Methylsulfonyl and Methoxysulfinyl Radicals and Cations in the Gas Phase. A Variable-Time and Photoexcitation Neutralization-Reionization Mass Spectrometric and ab Initio/RRKM Study

Journal of Physical Chemistry A

Volumn 103, Issue 27, 1999, Pages 5348-5361

  Frank, Aaron J ^a   Turecek, Frantisek ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000010733     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp990946z     Document Type: Article

References (117)

1. Wayne, R.P. Chemistry of Atmospheres; Oxford: New York, 1993; Chapter 1.
2. Cullis, C. F.; Hirschler, M. M. Atmospheric Environment 1980, 14, 1263.
3. Tyndall, G. S.; Ravishankara, A. R. Int. J. Chem. Kinet. 1991, 23, 483.
4. Charlson, R. J.; Lovelock, J. E. Nature 1987, 326, 655.
5. Trindle, C.; Romberg, K. J. Phys. Chem. A 1998, 102, 270-273.
6. Laakso, D.; Smith, C. E.; Goumri, A.; Rocha, J.-D. R.; Marshall, P. Chem. Phys. Lett. 1994, 227, 377.
7. Davis, S. R. J. Phys. Chem. 1993, 97, 7535.
8. McKee, M. L. Chem. Phys. Lett. 1993, 211, 643.
9. Boyd, R. J.; Gupta, A.; Langler, R. F.; Lownie, S. P.; Pincock, J. A. Can. J. Chem. 1980, 58, 331.
10. Gozdz, A. S. Macromolecules 1990, 23, 910.
11. Culshaw, P. N.; Walton, J. C. Tetrahedron Lett. 1990, 31, 2457.
12. Swarts, S. G.; Becker, D.; DeBolt, S.; Sevilla, M. D. J. Phys. Chem. 1989, 93, 155.
13. Bennett, J. E.; Brunton, G.; Silben, B. C.; Whittall, P. E. J. Chem. Soc., Perkin Trans. 2 1988, 1359.
14. Chatgilialoglu, C.; Griller, D.; Guerra, M. J. Phys. Chem. 1987, 91, 3747.
15. Chatgilialoglu, C.; Gilbert, B. C.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1980, 10, 1429.
16. Gilbert, B. C.; Kirk, C. M.; Norman, R. O. C. J. Chem. Res., Synop. 1977, 173.
17. Andersen, R. S. J. Chem. Phys. 1977, 66, 5610.
18. Eriksen, T. E.; Lind, J. Radiochem. Radioanal. Lett. 1976, 25, 11.
19. Eriksen, T. E.; Lind, J.; Gillbro, T. Int. J. Radiat. Phys. 1976, 8, 655.
20. Gilbert, B. C.; Norman, R. O. C.; Sealy, R. C. J. Chem. Soc., Perkin Trans. 2 1975, 3, 1975.
21. Flockhart, B. D.; Ivin, K. J.; Pink, R. C.; Sharma, B. D. J. Chem. Soc. D 1971, 7, 339.
22. Good, A.; Thynne, J. C. J. Chem. Soc., Faraday Trans. 1 1967, 63, 2708.
23. James, F. C.; Kerr, J. A.; Simons, J. P. J. Chem. Soc., Faraday Trans, 1 1973, 63, 2124.
24. Turnipseed, A. A.; Barone, S. B.; Ravishankara, A. R. J. Phys. Chem. 1993, 97, 5926.
25. Domine, F.; Ravishankara, A. R.; Howard, C. J. J. Phys. Chem. 1992, 96, 2171.
26. Turnipseed, A. A.; Barone, S. B.; Ravishankara, A. R. J. Phys. Chem. 1992, 96, 7502.
27. Domine, F.; Murrells, T. P.; Howard, C. J. J. Phys. Chem. 1990, 94, 5839.
28. Tyndall, G. S.; Ravishankara, A. R. J. Phys. Chem. 1989, 93, 2426.
29. Moraes, L. A. B.; Eberlin, M. N. J. Chem. Soc., Perkin Trans. 2 1997, 2105.
30. Gozzo, F. C.; Sorrilha, A. E. P. M.; Eberlin, M. N. J. Chem. Soc., Perkin Trans. 2 1996, 587.
31. de Petris, G.; Fornarini, S.; Occhiucci, G. Int. J. Mass Spectrosc. Ion Proc. 1992, 112, 231.
32. Chatgilialoglu, C.; Guerra, M.; Pelli, B.; Traldi, P. Org. Mass Spectrosc. 1989, 24, 455.
33. For reviews see: (a) Wesdemiotis, C.; McLafferty, F. W. Chem. Rev. 1987, 87, 485.
34. (b) Terlouw, J. K.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 805.
35. (c) Holmes, J. L. Mass Spectrom. Rev. 1989, 8, 513.
36. (d) Terlouw, J. K. Adv. Mass Spectrom. 1989, 11, 984.
37. (e) McLafferty, F. W. Science, 1990, 247, 925.
38. (f) Turecek, F. Org. Mass Spectrom. 1992, 27, 1087.
39. (g) Goldberg, N.; Schwarz, H. Acc. Chem. Res. 1994, 27, 347.
40. (h) Schalley, C. A.; Hornung, G.; Schroder, D.; Schwarz, H. Chem. Soc. Rev. 1998, 27, 91.
41. Iraqi, M.; Goldberg, N.; Schwarz, H. J. Phys. Chem. 1994, 98, 2015-2017.
42. Turecek, F.; Drinkwater, D. E.; McLafferty, F. W. J. Am. Chem. Soc. 1989, 111, 7696-7701.
43. Egsgaard, H.; Carlsen, L.; Florencio, H.; Drewello, T.; Schwarz, H. Chem. Phys. Lett. 1988, 148, 537-540.
44. Sulzle, D.; Verhoeven, M.; Terlouw, J. K.; Schwarz, H. Angew. Chem., Int. 1988, 100, 1591-1592.
45. Turecek, F.; McLafferty, F. W.; Smith, B. J.; Radom, L. Int. J. Mass Spectrom. Ion Processes 1990, 101, 283-300.
46. Gu, M.; Turecek, F. J. Am. Chem. Soc. 1992, 114, 7146-7151.
47. (a) Frank, A. J.; Sadilek, M.; Ferrier, J. G.; Turecek, F. J. Am. Chem. Soc. 1996, 118, 11321-11322.
48. (b) Frank, A. J.; Sadilek, M.; Ferrier, J. G.; Turecek, F. J. Am. Chem. Soc. 1997, 119, 12343-12353.
49. Schmidt, H.; Steudel, R.; Sulzle, D.; Schwarz, H. Inorg. Chem. 1992, 31, 941.
50. Iraqi, M.; Schwarz, H. Chem. Phys. Lett. 1994, 221, 359.
51. Flammang, R.; Wentrup, C. Sulfur Rep. 1997, 20, 255-278.
52. (a) Kuhns, D. W.; Tran, T. B.; Shaffer, S. A.; Turecek, F. J. Phys. Chem. 1994, 98, 4845-4853.
53. (b) Kuhns, D. W.; Turecek, F. Org. Mass Spectrom. 1994, 29, 463-469.
54. (c) Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 224-232.
55. (a) Sadilek, M.; Turecek, F. J. Phys. Chem. 1996, 100, 9610-9614.
56. (b) Sadilek, M.; Turecek, F. Chem. Phys. Lett. 1996, 263, 203-208.
57. Nguyen, V. Q.; Sadilek, M.; Frank, A. J.; Ferrier, J. G.; Turecek, F. J. Phys. Chem. A 1997, 101, 3789-3799.
58. (a) Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell: London, 1990.
59. (b) Baer, T.; Hase, W. L. Unimolecular Reaction Dynamics. Theory and Experiment; Oxford: New York, 1996.
60. (c) Hase, W. L. Acc. Chem. Res. 1998, 31, 659-665.
61. Turecek, F.; Gu, M.; Shaffer, S. A. J. Am. Soc. Mass Spectrom. 1992, 3, 493.
62. Fitch, W. L.; Sauter, A. D. Anal. Chem. 1983, 55, 832.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, 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.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
64. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372, 5648.
65. (b) Stephens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
66. Hehre, W. J.; Radom, L.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 82-88.
67. See for example: (a) Bauschlicher, C. W.; Partridge, H. J. Chem. Phys. 1995, 103, 1788.
68. (b) Turecek, F. J. Phys. Chem. A, 1998, 102, 4703-4713.
69. (a) Xantheas, S. S.; Dunning, T. H., Jr. J. Phys. Chem. 1993, 97, 6616.
70. (b) McKee, M. L. J. Phys. Chem. 1993, 97, 10971-10976.
71. Smart, B. A.; Schiesser, C. H. J. Comput. Chem. 1995, 16, 1055.
72. Ruttink, P. J. A.; Burgers, P. C.; Francis, J. T.; Terlouw, J. K, J. Phys. Chem. 1996, 100, 9694.
73. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
74. Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4534.
75. (a) Rauhut, G.; Pulay, R. J. Phys. Chem. 1995, 99, 3093.
76. (b) Finley, J. W.; Stephens, P. J. J. Mol. Struct. (THEOCHEM) 1995, 357, 225.
77. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
78. For different scaling factors see: (d) Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
79. (a) Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293.
80. (b) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
81. Raghavachari, K.; Stefanov, B. B.; Curtiss, L. A. J. Chem. Phys. 1997, 106, 6764.
82. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
83. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149.
84. Zhu, L.; Hase, W. L. Quantum Chemistry Program Exchange; Indiana University: Bloomington, IN, 1994; Program No. QCPE 644.
85. Zhu, L.; Hase, W. L. Chem. Phys. Lett. 1990, 175, 117-123.
86. (a) Munson, M. S. B.; Franklin, J. L. J. Phys. Chem. 1964, 6, 8, 3191.
87. (b) Bowen, R. D.; Williams, D. H. J. Chem. Soc., Chem. Commun. 1977, 378.
88. (c) Schleyer, P. v. R.; Jemmis, A. D.; Pople, J. A. J. Chem. Soc., Chem. Commun. 1978, 190.
89. (d) Bursey, M. M.; Hass, J. R.; Harvan, D. J.; Parker, C. E. J. Am. Chem. Soc. 1979, 101, 5485.
90. (e) Burgers, P. C.; Holmes, J. L. Org. Mass Spectrom. 1984, 19, 452.
91. (f) Yarkony, D. R.; J. Am. Chem. Soc. 1992, 114, 5406.
92. (g) Kuo, S.-C; Zhang, Z.; Klemm, R. B.; Liebman, J. F.; Stief, L. I.; Nesbitt, F. L. J. Phys. Chem. 1994, 98, 4026.
93. (h) Aschi, M.; Harvey, J. N.; Schalley, C. A.; Schroder, D.; Schwarz, H. J. Chem. Soc., Chem. Commun. 1998, 531.
94. (a) Carpenter, B. K. J. Am. Chem. Soc. 1983, 105, 1700-1701.
95. (b) Dewar, M. J. S.; Merz, K. M., Jr. J. Am. Chem. Soc. 1986, 108, 5634-5635.
96. Mallard, W. G.; Linstrom, P. J., Eds. NIST Chemistry Webbook, NIST Standard Reference Database, No. 69, March 1998. National Institute of Standards and Technology: Gaithersburg, MD. http//webbook.nist.gov/ chemistry.
97. f,298 and do not include uncertainties in the experimental standard heats of formation.
98. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of He(I) Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Societies Press: Tokyo, 1981; p 23.
99. (a) Nguyen, M. T.; Creve, S.; Vanquickenborne, L. G. J. Phys. Chem. 1996, 100, 18422-18425.
100. (b) Turecek, F. J. Mass Spectrom. 1998, 33, 779-795.
101. McKee, M. L. J. Am. Chem. Soc. 1998, 120, 3963-3969.
102. Turecek, F.; Wolken, J. K. J. Phys. Chem. A 1999, 103, 1905.
103. Amaudrut, J.; Pasto, D. J.; Wiest, O. J. Org. Chem. 1998, 63, 6061.
104. Hase, W. L.; Wardlaw, D. M. In Advances in Gas-Phase Photochemistry and Kinetics, Ashfold, M. N. R. Baggott, J. E., Eds.; Royal Society of Chemistry: London, 1989; Chapter 4, pp 171-208.
105. (a) Laidler, K. J.; Polanyi, J. C. In Progress in Reaction Kinetics, Porter, G., Ed.; Pergamon: Oxford, 1965; Vol. 3, pp 3-61.
106. (b) Levine, I. N. Physical Chemistry, 3rd ed.; McGraw-Hill: New York, 1988; pp. 783-796.
107. James, F. C.; Kerr, J. A.; Simons, J. P. J. Chem. Soc., Faraday Trans. 1, 1973, 2124-2129.
108. Sidebottom, H. W.; Badcock, C. C.; Jackson, G. E.; Calvert, J. G.; Reinhardt, G. W.; Damon, E. K. Environ. Sci. Technol. 1972, 6, 72.
109. (a) Hop, C. E. C. A.; Holmes, J. L. Int. J. Mass Spectrom. Ion Processes 1991, 104, 213.
110. (b) Turecek, F.; Gu, M.; Hop, C. E. C. A. J. Phys. Chem. 1995, 99, 2278-2291.
111. Nguyen, V. Q.; Shaffer, S. A.; Turecek, F.; Hop, C. E. C. A. J. Phys. Chem. 1995, 99, 15454-15464.
112. Nguyen, V. Q.; Turecek, F. J. Mass Spectrom. 1996, 31, 843-854.
113. (a) Muller, C.; Schweig, A. Tetrahedron 1973, 29, 3973.
114. (b) Solouki, B.; Bock, H.; Appel, R. Chem. Ber. 1975, 108, 897.
115. Dunbar, R. C. J. Chem. Phys. 1989, 90, 7369.
116. Lifshitz, C. Mass Spectrom. Rev. 1982, 1, 309.
117. Cosby, P. C. J. Chem. Phys. 1984, 81, 1102.