O. Dopfer, (unpublished results).
26. - in the octopole is larger using M2 than using Ml, leading to a higher noise level in the IRPD spectra recorded with M2.
27. Interestingly, the opposite trend is observed for H→F substitution in the phenol radical cation (Ref. 23).
28. D. C. Hovde, E. R. Keim, and R. J. Saykally, Mol. Phys. 68, 599 (1989); R. B. Le Blanc, J. B. White, and P. F. Bernath, J. Mol. Spectrosc. 164, 574 (1994).
29. D. C. Hovde, E. R. Keim, and R. J. Saykally, Mol. Phys. 68, 599 (1989); R. B. Le Blanc, J. B. White, and P. F. Bernath, J. Mol. Spectrosc. 164, 574 (1994).
30. T. R. Huet, C. J. Pursell, W. C. Ho, B. M. Dinelli, and T. Oka, J. Chem. Phys. 97, 5977 (1992); G. Herzberg, Molecular Spectra and Molecular Structure. II. Infrared and Roman Spectra of Polyatomic Molecules (Krieger, Malabar, 1991).
31. T. R. Huet, C. J. Pursell, W. C. Ho, B. M. Dinelli, and T. Oka, J. Chem. Phys. 97, 5977 (1992); G. Herzberg, Molecular Spectra and Molecular Structure. II. Infrared and Roman Spectra of Polyatomic Molecules (Krieger, Malabar, 1991).
32. E. Fujimaki, A. Fujii, T. Ebata, and N. Mikami, J. Chem. Phys. 110, 4238 (1999).
33. N. Solcà and O. Dopfer, Chem. Phys. Lett. 369, 68 (2003).