Water-catalyzed interconversion of conventional and distonic radical cations: Methanol and methyleneoxonium radical cations

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6299-6300

  Gauld, James W ^a   Audier, Henri ^b   Fossey, Jacques ^b   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

METHANOL; RADICAL;

ARTICLE; DRUG STRUCTURE; MOLECULAR DYNAMICS;

EID: 0030040082     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960924f     Document Type: Article

References (24)

1. (a) Bouma, W. J.; Nobes, R. H.; Radom, L. J. Am. Chem. Soc. 1982, 104, 2929.
2. (b) Yates, B. F.; Bouma, W. J.; Radom, L. Tetrahedron 1986, 42, 6225.
3. (c) Yates. B. F.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250.
4. (d) Ma, N. L.; Smith, B. J.; Pople, J. A.; Radom, L. J. Am. Chem. Soc. 1991, 113, 7903.
5. (e) Ma, N. L.; Smith, B. J.; Radom, L. J. Phys. Chem. 1992, 96, 5804.
6. (f) Gauld, J. W.; Radom, L. J. Phys. Chem. 1994, 98, 777.
7. (a) Bouma, W. J.; MacLeod, J. K.; Radom, L. J. Am. Chem. Soc. 1982, 104, 2930.
8. (b) Holmes, J. L.; Lossing, F. P.; Terlouw, J. K.; Burgers, P. C. J. Am. Chem. Soc. 1982, 104, 2931.
9. For leading references, see: (a) Radom, L.; Bouma, W. J.; Nobes, R. H.; Yates, B. F. Pure Appl. Chem. 1984, 56, 1831. (b) Schwarz, H. Shitsuryo Bunseki 1984, 32, 3. (c) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 23. (d) Stirk, K. M.; Kiminkinen, L. K. M.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
10. For leading references, see: (a) Radom, L.; Bouma, W. J.; Nobes, R. H.; Yates, B. F. Pure Appl. Chem. 1984, 56, 1831. (b) Schwarz, H. Shitsuryo Bunseki 1984, 32, 3. (c) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 23. (d) Stirk, K. M.; Kiminkinen, L. K. M.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
11. For leading references, see: (a) Radom, L.; Bouma, W. J.; Nobes, R. H.; Yates, B. F. Pure Appl. Chem. 1984, 56, 1831. (b) Schwarz, H. Shitsuryo Bunseki 1984, 32, 3. (c) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 23. (d) Stirk, K. M.; Kiminkinen, L. K. M.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
12. For leading references, see: (a) Radom, L.; Bouma, W. J.; Nobes, R. H.; Yates, B. F. Pure Appl. Chem. 1984, 56, 1831. (b) Schwarz, H. Shitsuryo Bunseki 1984, 32, 3. (c) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 23. (d) Stirk, K. M.; Kiminkinen, L. K. M.; Kenttämaa, H. I. Chem. Rev. 1992, 92, 1649.
13. (a) Mourges, P.; Audier, H. E.; Leblanc, D.; Hammerum, S. Org. Mass Spectrom. 1993, 28. 1098.
14. (b) Audier, H. E.; Leblanc, D.; Mourges, P.; McMahon, T. B.; Hammerum, S. J. Chem. Soc., Chem. Commun. 1994, 2329.
15. Bohme, D. K. Int. J. Mass Spectrom. Ion Proc. 1992, 115, 95.
16. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
17. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
18. We have used QCISD/6-31G(d,p) optimized geometries (rather than the standard G2 MP2/6-31G(d) geometries) and scaled MP2/6-311G(d,p) vibrational frequencies (rather than the standard G2 HF/6-31G(d) frequencies) in the present work. The scale factor is 0.9496: Scott, A. P.; Radom, L. To be published. Similar results are obtained if the G2 calculations are based on MP2/6-31G(d,p) optimized geometries.
19. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92, Gaussian Inc.: Pittsburgh, PA, 1992.
20. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J, B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Gaussian Inc., Pittsburgh, PA, 1995.
21. (a) Holmes, J. L.; Lossing, F. P.; Terlouw, J. K.; Burgers, P. C. Can. J. Chem. 1983, 61, 2305.
22. (b) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard. W. G. J. Phys. Chem. Ref. Data, Suppl. 1988, 17.
23. Burcl, R.; Hobza, P. Theor. Chim. Acta 1993, 87, 97.
24. Detailed results will be presented elsewhere: Gauld, J. W.; Radom, L. To be published.