A neutralization-reionization mass spectrometric study of alkyl hydroperoxide cation radicals and four distinguishable [C,H3,O2]+ isomers

International Journal of Mass Spectrometry and Ion Processes

Volumn 153, Issue 2-3, 1996, Pages 173-199

  Schalley, Christoph A ^a   Schröder, Detlef ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Hydroperoxy methyl radical; Kinetic energy release; Methyl peroxy radical; Neutralization reionization mass spectrometry; Peroxide chemistry

Indexed keywords

EID: 0001387611     PISSN: 01681176     EISSN: None     Source Type: Journal    
DOI: 10.1016/0168-1176(96)04360-1     Document Type: Article

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30. 2] species: (a) R. Zellner and F. Ewig, J. Phys. Chem., 92 (1988) 2971. (b) S.P. Walch, Chem. Phys. Lett., 215 (1993) 81. (c) E. Sicilia, F.P. Di Maio and N. Russo, Chem. Phys. Lett., 225 (1994) 208. (d) W.H. Green, Int. J. Quantum Chem., 52 (1994) 837. (e) D. Shen, A. Moise and H.O. Pritchard, J. Chem. Soc., Faraday Trans., 91 (1995) 1425.
31. 2] species: (a) R. Zellner and F. Ewig, J. Phys. Chem., 92 (1988) 2971. (b) S.P. Walch, Chem. Phys. Lett., 215 (1993) 81. (c) E. Sicilia, F.P. Di Maio and N. Russo, Chem. Phys. Lett., 225 (1994) 208. (d) W.H. Green, Int. J. Quantum Chem., 52 (1994) 837. (e) D. Shen, A. Moise and H.O. Pritchard, J. Chem. Soc., Faraday Trans., 91 (1995) 1425.
32. 2] species: (a) R. Zellner and F. Ewig, J. Phys. Chem., 92 (1988) 2971. (b) S.P. Walch, Chem. Phys. Lett., 215 (1993) 81. (c) E. Sicilia, F.P. Di Maio and N. Russo, Chem. Phys. Lett., 225 (1994) 208. (d) W.H. Green, Int. J. Quantum Chem., 52 (1994) 837. (e) D. Shen, A. Moise and H.O. Pritchard, J. Chem. Soc., Faraday Trans., 91 (1995) 1425.
33. 2] species: (a) R. Zellner and F. Ewig, J. Phys. Chem., 92 (1988) 2971. (b) S.P. Walch, Chem. Phys. Lett., 215 (1993) 81. (c) E. Sicilia, F.P. Di Maio and N. Russo, Chem. Phys. Lett., 225 (1994) 208. (d) W.H. Green, Int. J. Quantum Chem., 52 (1994) 837. (e) D. Shen, A. Moise and H.O. Pritchard, J. Chem. Soc., Faraday Trans., 91 (1995) 1425.
34. 2] species: (a) R. Zellner and F. Ewig, J. Phys. Chem., 92 (1988) 2971. (b) S.P. Walch, Chem. Phys. Lett., 215 (1993) 81. (c) E. Sicilia, F.P. Di Maio and N. Russo, Chem. Phys. Lett., 225 (1994) 208. (d) W.H. Green, Int. J. Quantum Chem., 52 (1994) 837. (e) D. Shen, A. Moise and H.O. Pritchard, J. Chem. Soc., Faraday Trans., 91 (1995) 1425.
35. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
36. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
37. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
38. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
39. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
40. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
41. For example, see: (a) H. Niki, P.D. Maker, C.M. Savage and L.P. Breitenbach, J. Phys. Chem., 87 (1983) 2190. (b) D. Rhäsa and R. Zellner, Chem. Phys. Lett., 132 (1986) 474. (c) F. Ewig, D. Rhäsa and R. Zellner, Ber. Bunsenges. Phys. Chem., 91 (1987) 708. (d) P. Dagaut, T.J. Wallington and M.J. Kurylo, J. Phys. Chem., 92 (1988) 3833. (e) G.L. Vaghjiani and A.R. Ravishankara, J. Phys. Chem., 93 (1989) 1948. (f ) P.D. Lightfoot, P. Roussel, F. Caralp and R. Lesclaux, J. Chem. Soc., Faraday Trans., 87 (1991) 3213. (g) T.P.W. Jungkamp, A. Kukui and R.N. Schindler, Ber. Bunsenges, Phys. Chem., 99 (1995) 1057.
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43. For some examples, see: (a) T. Prüsse, A. Fiedler and H. Schwarz, Helv. Chim. Acta, 74 (1991) 1127. (b) K. Seemeyer, T. Prüsse and H. Schwarz, Helv. Chim. Acta, 76 (1993) 1632. (c) C.A. Schalley, D. Schröder and H. Schwarz, J. Am. Chem. Soc., 116 (1994) 11089, and references cited therein.
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51. (a) C.A. Schalley, R. Wesendrup, D. Schröder and H. Schwarz, Organometallics, in press.
52. (b) D.M. Davies and M.E. Deary, J. Chem. Soc., Perkin Trans. 2, (1992) 559.
53. This finding is supported by a detailed study of dimethylperoxide cation radicals. For this system it has been shown experimentally and theoretically that the structure of the cations is very close to that of the neutral counterparts: C.A. Schalley, H. Friedrichs, G. Hornung, R. Wesendrup, D. Schröder and H. Schwarz, in preparation.
54. For a discussion of the role of ion/dipole complexes in the unimolecular decompositions of dialkyl peroxide cation radicals, see: C.A. Schalley, A. Fiedler, D. Schröder and H. Schwarz, Helv. Chim. Acta, 78 (1995) 1999.
55. C.A. Schalley, D. Schröder and H. Schwarz, unpublished results.
56. +. are taken from E.E. Ferguson, J. Roncin and L. Bonazzola, Int. J. Mass Spectrom. Ion Processes, 79 (1987) 215. For symmetric dialkyl peroxides this effect is much more pronounced and clearly affects the mass spectrometric behavior of the corresponding cation radicals (see Refs. [17, 18]).
57. +.
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60. If not stated otherwise, thermochemical data have been taken from: (a) S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin and W.G. Mallard, Gas-Phase Ion and Neutral Thermochemistry, J. Phys. Chem. Ref. Data. Suppl. 1, (1988).
61. (b) S.G. Lias, J.F. Liebman, R.D. Levin and S.A. Kafafi, NIST Standard Reference Database, Positive Ion Energetics, Version 2.01, Gaithersburg, MD, January 1994.
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64. -1, see J.E. Szulejko and T.B. McMahon, J. Am. Chem. Soc., 115 (1993) 7839. (c) B.J. Smith and L. Radom, J. Am. Chem. Soc., 115 (1993) 4885. (d) J.W. Keister, J.S. Riley and T. Baer, J. Am. Chem. Soc., 115 (1993) 12613.
65. -1, see J.E. Szulejko and T.B. McMahon, J. Am. Chem. Soc., 115 (1993) 7839. (c) B.J. Smith and L. Radom, J. Am. Chem. Soc., 115 (1993) 4885. (d) J.W. Keister, J.S. Riley and T. Baer, J. Am. Chem. Soc., 115 (1993) 12613.
66. -1, see J.E. Szulejko and T.B. McMahon, J. Am. Chem. Soc., 115 (1993) 7839. (c) B.J. Smith and L. Radom, J. Am. Chem. Soc., 115 (1993) 4885. (d) J.W. Keister, J.S. Riley and T. Baer, J. Am. Chem. Soc., 115 (1993) 12613.
67. -1, see J.E. Szulejko and T.B. McMahon, J. Am. Chem. Soc., 115 (1993) 7839. (c) B.J. Smith and L. Radom, J. Am. Chem. Soc., 115 (1993) 4885. (d) J.W. Keister, J.S. Riley and T. Baer, J. Am. Chem. Soc., 115 (1993) 12613.
68. 4.
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73. Selected references: (a) J.K. Terlouw, C.G. de Koster, W. Heerma, J.L. Holmes and P.C. Burgers, Org. Mass Spectrom., 18 (1982) 222. (b) J.K. Terlouw, J. Wezenberg, P.C. Burgers and J.L. Holmes, J. Chem. Soc., Chem. Commun., (1983) 1121. (c) R. Postma, P.J.A. Ruttink, J.H. Van Lenthe and J.K. Terlouw, Chem. Phys. Lett., 156 (1989) 245. (d) R. Flammang, M. Plisnier, G. Leroy, M. Sana, M.T. Nguyen and L.G. Vanquickenborne. Chem. Phys. Lett., 186 (1991) 393. (e) N. Heinrich, T. Drewello, P.C. Burgers, J.C. Morrow, J. Schmidt, W. Kullik, J.K. Terlouw and H. Schwarz, J. Am. Chem. Soc., 114 (1992) 3776.
74. A.J.R. Heck, L.J. de Koning and N.M.M. Nibbering, J. Phys. Chem., 96 (1992) 8870.
75. M.M. Bursey, J.R. Hass, D.J. Harvan and C.E. Parker, J. Am. Chem. Soc., 101 (1979) 5485
76. +, and the result is qualitatively identical, although the signal-to-noise ratio was poor.
77. (a) W.J. Bouma, P.C. Burgers, J.L. Holmes and L. Radom, J. Am. Chem. Soc., 108 (1986) 1767.
78. (b) R. Feng, C. Wesdemiotis and F.W. McLafferty, J. Am. Chem. Soc., 109 (1987) 6521.
79. (a) C. Wesdemiotis and F.W. McLafferty, Tetrahedron Lett., 22 (1981) 3479.
80. (b) P.C. Burgers, A.A. Mommers and J L. Holmes, J. Am. Chem. Soc., 105 (1983) 5976.
81. + has been taken from Ref. [4(e)].
82. . reaction in a flow reactor: R. Humpfer, H. Oser and H.-H. Grotheer. Int J. Chem Kinet., 27 (1995) 577.
83. +.); see Ref. [23].
84. For a similar proposal, see: J. Hrusǎák, D. Schröder, T. Weiske and H. Schwarz, J Am. Chem. Soc. 115 (1993) 2015.