Transient hydrogen atom adducts to disulfides. Formation and energetics

Journal of the American Chemical Society

Volumn 122, Issue 10, 2000, Pages 2361-2370

  Tureček, František ^a   Polášek, Miroslav ^a   Frank, Aaron J ^a   Sadílek, Martin ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; DISULFIDE; HYDROGEN;

ARTICLE; DISULFIDE BOND; ELECTRON TRANSPORT; ENERGY TRANSFER; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0038079857     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993789q     Document Type: Article

References (91)

1. For a review, see: Atkinson, R. Gas-phase tropospheric chemistry of organic compounds; Journal of Physical and Chemical Reference Data, Monograph 2; American Institute of Physics: Woodbury, NY, 1994.
2. (a) Perkins, C. W.; Martin, J. C.; Arduengo, A. J.; Lau, W.; Alegria, A.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 7753.
3. (b) Smart, B. A.; Schiesser, C. H. J. Comput. Chem. 1995, 16, 1055. For a review, see:
4. (c) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265.
5. Gedye, R. N.; Sadana, Y. N. J. Org. Chem. 1980, 45, 3721.
6. Kariv-Miller, E.; Nanjudiah, C.; Eaton, J.; Swenson, K. E. J. Electroanal. Chem. 1984, 167, 141.
7. Bates, D. R. In Dissociative Recombination; Rowe, B. R., Mitchell, J. B. A., Canosa, A., Eds; NATO ASI Series; Plenum: New York, 1993; pp 1-10.
8. Adams, N. G. In Dissociative Recombination; Rowe, B. R., Mitchell, J. B. A., Canosa, A., Eds; NATO ASI Series; Plenum: New York, 1993; pp 99-112.
9. Zubarev, R. A.; Kelleher, N. L.; McLafferty, F. W. J. Am. Chem. Soc. 1998, 120, 3265.
10. Zubarev, R. A.; Kruger, N. A.; Fridriksson, E. K.; Lewis, M. A.; Horn, D. M.; Carpenter, B. K.; McLafferty, F. W. J. Am. Chem. Soc. 1999, 121, 2857.
11. Shaffer, S. A.; Sadilek, M.; Turecek, F.; Hop, C. E. C. A. Int. J. Mass Spectrom. Ion Processes 1997, 160, 137.
12. Shaffer, S. A.; Wolken, J. K.; Turecek, F. J. Am. Soc. Mass Spectrom. 1997, 8, 1111.
13. Sadilek, M.; Turecek, F. Int. J. Mass Spectrom. 1999, 185/186/ 187, 639.
14. Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 15027.
15. Stirk, K. M.; Kiminkinen, L. K. M.; Kenttamaa, H. I. Chem. Rev. 1992, 92, 1649.
16. (a) Nguyen, V. Q.; Turecek, F. J. Am. Chem. Soc. 1997, 119, 2280.
17. (b) Nguyen, V. Q.; Turecek, F. J. Mass Spectrom. 1997, 32, 55.
18. For reviews, see: (a) Wesdemiotis, C.; McLafferty, F. W. Chem. Rev. 1987, 87, 485.
19. (b) Terlouw, J. K.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 805.
20. (c) Holmes, J. L. Mass Spectrom. Rev. 1989, 8, 513.
21. (d) Terlouw, J. K. Adv. Mass Spectrom. 1989. 11, 984.
22. (e) McLafferty, F. W. Science 1990, 247, 925.
23. (f) Turecek, F. Org. Mass Spectrom. 1992, 27, 1087.
24. (g) Goldberg, N.; Schwarz, H. Acc. Chem. Res. 1994, 27, 347.
25. (h) Schalley, C. A.; Hornung, G.; Schroder, D.; Schwarz, H. Chem. Soc. Rev. 1998, 27, 91.
26. Turecek, F. J. Mass Spectrom. 1998, 33, 779.
27. (a) Wiliams, B. W.; Porter, R. F. J. Chem. Phys. 1980, 73, 5598.
28. (b) Jeon, S.-J.; Raksit, A. B.; Gellene, G. I.; Porter, R. F. J. Am. Chem. Soc. 1985, 107, 4129.
29. (c) Wesdemiotis, C.; Feng, R.; McLafferty, F. W. J. Am. Chem. Soc. 1986, 108, 5656.
30. (d) Raksit, A. B.; Porter, R. F. J. Chem. Soc., Chem. Commun. 1987, 500.
31. (e) Selgren, S. F.; Gellene, G. I. J. Phys. Chem. 1987, 87, 5804.
32. (f) Holmes, J. L.; Sirois, M. Org. Mass Spectrom. 1990, 25, 481.
33. (g) Wesdemiotis, C.; Fura, A.; McLafferty, F. W. J. Am. Soc. Mass Spectrom. 1991, 2, 459.
34. (h) Gu, M.; Turecek, F. J. Am. Chem. Soc. 1992, 114, 7146.
35. Sirois, M.; George, M.; Holmes, J. L. Org. Mass Spectrom. 1994, 29, 11.
36. (j) Shaffer, S. A.; Turecek, F. J. Am. Chem. Soc. 1994, 116, 8647.
37. (k) Shaffer, S. A.; Turecek, F. J. Am. Soc. Mass Spectrom. 1995, 6, 1004.
38. Shaffer, S. A.; Sadílek, M.; Turecek, F. J. Org. Chem. 1996, 61, 5234.
39. Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 9610.
40. (n) Nguyen, V. Q.; Sadilek, M.; Frank, A. J.; Ferrier, J. G.; Turecek, F. J. Phys. Chem. A 1997, 101, 3789.
41. (o) Wolken, J. K.; Nguyen, V. Q.; Turecek, F. J. Mass Spectrom. 1997, 32, 1162.
42. (p) Froøsig, L.; Turecek, F. J. Am. Soc. Mass Spectrom. 1998, 9, 242.
43. (a) Beagley, B.; McAloon, K. T. Trans. Faraday Soc. 1971, 67, 3216.
44. (b) Yokozeki, A.; Bauer, S. H. J. Phys. Chem. 1974, 80, 618.
45. (c) Kuhler, M.; Charpentier, L.; Sutter, D.; Dreizler, H. Z. Naturforsch., A: Phys., Phys. Chem., Kosmophys. 1974, 29A, 1335.
46. Turecek, F.; Gu, M.; Shaffer, S. A. J. Am. Soc. Mass Spectrom. 1992, 3, 493.
47. Vairamani, M.; Mirza, U. A.; Srinivas, R. Mass Spectrom. Rev. 1990, 9, 235.
48. (a) Danis, P.; Feng, R.; McLafferty, F. W. Anal. Chem. 1986, 58, 348.
49. (b) Turecek, F.; Drinkwater, D. E.; Maquestiau, A.; McLafferty, F. W. Org. Mass Spectrom. 1989, 24, 669.
50. (c) Shaffer, S. A.; Turecek, F.; Cerny, R. L. J. Am. Chem. Soc. 1993, 115, 12117.
51. Field, L.; Barbee, R. B. J. Org. Chem. 1969, 34, 36.
52. NIST/EPA/NIH Mass Spectral Library; http://webbook.nist.gov/ chemistry.
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz. J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Kumaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
54. (a) Becke, A. D. J. Chem. Phys 1993, 98, 1372, 5648.
55. (b) Stephens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
56. Möller, C.; Plesset, M. S. Phys. Rev. 1934, 45, 618.
57. (a) Mayer, I. Adv. Quantum Chem. 1980, 12, 189.
58. (b) Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530.
59. For the various frequency correction factors see, for example: (a) Rauhut, G.; Pulay, R. J. Phys. Chem. 1995, 99, 3093.
60. (b) Finley, J. W.; Stephens, P. J. J. Mol. Struct. (THEOCHEM) 1995, 227, 357.
61. (c) Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
62. (d) Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
63. (a) Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293.
64. (b) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
65. (c) Rughavachari, K.; Stefanov, B. B.; Curtiss, L. A. J. Chem. Phys. 1997, 106, 6764.
66. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
67. (b) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358.
68. (a) Turecek, F. J. Phys. Chem. A 1998, 102, 4703.
69. (b) Turecek, F.; Wolken, J. K. J. Phys. Chem. A 1999, 103, 1905.
70. (c) Wolken, J. K.; Turecek, F. J. Phys. Chem. A, 1999, 103, 6268.
71. (d) Wolken, J. K.; Turecek, F. J. Am. Chem. Soc. 1999, 121, 6010.
72. Levine, I. N. Physical Chemistry, 3rd ed.; McGraw-Hill: New York, 1988; p 839.
73. Mallard, W. G., Lindstrom, P. J., Eds. NIST Chemistry Webbook, NIST Standard Reference Database; National Institute of Science and Technology: Gaithersburg, MD, 1998; Vol. 69, http://webbook.nist.gov/ chemistry.
74. For a comprehensive review, see: (a) Deslongchamps, P. Stereo-electronic Effects in Organic Chemistry; Pergamon: Oxford, 1983.
75. For a discussion of stereoelectronic effects in gas-phase ion reactions, see: (a) Turecek, F.; Hanus, V. Advances in Mass Spectrometry, 1985; Todd, J. F. J., Ed.; Wiley: New York, 1986; pp 215-224.
76. (b) Turecek, F. Int. J. Mass Spectrom. Ion Processes 1991, 108, 137.
77. Sumathi, R.; Peyerimhoff, S. D.; Sengupta, D. J. Phys. Chem. A 1999, 103, 772.
78. Uncorrected for basis set superposition error.
79. 875 for the equilibrium of 2H, anti-5, syn-5, anti-6, and syn-6.
80. (a) Nguyen, V. Q.; Shaffer, S. A.; Turecek, F.; Hop, C. E. C. A. J. Phys. Chem. 1995, 99, 15454.
81. (b) Frank, A. J.; Turecek, F. J. Phys. Chem. A 1999, 103, 5348.
82. (c) Polasek, M.; Turecek, F. J. Phys. Chem. A 1999, 103, 9241.
83. Calculated according to the published method: Dunbar, R. C. J. Chem. Phys. 1989, 90, 7369.
84. Lifshitz, C. Mass Spectrom. Rev. 1982, 1, 309.
85. -1, ref 42).
86. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
87. -1, ref 47).
88. Chase, M. W., Jr. NIST-JANAF Themochemical Tables, 4th ed.; Journal of Physical and Chemical Reference Data, Monograph 9; American Institute of Physics: Woodbury, NY, 1998; pp 1-1951.
89. Tsang, W. In Energetics of Organic Free Radicals; Martinho Simoes, J. A., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional: London, 1996; pp 22-58.
90. Hawari, J. A.; Griller, D.; Lossing, F. P. J. Am. Chem. Soc. 1986, 108, 3273.
91. Traeger, J. C.; McLoughlin, R. G. J. Am. Chem. Soc. 1981, 103, 3647.