Protonation of gas-phase aromatic molecules: IR spectrum of the fluoronium isomer of protonated fluorobenzene

Journal of the American Chemical Society

Volumn 125, Issue 5, 2003, Pages 1421-1430

  Solca, Nicola ^a   Dopfer, Otto ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

SUPERSONIC PLASMA EXPANSION;

BOND STRENGTH (CHEMICAL); DISSOCIATION; INFRARED RADIATION; ISOMERS; POSITIVE IONS;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; FLUOROBENZENE;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; DIPOLE; DISSOCIATION; ENERGY TRANSFER; GAS; INFRARED SPECTROSCOPY; IONIZATION; ISOMER; PROTON TRANSPORT; QUANTUM CHEMISTRY; VIBRATION;

FLUOROBENZENES; GASES; PROTONS; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; THERMODYNAMICS;

EID: 0037419776     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021036p     Document Type: Article

References (71)

1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Plenum Press: New York, 1995.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley: New York, 1992.
3. Olah, G. A.; White, A. M.; O'Brien, D. H. Chem. Rev. 1970, 70, 561.
4. Perkampus, H. H.; Baumgarten, E. Angew. Chem., Int. Ed. Engl. 1964, 3, 776.
5. Koptyug, V. A. Top. Curr. Chem. 1984, 122, 1.
6. Brouwer, D. M.; Mackor, E. L.; MacLean, C. Arenonium Ions. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1970; Vol. II.
7. Fornarini, S. Mass Spectrom. Rev. 1997, 15, 365.
8. Fornarini, S.; Crestoni, M. E. Acc. Chem. Res. 1998, 31, 827.
9. Kuck, D. Mass Spectrom. Rev. 1990, 9, 583.
10. Mason, R. S.; Williams, C. M.; Anderson, P. D. J. J. Chem. Soc., Chem. Commun. 1995, 1027.
11. Solcà, N.; Dopfer, O. Angew. Chem., Int. Ed. 2002, 41, 3628.
12. Bieske, E. J.; Dopfer, O. Chem. Rev. 2000, 100, 3963.
13. Solcà, N.; Dopfer, O. Chem. Phys. Lett. 2001, 342, 191.
14. Yeh, L. I.; Okumura, M.; Myers, J. D.; Price, J. M.; Lee, Y. T. J. Chem. Phys. 1989, 91, 7319.
15. Nizkorodov, S. A.; Roth, D.; Olkhov, R. V.; Maier, J. P.; Dopfer, O. Chem. Phys. Lett. 1997, 278, 26.
16. Olkhov, R. V.; Dopfer, O. Chem. Phys. Lett. 1999, 314, 215.
17. Hrusak, J.; Schröder, D.; Weiske, T.; Schwarz, H. J. Am. Chem. Soc. 1993, 115, 2015.
18. Olah, G. A.; Mo, Y. K. J. Org. Chem. 1973, 38, 3212.
19. Szulejko, J. E.; Hrusak, J.; McMahon, T. B. J. Mass Spectrom. 1997, 32, 494.
20. Hudlicky, M. Chemistry of Organic Fluorine Compounds; Prentice Hall: New York, 1992.
21. Plenio, H. Chem. Rev. 1997, 97, 3363.
22. Speranza, M.; Cacace, F. J. Am. Chem. Soc. 1977, 99, 3051.
23. Cacace, F.; Speranza, M. J. Am. Chem. Soc. 1976, 98, 7299.
24. Speranza, M.; Sefcik, M. D.; Henis, J. M. S.; Gaspar, P. P. J. Am. Chem. Soc. 1977, 99, 5583.
25. Mason, R.; Milton, D.; Harris, F. J. Chem. Soc., Chem. Commun. 1987, 1453.
26. Tkaczyk, M.; Harrison, A. G. Int. J. Mass Spectrom. Ion Processes 1990, 100, 133.
27. Tkaczyk, M.; Harrison, A. G. Int. J. Mass Spectrom. Ion Processes 1994, 132, 73.
28. Mason, R. S.; Parry, A. J.; Milton, D. M. P. J. Chem. Soc., Faraday Trans. 1994, 90, 1373.
29. Schröder, D.; Oref, I.; Hrusak, J.; Weiske, T.; Nikitin, E. E.; Zummack, W.; Schwarz, H. J. Phys. Chem. A 1999, 103, 4609.
30. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
31. Oomens, J.; Meijer, G.; von Helden, G. J. Phys. Chem. A 2001, 105, 8302.
32. Nizkorodov, S. A.; Dopfer, O.; Ruchti, T.; Meuwly, M.; Maier, J. P.; Bieske, E. J. J. Phys. Chem. 1995, 99, 17118.
33. Guelachvili, G.; Rao, K. N. Handbook of Infrared Standards; Academic Press: London, 1993.
34. Camy-Peyret, C.; Flaud, J. M.; Guelachvili, G.; Amiot, C. Mol. Phys. 1973, 26, 825.
35. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
36. Le Blanc, R. B.; White, J. B.; Bernath, P. F. J. Mol. Spectrosc. 1994, 164, 574.
37. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
38. Although the energies are corrected for BSSE, the equilibrium geometries are not.
39. Chalasinski, G.; Szczesniak, M. M. Chem. Rev. 1994, 94, 1.
40. Bader, R. F. W.; Chang, C. J. Phys. Chem. 1989, 93, 5095.
41. Maksic, T. B.; Kovacevic, B.; Kovacek, D. J. Phys. Chem. A 1997, 101, 7446.
42. Wiberg, K. B.; Rablen, P. R. J. Org. Chem. 1998, 63, 3722.
43. Dopfer, O., unpublished results.
44. Olah, G. A.; Staral, J. S.; Asenicio, G.; Liang, G.; Forsyth, D. A.; Mateescu, G. D. J. Am. Chem. Soc. 1978, 100, 6299.
45. Tishchenko, O.; Pham-Tran, N. N.; Kryachko, E. S.; Nguyen, M. T. J. Phys. Chem. A 2001, 105, 8709.
46. Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2000, 39, 2014.
47. Solcà, N.; Dopfer, O. Chem. Phys. Lett. 2001, 347, 59.
48. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1984, 13, 695.
49. Varsanyi, G. Assignments for Vibrational Spectra of 700 Benzene Derivatives; Adam Hilger: London, 1974.
50. Gray, C. G.; Gubbins, K. E. Theory of Molecular Fluids; Clarendon: Oxford, 1984; Vol. 1.
51. +.
52. Schäfer, E.; Saykally, R. J. J. Chem. Phys. 1984, 81, 4189.
53. Glaser, R.; Horan, C. J. J. Org. Chem. 1995, 60, 7518.
54. NIST Chemistry Web Book; http:/webbook.nist.gov, 2001.
55. Harrison, A. G.; Lin, P. H. Can. J. Chem. 1975, 53, 1314.
56. Abramson, F. P.; Furtell, J. H. J. Chem. Phys. 1966, 45, 1925.
57. Chong, S. L.; Franklin, J. L. J. Chem. Phys. 1971, 55, 641.
58. Huntress, W. T. J. Chem. Phys. 1972, 56, 5111.
59. Weiner, J.; Smith, G. P. K.; Saunders, M.; Cross, R. J. J. Am. Chem. Soc. 1973, 95, 4115.
60. Lee, H. S.; Bierbaum, V. M.; DePuy, C. H. Int. J. Mass Spectrom. Ion Processes 1997, 167/168, 587.
61. Hovde, D. C.; Keim, E. R.; Saykally, R. J. Mol. Phys. 1989, 68, 599.
62. Nizkorodov, S. A.; Meuwly, M.; Maier, J. P.; Dopfer, O.; Bieske, E. J. J. Chem. Phys. 1998, 108, 8964.
63. Ayotte, P.; Weddle, G. H.; Kim, J.; Johnson, M. A. J. Am. Chem. Soc. 1998, 120, 12361.
64. In fact, the observed cross section corresponds to the product of absorption and dissociation cross sections. It is assumed that quantitative dissociation of metastable levels above the lowest dissociation limit can occur on the time scale of the experiment (that is, the flight time through the octopole). Thus, the observed cross section is proportional to the absorption cross section, as the dissociation cross section is roughly constant.
65. Hrusak, J.; Schröder, D.; Iwata, S. J. Chem. Phys. 1997, 106, 7541.
66. Lorquet, J. C.; Lorquet, A. J. J. Phys. Chem. A 2001, 105, 3719.
67. Baer, T.; Hase, W. L. Unimolecular Reaction Dynamics; Oxford University Press: New York, 1996.
68. Miller, R. E. Science 1988, 240, 447.
69. Ewing, G. E. J. Phys. Chem. 1987, 91, 4662.
70. Olkhov, R. V.; Nizkorodov, S. A.; Dopfer, O. J. Chem. Phys. 1998, 108, 10046.
71. Hiraoka, K.; Kudaka, I.; Yamabe, S. Chem. Phys. Lett. 1991, 178, 103.