Structures of the C8H6+ Cation Formed upon Loss of Acetylene from Ionized Naphthalene

Journal of Physical Chemistry A

Volumn 103, Issue 21, 1999, Pages 4174-4181

  Schroeter, Katrin ^a   Schröder, Detlef ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000311859     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp990377v     Document Type: Article

References (80)

1. (a) Freudental, R. I., Jones, P. W., Eds. Polynuclear Aromatic Hydrocarbons; Raven Press: New York, 1976.
2. (b) Ahrens, J.; Keller, A.; Kovacs, R.; Homann, K.-H. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 1823, and references therein.
3. (a) De Frees, D. J.; Miller, M. D.; Talbi, D.; Pauzat, F.; Ellinger, Y. Astrophys. J. 1993, 408, 530.
4. (b) For criticism of this hypothesis, however, see: Schlemmer, S.; Cook, D. J.; Harrison, J. A.; Wurfel, B.; Chapman, W.; Saykally, R. J. Science 1994, 265, 1686.
5. Bohme, D. K. Chem. Rev. 1992, 92, 1487.
6. McLafferty, F. W.; Turecek, F. Interpretation of Mass Spectra; University Science Books: Mill Valley, 1993.
7. (a) Doretti, L.; Maccioni, A. M.; Traldi, P. Biomed. Environ. Mass Spectom. 1986, 13, 381.
8. (b) Ekern, S. P.; Marshall, A. G.; Szczepanski, J.; Vala, M. J. Phys. Chem. A 1998, 102, 3498.
9. Pachuta, S. J.; Kenttämaa, H. I.; Sack, T. M.; Cerny, R. L.; Tomer, K. B.; Ägross, M. L.; Pachuta, R. R.; Cooks, R. G. J. Am. Chem. Soc. 1988, 110, 657.
10. Rosenstock, H. M.; Dannacher, J.; Liebman, J. F. Radiat. Phys. Chem. 1982, 20, 7.
11. Kuck, D. Mass Spectrom. Rev. 1990, 9, 187.
12. Gotkis, Y.; Oleinikova, M.; Naor, M.; Lifshitz, C. J. Phys. Chem. 1993, 97, 12282.
13. (a) Jochims, H. W.; Rasekh, R.; Rühl, E.; Baumgärtel, H.; Leach, S. Chem. Phys. 1992, 168, 159.
14. (b) Jochims, H. W.; Rühl, E.; Baumgärtel, H.; Tobita, S.; Leach, S. Astrophys. J. 1994, 420, 307.
15. Ling, Y.; Martin, J. M. L.; Lifshitz, C. J. Phys. Chem. A 1997, 101, 219.
16. Ho, Y. P.; Dunbar, R. C.; Lifshitz, C. J. Am. Chem. Soc. 1995, 117, 6504.
17. (a) MacDonalds, C. G.; Shannon, J. S. Austral. J. Chem. 1962, 15, 771.
18. (b) Budzikiewicz, H.; Stolze, R. Monatsh. Chem. 1977, 108, 869.
19. (a) Schalley, C. A.; Fiedler, A.; Hornung, G.; Wesendrup, R.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1997, 3, 626.
20. (b) Schröder, D.; Schroeter, K.; Zummack, W.; Schwarz, H. J. Am. Soc. Mass Spectrom., in press.
21. For an experimental study of the cubene anion, see: Staneke, P. O.; Ingemann, S.; Eaton, P.; Nibbering, N. M. M.; Kass, S. R. J. Am. Chem. Soc. 1994, 116, 6445.
22. Theoretical studies have even dealt with elusive species such as bitetrahedryl, see for example: (a) Xie, Y.; Schaefer, H. F. Chem. Phys. Lett. 1989, 161, 516.
23. (b) Schleyer, P. v. R.; Bremer, M. Angew. Chem. 1989, 101, 1264; Angew. Chem., Int. Ed. Engl. 1989, 28, 1226.
24. (b) Schleyer, P. v. R.; Bremer, M. Angew. Chem. 1989, 101, 1264; Angew. Chem., Int. Ed. Engl. 1989, 28, 1226.
25. + isomers is enormous. A literature survey can be extracted from the QCLDB database at the Institute of Molecular Sciences, Okazaki, Japan, see: http://qcldb.ims.ac.jp/logine.html.
26. Schalley, C. A.; Schröder, D.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1996, 153, 173.
27. Busch, K. L.; Glish, G. L.; McLuckey, S. A. Mass Spectrometry/ Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry; VCH Publishers: Weinheim, Germany, 1988.
28. (a) Wesdemiotis, C.; McLafferty, F. W. Chem. Rev. 1987, 87, 485.
29. (b) McMahon, A. W.; Chowdhury, S. K.; Harrison, A. G. Org. Mass Spectrom. 1989, 24, 620.
30. (c) Schröder, D.; Schalley, C. A.; Goldberg, N.; Hrušák, J.; Schwarz, H. Chem. Eur. J. 1996, 2, 1235.
31. Schröder, D.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1995, 146/147, 183.
32. Bubb, W. A.; Sternhell, S. Aust. J. Chem. 1976, 29, 1685.
33. Haynes, L. J.; Heilbron, I.; Jones, E. H. R.; Sondheimer, F. J. Chem Soc. 1947, 1583.
34. Cook, L. L.; Jones, E. H. R.; Whiting, M. C. J. Chem. Soc. 1952, 2883.
35. Stolze, R.; Budzikiewicz, H. Monatsh. Chem. 1978, 109, 331.
36. Dyke, J. M.; Ozeki, H.; Takahashi, M.; Cockett, M. C. R.; Kimura, K. J. Chem. Phys. 1992, 97, 8926.
37. For a similar example, see: Depke, G.; Hanack, M.; Hümmer, W.; Schwarz, H. Angew. Chem. 1983, 95, 806; Angew. Chem., Int. Ed. Engl. 1983, 22, 786.
38. For a similar example, see: Depke, G.; Hanack, M.; Hümmer, W.; Schwarz, H. Angew. Chem. 1983, 95, 806; Angew. Chem., Int. Ed. Engl. 1983, 22, 786.
39. Vékey, K. J. Mass Spectrom. 1996, 31, 445.
40. Vékey, K. Mass Spectrom. Rev. 1995, 14, 195.
41. Even though the loss of acetylene from ionized azulene includes statistical (72%) as well as direct (28%) pathways, this difference is not manifested in the behavior of the long-lived ions sampled in the present experiments, see ref 25.
42. (a) Schalley, C. A.; Hornung, G.; Schrö;der, D.; Schwarz, H. Int. J. Mass Spectrom. 1998, 172, 181.
43. (b) Schröder, D.; Heinemann, C.; Schwarz, H.; Harvey, J. N.; Dua, S.; Blanskby, S. J.; Bowie, J. H. Chem. Eur. J. 1998, 4, 2550.
44. This statement does not hold true in general. Thus, some transients having rather low or even negative electron affinities have been observed by CR and NR experiments: (a) ref 20c and 31.
45. (b) Schröder, D.; Schalley, C. A.; Harvey, J. N.; Schwarz, H. Int. J. Mass Spectrom. 1999, 185/186/ 187, 25.
46. (a) Feng, R.; Wesdemiotis, C.; Zhang, M.-Y.; Marchetti, M.; McLafferty, F. W. J. Am. Chem. Soc. 1989, 111, 1986.
47. (b) Zhang, M.-Y.; Wesdemiotis, C.; Marchetti, M.; Danis, P. O.; Ray, J. C.; Carpenter, B. K.; McLafferty, F. W. J. Am. Chem. Soc. 1989, 111, 8341.
48. m, see: Van Orden, A.; Saykally, R. J. Chem. Rev. 1998, 98, 2313.
49. mH (m = 2, 4, 6), see: Natterer, J.; Koch, W. Mol. Phys. 1995, 84, 691.
50. 3H, see: Aoki, K.; Hashimoto, K.; Ikuta, S.; Nomura, O. Chem. Phys. Lett. 1995, 242, 527.
51. 5H, see: Dua, S.; Sheldon, J. C.; Bowie, J. H. J. Chem. Soc., Chem. Commun. 1995, 1067.
52. 7H, see: Woon, D. E. Chem. Phys. Lett. 1995, 244, 45.
53. 8H, see: Sobolewski, A. L.; Adamowicz, L. J. Chem. Phys. 1995, 102, 394.
54. Blanksby, S. J.; Dua, S.; Bowie, J. H.; Schröder, D.; Schwarz, H. J. Phys. Chem. A 1998, 102, 9949.
55. 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.
56. (a) Kato, S.; Lee, H. S.; Gareyev, R.; Wenthold, P. G.; Lineberger, W. C.; DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1997, 119, 7863.
57. (b) Kato, S.; Gareyev, R.; DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1998, 120, 5033.
58. (a) Schalley, C. A. Gas-Phase Ion Chemistry of Peroxides, Dissertation, Technische Universität Berlin D83; Shaker: Herzogenrath, Germany, 1997.
59. (b) Hornung, G.; Schalley, C. A.; Dieterle, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1997, 3, 1866.
60. (c) Schalley, C. A.; Hornung, G.; Schröder, D.; Schwarz, H. Chem. Soc. Rev. 1998, 27, 91.
61. (d) Schröder, D.; Harvey, J. N.; Aschi, M.; Schwarz, H. J. Chem. Phys. 1998, 108, 8446.
62. + cation.
63. Similarly, isotopic scrambling is reduced in NR spectra, see: Drinkwater, D. E.; McLafferty, F. W. Org. Mass Spectrom. 1993, 28, 378.
64. Wesdemiotis, C.; Feng, R.; Williams, E. R.; McLafferty, F. W. Org. Mass Spectrom. 1986, 21, 689.
65. fH° (4) values of 140, 135, and 145 kcal/mol, respectively, can be derived. Note that the corresponding reactions of the lower homologues predict the known heat of formation of 2,4-hexadiyne within ±5 kcal/mol.
66. Brogli, F.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E. Helv. Chim. Acta 1973, 56, 2171.
67. One option is the use of alkali metals as collision gases, see for example: Hayakawa, S.; Endoh, H.; Arakawa, K.; Morishita, N. Int. J. Mass Spectrom. Ion Processes 1997, 171, 209.
68. In ref 46, the all-trans isomer was considered; in the present context, however, stereochemical features are not included.
69. Köppel, C.; Schwarz, H.; Bohlmann, F. Org. Mass Spectrom. 1974, 9, 324.
70. fH°(13) = 97.8 kcal/mol for the neutral diendiyne was estimated based on increment rules.
71. fH°(13) = 97.8 kcal/mol (ref 46) is unexpectedly large. For example, the heats of formation of 2,4-hexadiyne and hexa-1,5-dien-3-yne differ by only 6 kcal/mol in favor of the latter (ref 36).
72. Bally, T. Chimia 1994, 48, 378.
73. For related effects in the ring-opening of phenyl radical, see: (a) Dewar, M. J. S.; Gardiner, W. C., Jr.; Frenklach, M.; Oref, I. J. Am. Chem. Soc. 1987, 109, 4456.
74. (b) Huang, J. H.; Han, K.-L.; Deng, W.-Q.; He, G.-Z. Chem. Phys. Lett. 1997, 273, 205.
75. + ion, see: (a) van der Hart, W. J. J. Am. Soc. Mass Spectrom. 1995, 6, 513.
76. (b) van der Hart, W. J. J. Am. Soc. Mass Spectrom. 1996, 7, 731.
77. (c) van der Hart, W. J. J. Am. Soc. Mass Spectrom. 1997, 8, 594.
78. (d) van der Hart, W. J. J. Am. Soc. Mass Spectrom. 1997, 8, 599.
79. (e) van der Hart, W. J. Int. J. Mass Spectrom. Ion Processes 1997, 171, 269.
80. (f) van der Hart, W. J. Int. J. Mass Spectrom. 1998, 176, 23.