1- and 2-adamantyl radicals and cations in the gas phase: Thermochemistry and mass spectrometry

Journal of Physical Chemistry A

Volumn 102, Issue 8, 1998, Pages 1389-1393

  Aubry, Christiane ^a   Holmes, John L ^a   Walton, John C ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; ELECTRON ENERGY LEVELS; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

ADAMANTYL CATIONS; ADAMANTYL RADICALS; POTENTIAL ENERGY SURFACE; THERMOCHEMISTRY;

AROMATIC COMPOUNDS;

EID: 0032001332     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9728924     Document Type: Article

References (42)

1. Fort, R. C. Adamantane, the Chemistry of Diamond Molecules; Marcel Dekker: New York, 1976.
2. For a review, see: Tominaga, K.; Haga, M. Chem. Econ. Eng. Rev. 1986, 10, 23.
3. (a) Krusic, P. J.; Rettig, T. A.; Schleyer, P.v.R. J. Am. Chem. Soc. 1972, 94, 995.
4. (b) Kira, M.; Watanabe, M.; Ichinose, M.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 3762.
5. Olah, G. A.; Prakash, G. K. S.; Shih, J. G; Krishnamurthy, V. V.; Matuscu, G. D.; Liang, G.; Sipos, G.; Buss, V.; Gund, T. M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1985 107, 2764.
6. Vogel, P.; Saunders, M.; Thielecke, W.; Schleyer, P.v.R. Tetrahedron Lett. 1971, 18, 1429.
7. Adams, D. R.; Bailey, P. D.; Collier, I. D.; Leah, S. A. H.; Ridyard, C. Chem. Commun. 1996, 333.
8. Kruppa, G. H.; Beauchamp, J. L. J. Am. Chem. Soc. 1986, 108, 2161.
9. Holmes, J. L.; Lossing, F. P.; Mayer, P. M. J. Am. Chem. Soc. 1991, 113, 9723.
10. Burgers, P. C.; Holmes, J. L. Org. Mass Spectrom. 1982, 17, 123.
11. Lias, S. G.; Bartmess, J. F.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
12. Benson, S. W. Chemical Kinetics, 2nd ed.; John Wiley and Sons Inc.: New York, 1976.
13. Holmes, J. L.; Mayer, P. M. J. Phys. Chem. 1995, 99, 1366.
14. Sunko, D. E.; Hirsl-Starcevic, S.; Pollack, S. K.; Hehre, W. J. J. Am. Chem. Soc. 1979, 101, 6163.
15. Danen, W. C.; Tipton, T. J.; Saunders, D. G. J. Am. Chem. Soc. 1971, 93, 5186.
16. Staley, R. H.; Wieting, R. D.; Beauchamp, J. L. J. Am. Chem. Soc. 1977, 99, 5964.
17. Houriet, R.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1979, 91, 1018.
18. Allison, J.; Ridge, D. P. J. Am. Chem. Soc. 1979, 101, 4998.
19. Sharma, R. B.; Sen Sharma, D. K.; Hiraoka, K.; Kebarle, P. J. Am. Chem. Soc. 1985, 107, 3747.
20. Dutler, R.; Rauk, A.; Sorensen, T. S.; Whitworth, S. M. J. Am. Chem. Soc. 1989, 111, 9024.
21. Dutler, R.; Rauk, A.; Whitworth, S. M.; Sorensen, T. S. J. Am. Chem. Soc. 1991, 113, 411.
22. Szulejko, J. E; McMahon, T. B. J. Am. Chem. Soc. 1993, 115, 7839.
23. Bauschlicher, C. W., Jr.; Partridge, H. J. Phys. Chem. 1994, 98, 1826. This value is also suggested in
24. (b) Traeger, J. C.; Kompe, B. M. Energetics of Organic Free Radicals, Search Series Volume 4; Blackie Academic & Professional: London, 1996; Chapter 3.
25. Zauer, O. A.; Takhistov, V. V. Zh. Org. Khim. 1986, 22, 672.
26. (a) Seetula, J. A.; Russell, J. J.; Gutman, D. J. Am. Chem. Soc. 1990, 112, 1347.
27. (b) Gutman, D. Acc. Chem. Res. 1990, 23, 375.
28. Walton, J. C. Chem. Soc. Rev. 1992, 21, 105.
29. (a) Ruchardt, C.; Herwig, K.; Eicher, S. Tetrahedron Lett. 1969, 421.
30. (b) Giese, B. Ibid. 1979, 857.
31. (c) Giese, B.; Stellmach, J. Chem. Ber. 1980, 113, 3294.
32. Lossing, F. P.; Holmes, J. L. J. Am. Chem. Soc. 1984, 106, 6917.
33. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
34. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
35. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
36. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
37. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
38. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
39. For examples see: (a) Greidanus, J. W. Can. J. Chem. 1971, 49, 3210. (b) Greene, R. L.; Kleschick, W. A.; Wahl, W. H., Jr. Tetrahedron Lett. 1971, 47, 4577. (c) Khullar, K. K.; Bell, C. L.; Bauer, L. J. Org. Chem. 1973, 38, 1042. (d) Polyakova, A. A.; Khramova, E. V.; Bagrii, Y. I.; Tsitsugina, N. N.; Lukashenko, I. M.; Frid, T. Y.; Sanin, P. I. Neftekhimiya, 1973, 13, 9. (e) Waltman, R. J.; Ling, A. C. Can. J. Chem. 1980, 58, 2189. (f) Schwarz, H.; Wesdemiotis, C.; Weiske, T.; Zeller, K.-P.; Muller, R. D. Z. Naturforsch. 1980, 35b, 207. (g) Yinon, J.; Bulusu, S. Org. Mass Spectrom. 1986, 21, 529.
40. Wesdemiotis, C.; Schilling, M.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1979, 18, 950.
41. Sieber, S.; Buzek, P. Schleyer, P.v.R.; Koch, W.; de M. Carneiro, J. W. J. Am. Chem. Soc. 1993, 115, 259.
42. Holmes, J. L.; McGillivray, D.; Isaacs, N. S. Org. Mass Spectrom. 1974, 9, 510 and references therein.