Ultraviolet photoelectron spectroscopy of the o-, m-, and p-benzyne negative ions. Electron affinities and singlet-triplet splittings for o-, m- , and p-benzyne

Journal of the American Chemical Society

Volumn 120, Issue 21, 1998, Pages 5279-5290

  Wenthold, Paul G ^c   Squires, Robert R ^b   Lineberger, W C ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b PURDUE UNIVERSITY   (United States)

^c TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BENZYNE; FLUORINE; ION; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; ELECTRON; ENERGY; PREDICTION; SPECTROSCOPY; VIBRATION;

EID: 0032479044     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9803355     Document Type: Article

References (72)

1. Hoffman, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
2. Dreher, E.; Otto, R. Leibigs Ann. Chem. 1870, 154, 93.
3. Wittig, G. Narurwiss 1942, 30, 696.
4. Roberts, J. D.; Simmons, H. E.; Carlsmith, L. A.; Vaughan, C. W. J. Am. Chem. Soc. 1953, 75, 3290.
5. Kauffman, T.; Wirthwein, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 20.
6. Bryce, M. R.; Vernon, J. M. Adv. Heterocycl. Chem. 1981, 28, 183.
7. Bennett, M. A.; Schwemlein, H. P. Angew. Chem., Int. Ed. Engl. 1989, 28, 1296.
8. Berry, R. S.; Clardy, J., Schafer, M. E. Tetrahedron Lett. 1965, 6, 1003.
9. Berry, R. S.; Clardy, J.; Schafer, M. E. Tetrahedron Lett. 1965, 6, 1011.
10. Fischer, I. P.; Lossing, F. P. J. Am. Chem. Soc. 1963, 85, 1018.
11. Washburn, W. N.; Zahler, R.; Chen, I. J. Am. Chem. Soc. 1978, 100, 5863.
12. Billups, W. E.; Buynak, J. D.; Butler, D. J. Org. Chem. 1979, 44, 4218.
13. Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660.
14. Bergman, R. G. Acc. Chem. Res. 1973, 6, 25.
15. Enediyne Antibiotics as Antitumor Agents; Borders, D.; Doyle, T. W., Eds.; Marcel Dekker: New York, 1995.
16. Zein, N.; Sinha, A. M.; McGahren, W. J.; Ellestad, G. A. Science 1988, 240, 1198.
17. Nicolau, K. C.; Dai, W.-M. Angew. Chem., Int. Ed., Engl. 1991, 30, 1387.
18. Nicolau, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497.
19. Rosenstock, H. M.; Stockbauer, R.; Parr, A. C. J. Chim. Phys. 1980, 77, 745.
20. Pollack, S. K.; Hehre, W. J. Tetrahedron Lett. 1980, 21, 2483.
21. Maccoll, A.; Mathur, D. Org. Mass Spectrom. 1981, 16, 261.
22. Moini, M.; Leroi, G. E. J. Phys. Chem. 1986, 90, 4002.
23. Riveros, J. M.; Ingemann, S.; Nibbering, N. M. M. J. Am. Chem. Soc. 1991, 113, 1053.
24. Guo, Y.; Grabowski, J. J. J. Am. Chem. Soc. 1991, 113, 5923.
25. Wenthold, P. G.; Squires, R. R. J. Am. Chem. Soc. 1994, 116, 6401.
26. Matimba, H. E. K.; Crabbendam, A. M.; Ingemann, S.; Nibbering, N. M. M. J. Chem. Soc., Chem. Commun. 1991, 644.
27. Zhang, X.; Chen, P. J. Am. Chem. Soc. 1992, 114, 3147.
28. Wenthold, P. G.; Hu, J.; Squires, R. R. J. Am. Chem. Soc. 1996, 118, 11865.
29. Gronert, S.; DePuy, C. H. J. Am. Chem. Soc. 1989, 111, 9253.
30. Chapman, O. L.; Mattes, K.; McIntosh, C. L.; Pecansky, J.; Calder, G. V.; Orr, G. J. Am. Chem. Soc. 1973, 95, 6134.
31. Chapman, O. L.; Chang, C.-C.; Kolc, J.; Rosenquist, N. R.; Tomioka, H. J. Am. Chem. Soc. 1975, 97, 6586.
32. Dunkin, I. R.; MacDonald, J. G. J. Chem. Soc., Chem. Commun. 1979, 772.
33. Nam, H.-H.; Leroi, G. E. J. Mol. Struct. 1987, 157, 301.
34. Wentrup, C.; Blanch, R.; Briehl, H.; Gross, G. J. Am. Chem. Soc. 1988, 110, 1874.
35. Radziszewski, J. G.; Hess, B. A., Jr.; Zahradnik, R. J. Am. Chem. Soc. 1992, 114, 52.
36. Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347.
37. Marquardt, R.; Sander, W.; Kraka, E. Angew. Chem. Int. Engl. 1996, 35, 746.
38. Marquardt, R.; Balster, A.; Sander, W.; Kraka, E.; Cremer, D.; Ratzizewski, J. G. Angew. Chem. Int. Ed. Engl. 1998, 37, 955.
39. A listing of theoretical studies of the benzynes is given by Nash and Squires: Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1996, 118, 11872.
40. Cramer, C. J.; Nash, J. J.; Squires, R. R. Chem. Phys. Lett. 1997, 277, 311.
41. Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091.
42. Hoffman, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499.
43. Hoffman, R. Acc. Chem. Res. 1971, 4, 1.
44. Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113.
45. Schottelius, M. J.; Chen, P. J. Am. Chem. Soc 1996, 118, 4896.
46. Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958.
47. Ervin, K. M.; Lineberger, W. C. In Advances in Gas-Phase Ion Chemistry; Adams, N. G., Babcock, L. M., Eds.; JAI Press: Greenwich, 1992; Vol. 1; p 121.
48. Leopold, D. G.; Stevens-Miller, A. E.; Lineberger, W. C. J. Am. Chem. Soc. 1986, 108, 1379.
49. Bruins, A. P.; Ferrer-Correia, A. J.; Harrison, A. G.; Jennings, K. R.; Mitchum, R. K. Adv. Mass. Spectrom. 1978, 7, 355.
50. Wenthold, P. G.; Hu, J.; Squires, R. R. J. Am. Chem. Soc. 1994, 116, 6961.
51. Wenthold, P. G.; Hu, J.; Squires, R. R. J. Mass Spectrom. 1998, in press.
52. Neumark, D. M.; Lykke, K. R.; Andersen, T.; Lineberger, W. C. Phys. Rev. A 1985, 32, 1890.
53. Moore, C. E. Atomic Energy Levels; US GPO Circular No. 467: Washington, 1952.
54. Long, M. A.; Garnett, J. L.; Vining, R. F. W. J. Chem. Soc., Perkin Trans. 2 1975, 1298.
55. Gilles, M. K.; Ervin, K. M.; Ho, J.; Lineberger, W. C. J. Phys. Chem. 1992, 96, 1130.
56. Chen, P. In Unimolecular and Bimolecular Reaction Dynamics; Ng, C. Y., Baer, T., Powis, I., Eds.; John Wiley & Sons: New York, 1994.
57. Kohn, D. W.; Roberts, E. S. J.; Logan, C. F.; Chen, P. J. Phys. Chem. 1993, 97, 4936.
58. Wenthold, P. G.; Polak, M. L.; Lineberger, W. C. J. Phys. Chem. 1996, 100, 6920.
59. Gaussian 94; Frisch, M. J.; Trucks, G. W.; Schiegal, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Kieth, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, 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.; J. Baker; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc.: Pittsburgh, PA, 1994.
60. Lee, J.; Grabowski, J. J. Chem. Rev. 1992, 92, 1611.
61. Gunion, R. F.; Gilles, M. K.; Polak, M. L.; Lineberger, W. C. Int. J. Mass Spectrom. Ion Processes 1992, 117, 601.
62. Bevington, P. R. Data Reduction and Error Analysis for the Physical Sciences; McGraw-Hill: New York, 1969.
63. Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951.
64. Wilson, E. B., Jr. Phys. Rev. 1934, 45, 706.
65. Kraka, E.; Cremer, D.; Bucher, G.; Wandel, H.; Sander, W. Chem. Phys. Lett. 1991, 268, 313.
66. Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929.
67. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
68. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
69. Raghavachari, K.; Stefanov, B. B.; Curtiss, L. A. J. Chem. Phys. 1997, 106, 6764.
70. Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765.
71. Clauberg, H.; Minsek, D. W.; Chen, P. J. Am. Chem. Soc. 1992, 114, 99.
72. The small temperature correction has been neglected.