Proton induced methyl group shifts in gaseous xylenium ions. Distinguishing isomers by gas-phase titration

International Journal of Mass Spectrometry and Ion Processes

Volumn 160, Issue 1-3, 1997, Pages 167-181

  Büker, Heinz Hermann ^a   Grützmacher, Hans Friedrich ^a   Crestoni, Maria Elisa ^b   Ricci, Andreina ^b  

^a BIELEFELD UNIVERSITY   (Germany)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

1,2 Methyl shift; Alkylarenium ions; Ion molecule reaction; Mixture analysis; Proton transfer reaction

Indexed keywords

EID: 0000727242     PISSN: 01681176     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0168-1176(96)04518-1     Document Type: Article

References (63)

1. J. March, Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, 3rd edn., Wiley, New York, 1985.
2. M.T. Bowers (Ed.), Gas Phase Ion Chemistry, Vol. 2, Academic Press, New York, 1979.
3. (a) S.G. Lias, J.F. Liebman and R.D. Levine, J. Phys. Chem. Ref. Data, 13 (1984) 695.
4. (b) J.E. Szulejko and T.B. McMahon, J. Am. Chem. Soc., 115 (1993) 7839.
5. P. Kebarle, in J.M. Farrar and W.H. Saunders, Jr., (Eds.), Techniques for the Study of Ion Molecule Reactions, Wiley, New York, 1988.
6. (a) D.H. Aue, H.M. Webb and M.T. Bowers, J. Am. Chem. Soc., 98 (1976) 311.
7. (b) S.G. Lias, L.-A.-A. Jackson, H. Argentar and J.F. Liebman, J. Org. Chem., 50 (1985) 333.
8. (a) N.G. Adams and D. Smith, Int. J. Mass Spectrom. Ion Phys., 21 (1976) 349.
9. (b) J.M. van Doren, S.E. Barlow, C.H. DePuy and V.M. Bierbaum, Int. J. Mass Spectrom. Ion Processes, 81 (1987) 85.
10. (a) J. Long and B. Munson, J. Am. Chem. Soc., 95 (1973) 2427.
11. (b) S.A. McLuckey, D. Cammeron and R.G. Cooks, J. Am. Chem. Soc., 103 (1981) 1313.
12. D.K. Bohme, in P. Ausloos (Ed.), Interactions between Ions and Molecules, Plenum, New York, 1974.
13. T. Su and M.T. Bowers, Int. J. Mass Spectrom. Ion Phys., 12 (1973) 347.
14. T. Su and J. Cesnavich, J. Chem. Phys., 76 (1982) 5183.
15. H.H. Büker and H.-F. Grützmacher, Int. J. Mass Spectrom. Ion Processes, 109 (1991) 95.
16. A.G. Harrison, Chemical Ionization Mass Spectrometry, 2nd edn., CRC Press, Boca Raton, FL, 1992.
17. (a) A. Benninghoven, Trends Anal. Chem., 1 (1982) 311.
18. (b) K.L. Busch, J. Mass Spectrom., 30 (1995) 233.
19. (c) J. Grotemeyer, K. Boesl, K. Walter and E.W. Schlag, Org. Mass Spectrom., 21 (1986) 645.
20. (d) J. Grotemeyer and E.M. Schlag, Angew. Chem., 100 (1988) 447.
21. (e) M. Karras and F. Hillenkamp, Anal. Chem., 60 (1988) 2299.
22. M. Wilm and M. Mann, Anal. Chem., 68 (1996) 1.
23. P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
24. G.A. Olah, Angew. Chem., 107 (1995) 1519.
25. (a) E.E. Kingston, J.S. Shannon and M.J. Lacey, Org. Mass Spectrom., 18 (1983) 183.
26. (b) A. Maquestiau, R. Flammang, M. Flammang-Barbieux, H. Mispreuve, I. Howe and J. Beynon, Tetrahedron, 36 (1980) 1993.
27. (c) E. Uggerud, Mass Spectrom. Rev., 11 (1992) 389.
28. (a) G.A. Olah, Angew. Chem., 85 (1973) 183.
29. (b) R.J. Gillespie and T.E. Peel, Adv. Phys. Org. Chem., 9 (1971) 1.
30. (c) G.A. Olah, R.H. Schlosberg, D.P. Kelley and G.D. Mateescu, J. Am. Chem. Soc., 92 (1970) 2546.
31. (d) G.A. Olah, R.H. Schlosberg, R.D. Porter, Y.K. Mo, D.P. Kelly and G.D. Mateescu, J. Am. Chem. Soc., 94 (1972) 2034.
32. D. Kuck, Mass Spectrom. Rev., 9 (1990) 583.
33. F. Cacace, in P. Ausloos (Ed.), Kinetics of Ion-Molecule Reactions, Plenum, New York, 1979.
34. (a) F. Cacace, in P. Ausloos and S.G. Lias (Eds.), Structure/ Reactivity and Thermochemistry of Ions, D. Reidel, Dordrecht, 1987.
35. (b) F. Cacace, Acc. Chem. Res., 21 (1988) 215.
36. (a) G.A. Olah and Y.K. Mo, J. Am. Chem. Soc., 94 (1972) 9241.
37. (b) G.A. Olah and Y.K. Mo, J. Org. Chem., 38 (1973) 3212.
38. M. Attina, F. Cacace and A. Ricci, J. Am. Chem. Soc., 113 (1991) 5937.
39. (a) D. Berthomieu, H.E. Audier, J.P. Denhez, C. Monteiro and P. Morgues, Org. Mass Spectrom., 26 (1991) 271.
40. (b) D. Berthomieu, H.E. Audier, C. Monteiro and J.P. Denhez, Rapid Commun. Mass Spectrom., 5 (1991) 415.
41. (c) D. Berthomieu, V. Brenner, G. Ohanessian, J.P. Denhez, P. Millie and H.E. Audier, J. Am. Chem. Soc., 115 (1993) 2505.
42. (d) J.P. Deriliez, H.E. Audier and D. Berthomieu, Rapid Commun. Mass Spectrom., 9 (1995) 1210.
43. (e) C. Matthias and D. Kuck, Org. Mass Spectrom., 28 (1993) 1073.
44. H.H. Büker, Doctoral Thesis, Bielefeld, 1992.
45. P. Kofel, M. Allemann, H.P. Kellerhals and K.P. Wanczek, Int J. Mass Spectrom. Ion Processes, 65 (1985) 97.
46. D. Thölmann and H.-Fr. Grützmacher, J. Am. Chem. Soc., 113 (1991) 3281.
47. ORIGIN 3.5, Microcal™ Software Inc., Northampton, MA, USA.
48. H. Sievers, unpublished results from this laboratory, 1996.
49. (a) A.L. McClellan, Tables of Experimental Dipole Moments, Freeman, San Francisco, CA, 1963.
50. (b) Landolt-Bernstein, Atom- und Molekillphysik, 6th edn., Vol. 1, Part 3, Springer, Berlin, 1951.
51. K.J. Miller and J.A. Savchik, J. Am. Chem. Soc., 101 1979) 7206.
52. J.S. Brodbelt, C.-C. Liou and T. Donovan, Anal. Chem., 63 (1991) 1205.
53. J. Shen, R.C. Dunbar and G.A. Olah, J. Am. Chem. Soc., 96 (1974) 6227.
54. D.M. Brouwer, Reel. Trav. Chim. Pays-Bas, 87 (1968) 611.
55. F. Cacace, M.E. Crestoni and S. Fornarini, J. Am. Chem. Soc., 114 (1992) 6776.
56. (a) W.E. Fameth and J.I. Brauman, J. Am. Chem. Soc., 98 (1976) 7891.
57. (b) D.F. Hunt and S.K. Sethi, J. Am. Chem. Soc., 102 (1980) 6953.
58. (c) P. Ausloos and S.G. Lias, J. Am. Chem. Soc., 103 (1981) 3641.
59. (d) R.R. Squires, V.M. Bierbaum, J.J. Grabowski and C.H. DePuy, J. Am. Chem. Soc., 105 (1983) 5185.
60. (e) S.G. Lias, J. Phys. Chem., 88 (1984) 4401.
61. (f) D.K. Bohme, Int. J Mass Spectrom. Ion Processes, 115 (1992) 95.
62. (a) E.P. Hunter and S.G. Lias, J. Phys. Chem., 86 (1982) 2769.
63. (b) A.C. Hopkinson, G.I. Mackay and D.K. Bohme, Can. J. Chem., 57 (1979) 2996.