Mechanistic views on aromatic substitution reactions by gaseous cations

Mass Spectrometry Reviews

Volumn 15, Issue 6, 1996, Pages 365-389

  Fornarini, Simonetta ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; PHASE INTERFACES; PROTON TRANSFER; SUBSTITUTION REACTIONS;

AROMATIC SUBSTITUTION REACTIONS; GAS-PHASE REACTIONS; IONIC INTERMEDIATES; KINETIC ISOTOPE EFFECTS; MECHANISTIC STUDIES; PROTON TRANSFER REACTIONS; QUANTITATIVE STUDY; REACTIVITY PATTERN;

REACTION INTERMEDIATES;

EID: 84988369910     PISSN: 02777037     EISSN: 10982787     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2787(1996)15:6<365::AID-MAS2>3.0.CO;2-G     Document Type: Article

References (99)

1. Arshadi, M.; Johnels, D.; Edlund, U.; Ottosson, C.-H.; Cremer, D. “Solvated silylium cations: structure determination by NMR spectroscopy and the NMR/ab initio/IGLO method,” J. Am. Chem. SOC. 1996,118. 5120.
2. Attina, M.; Cacace, F.; Ricci, A. “Gas phase alkylation of phenyltrimethylsilanes. Using the trimethylsilyl group to probe proton shifts in gaseous arenium ions,” J. Am. Chem. SOC. 1991,113, 5937.
3. Ausloos, P.; Lias, S. “Structure and reactivity of hydrocarbon ions” In Ion-Molecule Reactions Vol. II; Franklin, J. L., Ed.; Plenum Press: New York, 1972.
4. Ausloos, P.; Lias, S. G.; “Therrnoneutral isotope exchange reactions of cations in the gas phase,” J. Am. Chem. Soc. 1981, 103, 3641.
5. Bather, W.; Kuck, D.; Griitzmacher, H.-F. “Substituent effects on the intramolecular proton transfer in w-phenylalkylbenzenium ions,” Org. Mass Spectrom. 1985, 20, 589.
6. Berthomieu, D.; Audier, H.; Denhez, J. P.; Monteiro, C.; complexes intermediate in the reactions of protonated propylbenzenes,” Org. Mass Spectrom. 1991, 26, 271.
7. Berthomieu, D.; Brenner, V.; Ohanessian, G.; Denhez, J. P.; Millie, P.; Audier, H. “Ion-neutral complexes of protonated alkylbenzenes: experimental and theoretical studies,” J. Phys. Chem. 1995,99, 712.
8. Bowers, M. T.; Su, T. “Theory of ion polar molecule collisions,” In Interactions between Ions and Molecules: Ausloos, P., Ed.; Plenum Press: New York, 1975.
9. Bruins, A. P.; Nibbering, N. M. M. “Hydrogen scrambling in the long-lived protonated benzene ion generated from benzyl amine in the ICR spectrometer,” Org. Mass Spectrom. 1976, 11, 950.
10. Buker, H. H.; Griitzmacher, H.-F. “A FT-ICR study of steric effects on proton transfer reactions of polyalkyl benzenes,” Int. J. Mass Spectrom. Ion Processes 1991, 109, 95.
11. Cacace, F. “Recent radiolytic studies on the mechanism of gas phase ionic reactions,” Radiat. Phys. Chem. 1982, 20, 99.
12. Cacace, F. “Intramolecular selectivity, stereochemical and steric aspects of ion-molecule reactions.” In Kinetics of Ion-Molecule Reactions; Ausloos, P., Ed.; Plenum Press: New York, 1979.
13. Cacace, F. “The radiolytic approach to gas phase ion chemistry,” Acc. Chem. Res. 1988, 21, 215.
14. Cacace, F. “On the formation of adduct ions in gas phase aromatic substitution,” J. Chem. SOC. Perkin Trans. 2 1982, 1129.
15. + σ complexes in the gas phase,” Angew. Chem. Int. Ed. Engl. 1995,34, 654.
16. Cacace, F.; Crestoni, M. E.; de Petris, G.; Fomarini, S.; Grandinetti, F. “A comparative study of gas phase aromatic de-silylation and de-tert-butylation by charged electrophiles,’ ’ Can. J. Chem. 1988, 66, 3099.
17. Cacace, F.; Crestoni, M. E.; Fornarini, S. “Cationic aromatic silylation in the gas phase,” Znr. J. Mass Spectrom. Ion Processes 1988, 84, 17.
18. + cations,” J. Am. Chem. SOC. 1992,114, 6776.
19. Cacace, F.; Crestoni, M. E.; Fomarini, S.; Kuck, D. “Interannular proton transfer in thermal arenium ions from the gas-phase alkylation of 1,2-diphenylethane,” J. Am. Chem. SOC. 1993, 115, 1024.
20. + ions,” J. Phys. Chem. 1994, 98, 1641.
21. Cacace, F.; Crestoni, M. E.; Di Marzio, A.; Fomarini, S. “Gas Phase aromatic substitution. Reactivity of (trifluoromethoxy)-benzene toward charged electrophiles,” J. Phys. Chem. 1991, 95, 8731.
22. Cacace, F.; de Petris, G.; Fomarini, S.; Giacomello, P. “Gas phase cationic methylation of biphenyl and methylbiphenyls. A mass spectrometric and radiolytic study,” J. Am. Chem. Soc. 1986,108, 7495.
23. +) toward arenes,” J. Am. Chem. SOC. 1992, 114, 2002.
24. + displacement,” Organometallics 1995, 14, 2624.
25. +: benzenium ions. A combined approach by radiolytic, FA-SIFT, and FTICR methodologies,” J. Phys. Chem. 1996, 100, 16201.
26. +] non-covalent complexes in the gas phase (trifluor0)methylation of tert-butyl-substituted diphenylalkanes,” Int. J. Mass Spectrom. Ion Processes 1995,148, 215.
27. +: ions,” J. Phys. Chem. 1993, 97, 6197.
28. Crestoni, M. E.; Fomarini, S. “Gas phase reactions of charged electrophiles with styrene and phenylacetylene,” J. Am. Chem. Soc. 1989, 111, 6008.
29. + ions. Kinetic role of deprotonation of intermediate arenium ions,” J. Am. Chem. SOC. 1994, 116, 5873.
30. Crestoni, M. E.; Fornarini, S. “Long-lived @so-silylated p-toluenium ions: evidence from a kinetic isotope effect,” Angew. Chem. I&. Ed. Engl. 1994,33, 1094.
31. + ions,” J. Phys. Chem. 1995, 99, 3144.
32. Crestoni, M. E.; Fornarini, S.; Kuck, D. “Gas-phase protonation of α,ω-diphenylakanes,” J. Phys. Chem. 1995, 99, 3150.
33. 3 (x = 0, 1) with cationic electrophiles,” J. Organomet. Chem. 1994, 465, 109.
34. + (x = 1-6) benzenium ions: a flowing afterglow-selected ion flow tube study,” Int. J. Mass Spectrom. Zon Processes 1997, 151, 43.
35. Dunbar, R. C.; Uechi, G. T.; Asamoto, B. “Radiative association reactions of silicon and transition metal cations with the PAH compounds benzene, naphthalene, and anthracene,” J. Am. Chem. SOC. 1994,116, 2466.
36. Eabom, C. “Cleavages of aryl-silicon and related bonds by electrophiles,” J. Organomet. Chem. 1975, 100, 43.
37. 2O in the gas phase by ion cyclotron resonance spectroscopy,” J. Am. Chem. SOC. 1975, 97, 6893.
38. Fornarini, S. “Direct aromatic substitution by trimethylsilyl cations,” J. Org. Chem. 1988, 53, 1314.
39. Fomarini, S.; Muraglia, V. “Direct evidence for the existence and the relative stability of gaseous ethylenebenzenium ions from a ‘%labeling study,” J. Am. Chem. SOC. 1989, 111, 873.
40. Glukhovstev, M. N.; Pross, A.; Nicolaides, A.; Radom, L. “Is the most stable gas phase isomer of the benzenium cation a face protonated.ir-complex?” J. Chem. SOC. Chem. Cornmun. 1995,2347.
41. + A kinetic model for isotope exchange reactions,” Int. J. Mass Spectrom. Ion Processes, 1991, 109, 105.
42. n,” J.Phys. Chem. 1996,100, 5245.
43. Hrus&, J.; Schoder, D.; Weiske, T.; Schwarz, H. “Combined ab initio MO and experimental studies on the unimolecular HF loss from protonated fluorobenzene in the gas phase,” J. Am. Chem. SOC. 1993, 115, 2015.
44. Hunt, D. F.; Sethi, S. K. “Gas phase ion molecule isotope exchange reactions: methodology for counting hydrogen atoms in specific organic structural environments by chemical ionization mass spectrometry,” J. Am. Chem. SOC. 1980,102, 6953.
45. Jasinski, J. M.; Brauman, J. I. “Rates of proton transfer between pyridine bases in the gas phase. Steric and isotope effects,” J. Am. Chem. SOC. 1980, 102, 2906.
46. Keese, R. G.; Castleman, A. W. “Thermochemical data on gasphase ion-molecule association and clustering reactions,” J. Phys. Chem. Re$ Data 1986, 15, 1011.
47. + substitution in the gas phase,” J. Am. Chem. SOC. 1993, 115, 1004.
48. Kuck, D. “Ring-to-ring proton exchange in di-and oligophenylalkanes upon gas-phase protonolysis,” Int. J. Mass Spectrom. Ion Phys. 1983, 47, 499.
49. Kuck, D. “Mass spectrometry of alkylbenzenes and related compounds. Part 11. Gas-phase ion chemistry of protonated alkylbenzenes (alkylbenzenium ions),” Mass Spectrom. Rev. 1990, 9, 583.
50. Kuck, D.; Bather, W. “Inter-and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane),” Org. Mass Spectrom. 1986, 21, 451.
51. Kuck, D.; Bather, W.; Griitzmacher, H.-F. “Intramolecular ringto-ring proton transfer in gaseous (w-phenylalky1)benzenium ions,” J. Am. Chem. SOC. 1979, 101, 7154.
52. Kuck, D.; Bather, W.; Grutzmacher, H.-F. “Interannular proton exchange in protonated long-chain 1,w-diphenylalkanes,” Int. J. Mass Spectrom. Ion Processes 1985, 67, 75.
53. Kuck, D.; Ingemann, S.; de Koning, L.; Grutzmacher, H.-F.; Nibbering, N. M. M. “Proton exchange between arenium ions and arenes in the gas phase,” Angew. Chem. Int. Ed. Engl. 1985, 24, 693.
54. Kuck, D.; Matthias, C. “Formation of gaseous π and ion neutral complexes as probed by interannular tert-butyl cation transfer in protonated tert-butyl-substituted diphenylalkanes,” J. Am. Chem. SOC. 1992, 114, 1901.
55. Kuck, D.; Schneider, J.; Griitzmacher, H.-F. “A study of gaseous benzenium and toluenium ions generated from 1,4-dihydroand l-methyl-l,4-dihydro-benzoiacc ids,” J. Chem. SOC.P erkin Trans. 2 1985, 689.
56. Kuck, D.; Tholmann, D.; Grutzmacher, H.-F. “Fast interannular proton transfer in gaseous protonated a,w-diphenylalkanes: stereocontrol by the cyclohexane-l,4-diyl unit,” J. Chem. SOC. Perkin Trans. 2 1990, 251.
57. Lambert, J. B.; Zhang, S.; Stem, C. L.; Huffman, J. C. “Crystal structure of a silyl cation with no coordination to anion and distant coordination to solvent,” Science 1993, 260, 1917.
58. Lambert, J. B.; Zhang, S. “Triethylsilyl cations,” Science 1994, 263, 984.
59. + ions (ArH = benzene, toluene) formed by association and by protonation,” Can. J. Chem. 1992, 70, 2070.
60. Lias, S. G. “Ion-molecule reactions in radiation chemistry,” In Interactions between Ions and Molecules; Ausloos, P., Ed.; Plenum Press: New York, 1975.
61. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, N. G. “Gas-phase ion and neutral thermochemistry,” J. Phys. Chem. Ref Data, Suppl. I 1988, 17.
62. + ions exist in solution?” J. Chem. SOC. Dalton Trans. 1992, 1333.
63. Lin, Y.; Ridge, D. P.; Munson, B. “Association reactions of trimethylsilyl ions,” Org. Mass Spectrom. 1991, 26, 550.
64. Maerker, C.; Kapp, J.; Schleyer, P. v. R. “The nature of organosilicon cations and their interactions.” In Organosilicon Chemistry II; Auner, N.; Weis, J.; Eds.; VCH: Weinheim, 1996.
65. Martinsen, D. P.; Buttrill, S. E. “Determination of the site of protonation of substituted benzenes in water chemical ionization mass spectrometry,” Org. Mass Spectrom. 1976, 11, 762.
66. Mason, R. S.; Femandez, M. T.; Jennings, K. R. “Thermodynamics of some proton transfer reactions,” J. Chem. SOC., Faraday Trans. 1987, 83, 89.
67. Mason, R. S.; Williams, C. M.; Anderson, P. D. J. “The face centered 7r-complex isomer of the benzenium ion is probably the most stable form in the gas phase: experimental evidence,” J. Chem. SOC. Chem. Commun. 1995, 1027.
68. Matthias, C.; Kuck, D. “Intermediate ion-neutral complexes formed during the gas phase protonolysis of p-(tert-buty1)-substituted a,w-diphenylalkanes,” Org. Mass Spectrom. 1993, 28, 1073.
69. Matthias, C.; Weniger, K.; Kuck, D. “Regioselective hydride abstraction and proton transfer in gaseous ion/molecule complexes: methyl substituent effects on the fragmentation of protonated 1-(4-tert-butylphenyl)-3-phenylpropanes,” Eur. Mass Spectrom. 1995, I, 445.
70. McMahon, A. W.; Chadikun, F.; Harrison, A. G. “Site of protonation of aromatic compounds: a neutralization-reionization study,” Int. J. Mass Spectrom. Ion Processes 1989, 87, 275.
71. Melander, L.; Saunders, W. H. Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980.
72. Meot-Ner, M.; Hamlet, P.; Hunter, E. P.; Field, F. H. “Bonding energies in association ions of aromatic compounds. Correlations with ionization energies,” J. Am. Chem. Soc. 1978,100, 5466.
73. Morton, T. H. “The reorientation criterion and positive ion-neutral complexes,” Org. Mass Spectrom. 1992, 27, 353.
74. 3-catalyzed trialkysilylation of benzene and toluene with chlorotrialkylsilanes in the presence of Hiinig bases,” (hindered tertiary amines) J. Org. Chem. 1989, 54, 3770.
75. Olah, G. A.; Rasul, G.; Li, X.; Buchholz, H. A.; Sandford, G.; Prakash, G. K. S. “Triethylsilyl cations,” Science 1994,263, 983.
76. Olah, G. A.; Schlosberg, R. H.; Porter, R. D.; Mo, Y. K.; Kelly, D. P.; Mateescu, G. D. “Stable carbocations. The benzenium ion and monoalkylbenzenium ions,” J. Am. Chem. Soc. 1972, 94, 2034.
77. Olah, G. A.; Surya Prakash, G. K.; Sommer, J. Superacids; Wiley: New York, 1985.
78. Parry, A.; Fernandez, M. T.; Garley, M.; Mason, R. “Thermodynamic studies of gas-phase proton transfer equilibria involving benzene: a reassessment of earlier data,” J. Chem. Soc., Faraday Trans. 1992,88, 3331.
79. Pauling, L. “Triethylsilyl cations,” Science 1994, 263, 983.
80. Redman, E. W.; Johri, K. K.; Morton, T. H. “Structures of organic cations in the gas phase. Neutral products from fluoride abstraction examined by NMR,” J. Am. Chem. Soc. 1985, 107, 780.
81. +),” Science 1993,262, 402.
82. Reed, C. A.; Xie, Z. “Triethylsilyl cations,” Science 1994,263, 985.
83. Roberts, R. M.; Khalaf, A. A. Friedel Crafts Alkylation Chemistry; Marcel Dekker: New York, 1984.
84. Schleyer, P. v. R.; Buzek, P.; Miiller, T.; Apeloig, Y.; Siehl, H.-U. “The search for an isolable silyl cation must continue,” Angew. Chem. Int. Ed. Engl. 1993,32, 1471.
85. Schofield, K. Aromatic Nitration; Cambridge University Press: Cambridge, 1980.
86. Schwarz, H. “Positive and negative ion chemistry of silicon containing molecules in the gas phase.” In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1989.
87. Sen Sharma, D. K.; Ikuta, S.; Kebarle, P. “Alkylation of benzene by alkyl cations. Stability of the tert-butylbenzenium ion,” Can. J. Chem. 1982, 60, 2325.
88. Sieber, S.; Schleyer, P. v. R. “The accurate C2” phenonium and benzenonium ion structures confirmed by correlated GIAOMP2 NMR chemical shift calculations,” J. Am. Chem. Soc. 1993,115, 6987.
89. + complexes,” J. Am. Chem. Soc. 1995, i17, 2313.
90. Smith, R. L.; Chyall, L. J.; Beasley, B. J.; Kenttamaa, H. “The site of protonation of aniline,” J. Am. Chem. Soc. 1995, 117, 7971.
91. Speranza, M. “Kinetics and mechanisms in gas-phase ion chemistry by radiolytic methods,” Mass Spectrom. Rev. 1992, 11, 73.
92. + system,” Int. J. Mass Spectrom. Ion Processes 1995, 149l1.50, 1.
93. 6,” Org. Muss Spectrom. 1993, 28, 11 19.
94. + to toluene and benzene,” Int. J. Mass Spectrom. Ion Processes 1991, 109, 247.
95. Sunner, J. A.; Hiraoka, K.; Kebarle, P. “Hydride transfer reactions: temperature dependence of rate constants for isopropyl (1+) + isobutane = propane + tert-butyl (l+): clusters of isopropyl (1 +) and tert-butyl (1 +) with propane and isobutane,” J. Phys. Chem. 1989, 93, 4010.
96. Taylor, R. Electrophilic Aromatic Substitution; Wiley: Chichester, 1990.
97. Thibblin, A.; Ahlberg, P. “Reaction branching and extreme kinetic isotope effects in the study of reaction mechanisms,” Chem. Soc. Rev. 1989,18, 209.
98. Tkaczyk, M.; Harrison, A. G. “Site of protonation of fluorobenzenes by gaseous Bronsted acids,” int. J. Mass Spectrom. Ion Processes 1994, 132, 73.
99. Wojtyniak, A. C. M.; Stone, J. A. “A high pressure mass spectrometric study of the binding of trimethylsilylium to oxygen and aromatic bases,” Int. J. Mass Spectrom. Ion Processes 1986, 74, 59.