Rearrangement and hydrogen scrambling pathways of the toluene radical cation: A computational study

Journal of Physical Chemistry A

Volumn 112, Issue 20, 2008, Pages 4694-4702

  Norberg, Daniel ^a   Larsson, Per Erik ^b   Salhi Benachenhou, Nessima ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b SINTEF MATERIALS AND CHEMISTRY   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENES; HYDROGEN; MECHANISMS; MINE FLOODING; TOLUENE;

AB-INITIO; BASIS SETS; CCSD; COMPUTATIONAL STUDIES; CYCLOHEPTATRIENE; DENSITY-FUNCTIONAL; HYDROGEN DISSOCIATION; HYDROGEN SCRAMBLING; RADICAL CATION; RADICAL CATIONS; REACTION BARRIERS; REARRANGEMENT REACTIONS;

POSITIVE IONS;

EID: 53349142739     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp711166d     Document Type: Article

References (25)

1. Lifshitz, C. Acc. Chem. Res. 1994, 27, 138.
2. Dunbar, C. D. J. Am. Chem. Soc. 1975, 97, 1382.
3. Ausloos, P. J. Am. Chem. Soc. 1982, 104, 5259.
4. Meyer, F.; Harrison, A. G. J. Am. Chem. Soc. 1964, 86, 4757.
5. Baer, T.; Morrow, J. C.; Shao, J. D.; Olesik, S. J. Am. Chem. Soc. 1988, 110, 5633.
6. Huang, F.-S.; Dunbar, R. C. Int. J. Mass. Spectrom. Ion Processes 1991, 109, 151.
7. Choe, J. C. J. Phys. Chem. A 2006, 110, 7655.
8. Rylander, P. N.; Meyerson, S.; Grubb, H. M. J. Am. Chem. Soc. 1957, 79, 842.
9. Baldwin, M. A.; McLafferty, F. W.; Jerina, D. M. J. Am. Chem. Soc. 1975, 97, 6169.
10. Howe, I.; McLafferty, F. W. J. Am. Chem. Soc. 1971, 93, 99. and references therein.
11. Hoffman, M. K. Z. Naturforsch. 1974, 29a, 1077. and references therein.
12. Kless, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 4524. and references therein.
13. Dewar, M. J. S.; Landman, D. J. Am. Chem. Soc. 1977, 99, 2446.
14. Lifshitz, C.; Gotkis, Y.; Ioffe, A.; Laskin, J.; Shaik, S. Int. J. Mass. Spectrom. Ion Processes 1993, 125, R7.
15. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17 (Suppl. 1).
16. Grützmacher, H.-F.; Harting, N. Eur. J. Mass. Spectrom. 2003, 9, 327.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
18. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. Molekel-4.3; Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
19. In fact, using a constrained optimization scan at the B3LYP/6-311+G(d,p) level of theory, we estimated the barrier for the methyl rotation in 1 to be 0.02 kcal/mol.
20. Feldman, V. I.; Sukhov, F.; Orlov, A.; Kadam, R.; Itagaki, Y.; Lund, A. Phys. Chem. Chem. Phys. 2000, 2, 29.
21. Symons, M. C. R.; Harris, L. J. Chem. Res., Synop. 1982, 268.
22. Faucitano, A.; Buttafava, A.; Martinotti, F. Radiat. Phys. Chem. 1995, 45, 45.
23. See, for example, Rogowska, A.; Kuhl, S.; Schneider, R.; Walcarius, A.; Champagne, B. Phys. Chem. Chem. Phys. 2007, 9, 828.
24. Norberg, D.; Larsson, P.-E.; Salhi-Benachenhou, N. Org. Biomol. Chem. 2006, 4, 4241.
25. Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. Chem. Phys. Lett. 1991, 182, 225.