Gas-phase reactions of the dichlorocarbene radical cation

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 1999, Pages 2267-2272

  Nelson, Eric D ^a   Tichy, Shane E ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001706522     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903936h     Document Type: Article

References (45)

1. (a) W. Kirmse, Carbene Chemistry, Academic Press, New York, 1971;
2. (b) M. S. Platz, Kinetics and Spectroscopy of Carbenes and Biradicals, Plenum Press, New York, 1990;
3. (c) W. Kirmse, Advances in Carbene Chemistry, U. H. Brinker, Ed., JAI Press, Greenwich, CT, 1994; Vol. 1.
4. (a) D. Bethell and V. D. Parker, Acc. Chem. Res., 1988, 21, 399;
5. (b) V. Parker and D. Bethell, J. Am. Chem. Soc., 1987, 109, 5066.
6. 1 kcal = 4.18 kJ.
7. W. Reuter and S. D. Peyerimhoff, Chem. Phys., 1992, 160, 11.
8. T. Bally, S. Matzinger, L. Truttman, M. S. Platz, A. Admasu, F. Gerson, A. Arnold and R. Schmidlin, J. Am. Chem. Soc., 1993, 115, 7007.
9. D. G. Stoub and J. L. Goodman, J. Am. Chem. Soc., 1997, 119, 11110.
10. (a) J. Berkowitz, J. Chem. Phys., 1978, 69, 3044;
11. (b) C. Wesdemiotis and F. W. McLafferty, Tetrahedron Lett., 1981, 22, 3479.
12. P. C. Burgers, A. A. Mommers and J. L. Holmes, J. Am. Chem. Soc., 1983, 105, 5976.
13. P. C. Burgers, G. A. McGibbon and J. K. Terlouw, Chem. Phys. Lett., 1994, 222, 129.
14. F. A. Wiedmann, J. Cai and C. Wesdemiotis, Rapid Commun. Mass, Spectrom., 1994, 10, 804.
15. G. A. McGibbon, C. A. Kingsmill and J. K. Terlouw, Chem. Phys. Lett., 1994, 222, 539.
16. J. K. Terlouw, J. Wezenberg, P. C. Burgers and J. L. Holmes, J. Chem. Soc., Chem. Commun., 1983, 1121.
17. J. M. Buschek, J. L. Holmes and J. K. Terlouw, J. Am. Chem. Soc., 1987, 109, 7321.
18. D. Sülzle, T. Drewello, B. L. M. van Baar and H. Schwarz, J. Am. Chem. Soc., 1988, 110, 8330.
19. C. Aubry, M. J. Polce, J. L. Holmes, P. M. Mayer and L. Radom, J. Am. Chem. Soc., 1997, 119, 9039.
20. The reactivity of carbene radical anions has been examined. See for example: M. Born, S. Ingemann and N. M. M. Nibbering, J. Chem. Soc., Perkin Trans. 2, 1996, 2537.
21. K. K. Thoen, R. L. Smith, J. J. Nousiainen, E. D. Nelson and H. I. Kenttämaa, J. Am. Chem. Soc., 1996, 118, 8669.
22. L. C. Zeller, J. M. Kennedy, H. I. Kenttämaa and J. E. Campana, Anal. Chem., 1993, 65, 2116.
23. (a) A. G. Marshall, T. C. L. Wang and T. L. Ricca, J. Am. Chem. Soc., 1985, 107, 7893;
24. (b) A. G. Marshall, T. L. Ricca and T. C. L. Wang, U.S. Patent 4,761,545, 1988.
25. (a) P. Lin and H. I. Kenttämaa, Org. Mass Spectrom., 1992, 27, 1155;
26. (b) R. L. Smith, L. J. Chyall, K. M. Stirk and H. I. Kenttämaa, Org. Mass. Spectrom., 1993, 28, 1623;
27. (c) D. T. Leeck, K. M. Stirk, L. C. Zeller, L. K. M. Kiminkinen, L. M. Castro, P. Vainiotalo and H. I. Kenttämaa, J. Am. Chem. Soc., 1994, 116, 3028;
28. (d) R. Li, R. L. Smith and H. I. Kenttämaa, J. Am. Chem. Soc., 1996, 118, 5056.
29. T. Su and W. J. Chesnavich, J. Chem. Phys., 1982, 76, 5183.
30. J. E. Bartmess and R. M. Georgiadis, Vacuum, 1983, 33, 149;
31. (b) K. J. Miller and J. A. Savchik, J. Am. Chem. Soc., 1979, 101, 7206.
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzwewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Repongle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordan, C. Gonzalez and J. A. Pople, Gaussian Inc., Pittsburgh PA, 1995.
33. A. P. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16502.
34. S. G. Lias, Ionization Energy Evaluation in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Eds. W. G. Mallard and P. J. Linstrom, March 1998. National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
35. See for example: K. B. Wiberg, C. M. Hadad, P. R. Rablen and J. Cioslowski, J. Am. Chem. Soc., 1992, 114, 8644.
36. +• by 0.2-0.3 eV.
37. N. A. McAskill, Aust. J. Chem., 1970, 23, 893.
38. (a) R. B. Sharma, D. K. S. Sharma, K. Hiraoka and P. Kebarle, J. Am Chem. Soc., 1985, 107, 3747;
39. (b) J. H. J. Dawson, W. G. Henderson, R. M. O'Malley and K. R. Jennings, Int. J. Mass Spectrom. Ion Phys., 1973, 11, 61;
40. (c) D. K. S. Sharma, S. W. de Höjer and P. Kebarle, J. Am. Chem. Soc., 1985, 107, 3757.
41. P. C. Burgers, J. L. Holmes and J. K. Terlouw, J. Chem. Soc., Chem. Commun., 1982, 642.
42. J. Fossey, D. Lefort and J. Sorba, Free Radicals in Organic Chemistry, Wiley, New York, 1995, Chapter 6.
43. +•) and the allyl cation from A. G. Harrison, Chemical Ionization Mass Spectrometry, 2nd edition, CRC, Ann Arbor, 1992, p. 21; hydride affinities generally correlate well with halide affinities.
44. A. G. Harrison, C. D. Finney and J. A. Sherk, Org. Mass Spectrom., 1971, 5, 1313.
45. W. J. van der Hart, J. Am. Soc. Mass Spectrom., 1999, 10, 575.