Gas-phase syntheses of three isomeric C5H2 radical anions and their elusive neutrals. A joint experimental and theoretical study

Journal of Physical Chemistry A

Volumn 102, Issue 48, 1998, Pages 9949-9956

  Blanksby, Stephen J ^a   Dua, Suresh ^a   Bowle, John H ^a   Schröder, Detlef ^b   Schwarz, Helmut ^b  

^a UNIVERSITY OF ADELAIDE   (Australia)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000020755     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp982780s     Document Type: Article

References (83)

1. Thaddeus, P.; Vrtilek, J. M.; Gottlieb, C. A. Astrophys. J. 1985, 299, L63.
2. Thaddeus, P.; Gottlieb, C. A.; Mollaaghababa, R.; Vrtilek, J. M. J. Chem. Soc., Faraday Trans. 1993, 89, 2125.
3. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
4. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
5. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
6. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
7. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
8. For matrix trapping, see: (a) Skell, P. S.; Klebe, J. J. Am. Chem. Soc. 1960, 82, 247. (b) Reisenauer, H. P.; Maier, G.; Reimann, A.; Hoffmann, R. W. Angew. Chem. 1984, 96, 596. (c) Maier, G.; Reisenauer, H. P.; Schwab, W.; Carsky, P.; Hess, B. A.; Schaad, L. J. J. Am. Chem. Soc. 1987, 109, 5183. (d) Seburg, R. A.; McMahon, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2009. (e) Seburg, R. A.; DePinto, J. T.; Patterson, E. V.; McMahon, R. J. J Am. Chem. Soc. 1995, 117, 835. (f) Seburg, R. A.; Patterson, E. V.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 1997, 119, 5847.
9. For cations see: (a) Smith, D.; Adams, N. G. Int. J. Mass Spectrom. Ion Processes 1987, 76, 307. (b) Prodnuk, S. D.; DePuy, C. H.; Bierbaum, V. M. Int. J. Mass Spectrom. Ion Processes 1990, 100, 693. (c) Prodnuk, S. D.; Gronert, S.; Bierbaum, V. M.; DePuy, C. H. Org. Mass Spectrom. 1992, 27, 416. (d) Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99. (e) Chyall, L. J.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1995, 149/150, 257.
10. For cations see: (a) Smith, D.; Adams, N. G. Int. J. Mass Spectrom. Ion Processes 1987, 76, 307. (b) Prodnuk, S. D.; DePuy, C. H.; Bierbaum, V. M. Int. J. Mass Spectrom. Ion Processes 1990, 100, 693. (c) Prodnuk, S. D.; Gronert, S.; Bierbaum, V. M.; DePuy, C. H. Org. Mass Spectrom. 1992, 27, 416. (d) Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99. (e) Chyall, L. J.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1995, 149/150, 257.
11. For cations see: (a) Smith, D.; Adams, N. G. Int. J. Mass Spectrom. Ion Processes 1987, 76, 307. (b) Prodnuk, S. D.; DePuy, C. H.; Bierbaum, V. M. Int. J. Mass Spectrom. Ion Processes 1990, 100, 693. (c) Prodnuk, S. D.; Gronert, S.; Bierbaum, V. M.; DePuy, C. H. Org. Mass Spectrom. 1992, 27, 416. (d) Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99. (e) Chyall, L. J.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1995, 149/150, 257.
12. For cations see: (a) Smith, D.; Adams, N. G. Int. J. Mass Spectrom. Ion Processes 1987, 76, 307. (b) Prodnuk, S. D.; DePuy, C. H.; Bierbaum, V. M. Int. J. Mass Spectrom. Ion Processes 1990, 100, 693. (c) Prodnuk, S. D.; Gronert, S.; Bierbaum, V. M.; DePuy, C. H. Org. Mass Spectrom. 1992, 27, 416. (d) Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99. (e) Chyall, L. J.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1995, 149/150, 257.
13. For cations see: (a) Smith, D.; Adams, N. G. Int. J. Mass Spectrom. Ion Processes 1987, 76, 307. (b) Prodnuk, S. D.; DePuy, C. H.; Bierbaum, V. M. Int. J. Mass Spectrom. Ion Processes 1990, 100, 693. (c) Prodnuk, S. D.; Gronert, S.; Bierbaum, V. M.; DePuy, C. H. Org. Mass Spectrom. 1992, 27, 416. (d) Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99. (e) Chyall, L. J.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1995, 149/150, 257.
14. For anions, see: (a) Dawson, J. H. J.; Jennings, K. R. J. Chem. Soc., Faraday Trans. 2 1976, 72, 700. (b) Dawson, J. H. J.; Kaandorp, Th. A. M.; Nibbering, N. M. M. Org. Mass Spectrom. 1977, 12, 330. (c) Robinson, M. S.; Polak, M. L.; Bierbaum, V. M.; DePuy, C. H.; Lineberger, W. C. J. Am. Chem. Soc. 1995, 117, 6766.
15. For anions, see: (a) Dawson, J. H. J.; Jennings, K. R. J. Chem. Soc., Faraday Trans. 2 1976, 72, 700. (b) Dawson, J. H. J.; Kaandorp, Th. A. M.; Nibbering, N. M. M. Org. Mass Spectrom. 1977, 12, 330. (c) Robinson, M. S.; Polak, M. L.; Bierbaum, V. M.; DePuy, C. H.; Lineberger, W. C. J. Am. Chem. Soc. 1995, 117, 6766.
16. For anions, see: (a) Dawson, J. H. J.; Jennings, K. R. J. Chem. Soc., Faraday Trans. 2 1976, 72, 700. (b) Dawson, J. H. J.; Kaandorp, Th. A. M.; Nibbering, N. M. M. Org. Mass Spectrom. 1977, 12, 330. (c) Robinson, M. S.; Polak, M. L.; Bierbaum, V. M.; DePuy, C. H.; Lineberger, W. C. J. Am. Chem. Soc. 1995, 117, 6766.
17. For neutrals, see: (a) ref 3f. For ions, see: (b) Ikuta, S. J. Chem. Phys. 1997, 107, 4579 and references therein.
18. For neutrals, see: (a) ref 3f. For ions, see: (b) Ikuta, S. J. Chem. Phys. 1997, 107, 4579 and references therein.
19. (a) Natterer, J.; Koch, W.; Schröder, D.; Goldberg, N.; Schwarz H. Chem. Phys. Lett. 1994, 229, 429.
20. (b) Petrie, S. Mon. Not. R. Astron. Soc. 1996, 281, 137.
21. (c) Petrie, S.; Herbst, E. Astrophys. J. 1997, 491, 210.
22. Fulara, J.; Freivogel, P.; Forney, D.; Maier, J. P. J. Chem. Phys. 1995, 103, 8805.
23. McCarthy, M. C.; Travers, M. J.; Kovács, A.; Chen, W.; Novick, S. E.; Gottlieb, C. A.; Thaddeus, P. Science 1997, 275, 519.
24. (a) Cooper, D. L.; Murphy, S. C. Astrophys. J. 1988, 333, 482.
25. (b) Fan, Q.; Pfeiffer, G. V. Chem. Phys.Lett. 1989, 162, 472.
26. (c) Parent, D. C. J. Am. Chem. Soc. 1990, 112, 5966.
27. Seburg, R. A.; McMahon, R. J.; Stanton, J. F.; Gauss, J. J. Am. Chem. Soc. 1997, 119, 10838.
28. Sülzle, D.; Schwarz, H. Chem. Phys. Lett. 1989, 156, 397.
29. Goldberg, N.; Sülzle, D.; Schwarz, H. Chem. Phys. Lett. 1993, 213, 593.
30. (a) Bowie, J. H.; Blumenthal, T. J. Am. Chem. Soc. 1975, 97, 2959.
31. (b) Szulejko, J. E.; Bowie, J. H.; Howe, I.; Beynon, J. H. Int. J. Mass Spectrom. Ion Phys. 1980, 13, 76.
32. (c) Bursey, M. M. Mass Spectrom. Rev. 1990, 9, 555.
33. (a) Goldberg, N.; Schwarz, H. Acc. Chem. Res. 1994, 27, 347.
34. (b) Zagorevskii, D. V.; Holmes, J. L. Mass Spectrom. Rev. 1994, 13, 133.
35. Dua, S.; Sheldon, J. C.; Bowie, J. H. J. Chem. Soc., Chem. Commun. 1995, 1067.
36. Blanksby, S. J.; Dua, S.; Bowie, J. H.; Sheldon, J. C. Chem. Commun. 1997, 1833.
37. 2, see: (a) Oakes, J. M.; Ellison, G. B. Tetrahedron 1986, 42, 6263. (b) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C. J. Chem. Phys. 1996, 105, 10696. (c) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C.; Boldyrev, A. I.; Gutowski, M. J. Chem. Phys. 1996, 105, 10706.
38. 2, see: (a) Oakes, J. M.; Ellison, G. B. Tetrahedron 1986, 42, 6263. (b) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C. J. Chem. Phys. 1996, 105, 10696. (c) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C.; Boldyrev, A. I.; Gutowski, M. J. Chem. Phys. 1996, 105, 10706.
39. 2, see: (a) Oakes, J. M.; Ellison, G. B. Tetrahedron 1986, 42, 6263. (b) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C. J. Chem. Phys. 1996, 105, 10696. (c) Yokoyama, K.; Leach, G. W.; Kim, J. B.; Lineberger, W. C.; Boldyrev, A. I.; Gutowski, M. J. Chem. Phys. 1996, 105, 10706.
40. Stringer, M. B.; Bowie, J. H.; Holmes, J. L. J. Am. Chem. Soc. 1986, 108, 3888.
41. (a) Terlouw, J. K.; Burgers, P. C.; Holmes, J. L. Org. Mass Spectrom. 1979, 14, 307.
42. (b) Burgers, P. C.; Holmes, J. L.; Mommers, A. A.; Szulejko, J. E. J. Am. Chem. Soc. 1984, 106, 521.
43. DePuy, C. H.; Bierbaum, V. M.; Flippin, L. A.; Grabowski, J. J.; King, G. K.; Schmitt, R. J.; Sullivan, S. A. J. Am. Chem. Soc. 1980, 102, 5012.
44. Holmes, J. L. Org. Mass Spectrom. 1985, 20, 169.
45. (a) Hornung, G.; Schalley, C. A.; Dieterle, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1997, 3, 1866.
46. (b) Schalley, C. A.; Hornung, G.; Schröder, D.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1998, 172, 181.
47. (c) Schalley, C. A.; Hornung, G.; Schröder, D.; Schwarz, H. Chem. Soc. Rev. 1998, 27, 91.
48. Holmes, A. B.; Jennings-White, C. L. D.; Schulthess, A. H. J. Chem. Soc. , Chem. Commun. 1979, 840.
49. Polyacetylenes are known to be unstable (see: Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsvevier: Amsterdam, 1988) and potentially explosive, and hence further purification was not attempted unless absolutely necessary.
50. (a) Coles, B. F.; Walton, D. R. M. Synthesis 1975, 6, 390.
51. (b) Jones, G. E.; Holmes, A. B. Tetrahedron Lett. 1982, 23, 3203.
52. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsvevier: Amsterdam, 1988; Chapter IV.
53. (a) Jones, E. R. H.; Lee, H. H.; Whiting, M. C. J. Chem. Soc. 1956, 4765.
54. (b) Jones, E. R. H.; Skatteböl, L.; Whiting, M. C. J. Chem. Soc. 1960, 3483.
55. Hauptmann, H. Tetrahedron Lett. 1974, 40, 3587.
56. (a) Landini, D.; Montanari, F.; Rolla, F. Synthesis 1979, 134.
57. (b) Piancatelli, G.; Scettri, A.; D'auria, M. Synthesis 1982, 245.
58. (a) Becke, A. D. J. Phys. Chem. 1993, 98, 5648.
59. (b) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; 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.; Gonzales, C.; Pople, J. A.GAUSSIAN94, Revision B3; GAUSSIAN Inc.: Pittsburgh, PA, 1995.
61. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
62. (a) Cizek, J. Adv. Chem. Phys. 1969, 14, 35.
63. (b) Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem. 1978, XIV, 545.
64. (c) Hampel, C.; Peterson, K.; Werner, H.-J. Chem. Phys. Lett. 1992, 190, 1.
65. (d) Watts, J. D.; Gauss, J.; Bartlett, R. J. J. Chem. Phys. 1993, 98, 8718.
66. (e) Knowles, P. J.; Hampel, C.; Werner, H.-J. J. Chem. Phys. 1993, 99, 5219.
67. (f) Deegan, M. J. O.; Knowles, P. J. Chem. Phys. Lett. 1994, 227, 321.
68. (a) Dunning, Jr., T. H. J. Chem. Phys. 1989, 90, 1007.
69. (b) Woon, D. E.; Dunning, Jr., T. H. J. Chem. Phys. 1993, 98, 1358.
70. (c) Woon, D. E.; Dunning, Jr., T. H. J. Chem. Phys. 1993, 99, 3730.
71. MOLPRO 96.4; Werner, H.-J.; Knowles, P. J.; Almlöf, J.; Amos, R. D.; Deegan, M. J. O.; Elbert, S. T.; Hampel, C.; Meyer, W.; Peterson, K.; Pitzer, R.; Stone, A. J.; Taylor, P. R.; Lindh, R.
72. Dua, S.; Bowie, J. H.; Sheldon, J. C. J. Chem. Soc., Perkin Trans. 2 1994, 543.
73. 2O.
74. •-.
75. •- in the spectrum.
76. •-, which may make a small contribution to the m/z 64 parent ion.
77. A reviewer has suggested that isotopic scrambling may occur during the chemical ionization process itself. While this possibility cannot be excluded, the spectral data presented indicates that, if occurring at all, scrambling is incomplete and probably a minor process.
78. Lorquet, J. C.; Leyh-Nihaut, B.; McLafferty, F. W. Int. J. Mass Spectrom. Ion Processes 1990, 100, 465.
79. -1 less stable than the species shown (B3LYP/6-311+G*//B3LYP/6-31G level).
80. 11
81. •. This may explain why the hydroxyl function in these systems undergoes such facile carbon-oxygen bond homolysis (see Schemes 1 and 2).
82. Schulz, P. A.; Mead, R. D.; Jones, P. L.; Lineberger, W. C. J. Chem. Phys. 1982, 77, 1153.
83. •- are available as Supporting Information.