Dissociation routes of protonated toluene probed by infrared spectroscopy in the gas phase

Journal of Physical Chemistry A

Volumn 110, Issue 27, 2006, Pages 8346-8353

  Schröder, Detlef ^a,b   Schwarz, Helmut ^b   Milko, Petr ^a   Roithová, Jana ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; DEHYDROGENATION; HYDROCARBONS; INFRARED SPECTROSCOPY; LIGHT ABSORPTION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; MULTIPHOTON PROCESSES; NEGATIVE IONS;

CYCLOHEPTATRIENE; LINEAR ABSORPTION SPECTRA; PROTONATED TOLUENE; PROTONATION; SKELETAL REARRANGEMENT;

TOLUENE;

EID: 33746465838     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp056962f     Document Type: Article

References (54)

1. IUPAC compendium of chemical technology, 2nd ed.; Blackwell: Glasgow, 1997; see http://www.iupac.org/goldbook/M03819.pdf.
2. Solca, N.; Dopfer, O. Angew. Chem., Int. Ed. 2002, 41, 3628.
3. Jones, W.; Boissel, P.; Chiavarino, B.; Crestoni, M. E.; Fomarini, S.; Lemaire, J.; Maitre, P. Angew. Chem., Int. Ed. 2003, 42, 2057.
4. Ascenzi, D.; Bassi, D.; Franceschi, P.; Tosi, P.; Di Stefano, M.; Rosi, M. J. Chem. Phys. 2003, 119, 8366.
5. Schröder, D.; Loos, J.; Schwarz, H.; Thissen, R.; Dutuit, O. J. Phys. Chem. A 2004, 108, 9931.
6. Kuck, D.; Schneider, J.; Grützmacher, H.-F. J. Chem. Soc., Perkin Trans. 2 1985, 689.
7. (a) Mormann, M.; Salpin, J.-Y.; Kuck, D. J. Eur. J. Mass Spectrom. 1999, 5, 441.
8. (b) Mormann, M.; Kuck, D. J. Mass Spectrom. 1999, 34, 497.
9. Mormann, M.; Kuck, D. Int. J. Mass Spectrom. 2002, 219, 497.
10. Salpin, J.-Y.; Mormann, M.; Tortajada, J.; Nguyen, M.-T.; Kuck, D. Eur. J. Mass Spectrom. 2003, 9, 361.
11. (e) Mormann, M.; Salpin, J.-Y.; Kuck, D. Int. J. Mass Spectrom. 2006, 249, 340.
12. Hippler, H.; Reihs, C.; Troe, J. Z. Phys. Chem. 1990, 167, 1.
13. Brouwer, L. D.; Mueller-Markgraf, W.; Troe, J. J. Phys. Chem. 1988, 92, 4905.
14. Lifshitz, C. Acc. Chem. Res. 1994, 27, 138.
15. (a) Kuck, D. Mass Spectrom. Rev. 1990, 9, 583.
16. (b) Kuck, D. Int. J. Mass Spectrom. 2002, 213, 101.
17. Loos, J.; Schröder, D.; Zummack, W.; Schwarz, H.; Thissen, R.; Dutuit, O. Int. J. Mass Spectrom. 2002, 214, 105.
18. Trage, C.; Schröder, D.; Schwarz, H. Organometallics 2003, 22, 693.
19. Srinivas, R.; Sülzle, D.; Weiske, T.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1991, 107, 368,
20. For details about such corrections, see refs 5 and 12.
21. Maitre, P.; Le Caer, S.; Simon, A.; Jones, W.; Lemaire, J.; Mestdagh, H. ; Heninger, M.; Mauclaire, G.; Boissel, P.; Prazeres, R.; Glotin, F.; Ortega, J.-M. Nucl. Instrum. Methods Phys. Res. A 2003, 507, 541.
22. Le Caer, S. Ph.D. Thesis, Universite Paris-Sud, Orsay, France, 2003.
23. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
24. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
25. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
26. 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.; Baboul, A. G.; 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.11; Gaussian, Inc.: Pittsburgh, PA, 1998.
27. (a) Williams, D. H.; Hvistendahl, G. J. Am. Chem. Soc. 1974, 96, 6755.
28. (b) Hvistendahl, G.; Williams, D. H. J. Chem. Soc., Perkin Trans. 2 1975, 881.
29. Ishikawa, Y.; Yilmaz, H.; Yanai, T.; Nakajima, T.; Hirao, K. Chem. Phys. Lett. 2004, 396, 16 and references therein.
30. Dopfer, O.; Lemaire, J.; Maitre, P.; Chiavarino, B.; Crestoni, M. E.; Fornarini, S. Int. J. Mass Spectrom. 2006, 249, 149.
31. Loos, J.; Schröder, D.; Schwarz, H. J. Org. Chem. 2005, 70, 1073.
32. Derrick, P. J.; Hammerum, S. Can. J. Chem. 1986, 64, 1957.
33. Data converted to 0 K and taken from: Lias, S: G.; Hunter, E. P. L. J. Phys. Chem. Ref. Data 1998, 27, 413.
34. Simon, A.; Jones, W.; Ortega, J.-M.; Boissel, P.; Lemaire, J.; Maitre, P. J. Am. Chem. Soc. 2004, 126, 11666.
35. Oomens, J.; Moore, D. T.; Meijer, G.; von Helden, G. Phys. Chem. Chem. Phys. 2004, 6, 710.
36. Dopfer, O.; Solcà, N.; Lemaire, J.; Maitre, P.; Crestoni, M.-E.; Fornarini, S. J. Phys. Chem. A 2005, 109, 7881.
37. Dunbar, R. C. J. Am. Chem. Soc. 1975, 97, 1382.
38. Ausloos, P. J. Am. Chem. Soc. 1982, 104, 5259.
39. Ignatyev, I. S.; Schaefer, H. F., III. J. Am. Chem. Soc. 2004, 126, 14515.
40. Data converted to 0 K and taken from: (a) NIST Standard Reference Database Number 69, June 2005 Release, National Institute of Standards and Technology, http://webbook.nist.gov/chemistry/.
41. (b) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas-Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data 1998, Suppl. 1, 17.
42. 5 taken from: Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
43. + ions, because the occurrence of hydrogen as well as carbon scrambling in the dissociation clearly demonstrates that the assumption of an intact toluene structure is insufficient.
44. (a) Dunbar, R. C. Int. J. Mass Spectrom. Ion Processes 1990, 100, 423.
45. (b) Van de Guchte, W. J.; Van der Hart, W. J.; De Koning, L. J.; Nibbering, N. M. M.; Dunbar, R. C. Int. J. Mass Spectrom. Ion Processes 1993, 123, 11.
46. Ausloos, P.; Lias, S. G.; Buckley, T. J.; Rodgers E. E. Int. J. Mass Spectrom. Ion Processes 1998, 92, 65.
47. Bouchoux, G.; Yáñez, M.; Mó, O. Int. J. Mass Spectrom. 1999, 185/186/187, 241.
48. Cooks, R. G.; Beynon, J. M.; Caprioli, R. M.; Lester, G. R. Metastable Ions; Elsevier: Dordrecht, The Netherlands, 1973.
49. Moore, D. T.; Oomens, J.; Eyler, J. R.; von Helden, G.; Meijer, G.; Dunbar, R. C. J. Am. Chem. Soc. 2005, 127, 7243.
50. Nee, M. J.; Osterwalder, A.; Neumark, D. M.; Kaposta, C.; Cibiran Uhalte, C.; Xie, T.; Kaledin, A.; Bowman, J. M.; Carter, S.; Asmis, K. R. J. Chem. Phys. 2004, 121, 7259.
51. Lifshitz, C. Eur. J. Mass Spectrom. 2002, 8, 85.
52. Lemaire, J.; Boissel, P.; Heninger, M.; Mauclaire, G.; Bellec, G.; Mestdagh, H.; Simon, A.; Le Caer, S.; Ortega, J. M.; Glotin, F.; Maitre, P. Phys. Rev. Lett. 2002, 89, 273002.
53. (a) Solca, N.; Dopfer, O. Angew. Chem., Int. Ed. 2003, 42, 1537.
54. (b) Solca, N.; Dopfer, O. J. Am. Chem. Soc. 2003, 125, 1421.