Formation of organoxenon dications in the reactions of xenon with dications derived from toluene

Chemistry - A European Journal

Volumn 17, Issue 14, 2011, Pages 4012-4020

  Zins, Emilie Laure ^a   Milko, Petr ^a   Schröder, Detlef ^a   Aysina, Julia ^b   Ascenzi, Daniela ^b   Žabka, Jan ^c   Alcaraz, Christian ^d,e   Price, Stephen D ^f   Roithová, Jana ^g  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b UNIVERSITY OF TRENTO   (Italy)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^d UNIVERSITÉ PARIS SUD   (France)

^e SYNCHROTRON SOLEIL   (France)

^f UNIVERSITY COLLEGE LONDON   (United Kingdom)

^g CHARLES UNIVERSITY   (Czech Republic)

Author keywords

density functional calculations; photoionization; reactive intermediates; toluene; xenon

Indexed keywords

CARBENES; COLLISIONAL STABILIZATION; DENSITY-FUNCTIONAL CALCULATIONS; DICATIONS; DIHYDROGEN; DOUBLE IONIZATION; ELECTROPHILES; EXPERIMENTAL CONDITIONS; RARE GAS; REACTIVE INTERMEDIATES; SEVEN-MEMBERED RINGS; STABLE ISOMERS; THEORETICAL STUDY; TRIPLE-QUADRUPOLE MASS SPECTROMETER;

BINDING ENERGY; DENSITY FUNCTIONAL THEORY; INERT GASES; IONIZATION OF GASES; ISOMERS; MASS SPECTROMETRY; PHOTOIONIZATION; REACTION INTERMEDIATES; TOLUENE;

XENON;

EID: 79952842876     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002556     Document Type: Article

References (86)

1. C. L. Ricketts, D. Schröder, C. Alcaraz, J. Roithová, Chem. Eur. J. 2008, 14, 4779-4783
2. J. Roithová, C. L. Ricketts, D. Schröder, Int. J. Mass Spectrom. 2009, 280, 32-37. See also
3. J. Roithová, C. L. Ricketts, D. Schröder, Coll. Czech. Chem. Commun. 2008, 73, 811-821.
4. D. Ascenzi, J. Roithová, D. Schröder, E. L. Zins, C. Alcaraz, J. Phys. Chem. A 2009, 113, 11204-11210
5. E. L. Zins, D. Schröder, J. Phys. Chem. 2010, 114, 5989-5996.
6. L. Pauling, J. Am. Chem. Soc. 1933, 55, 1895-1900
7. J. H. Holloway, E. G. Hoppe, Adv. Inorg. Chem. 1998, 46, 51-100
8. L. Graham, O. Graudejus, N. K. Jha, N. Barlett, Coord. Chem. Rev. 2000, 197, 321-324
9. K. O. Christe, Angew. Chem. 2001, 113, 1465-1467
10. Angew. Chem. Int. Ed. 2001, 40, 1419-1421
11. W. Grochala, Chem. Soc. Rev. 2007, 36, 1632-1655
12. L. Khriachtchev, M. Räsänen, R. B. Gerber, Acc. Chem. Res. 2009, 42, 183-191.
13. For rare gas-noble metal compounds, see
14. H. Fang, X. G. Zhang, Theor. Chem. Acc. 2009, 123, 443-453, and references therein. For van der Waals complexes of rare gases with halogens, see
15. T. Gonzalez-Lezana, M. I. Hernandez, G. Delgado-Barrio, P. Villarreal, Theochem. 1998, 433, 107-111.
16. J. Roithová, D. Schröder, Angew. Chem. 2009, 121, 8946-8948
17. Angew. Chem. Int. Ed. 2009, 48, 8788-8790
18. see also:, A. Cohen, J. Lundell, R. B. Gerber, J. Chem. Phys. 2003, 119, 6415-6417.
19. J. F. Lockyear, K. Douglas, S. D. Price, M. Karwowska, K. FijaÅkowski, W. Grochala, M. Remeš, J. Roithová, D. Schröder, J. Phys. Chem. Lett. 2010, 1, 358-362.
20. D. Ascenzi, P. Tosi, J. Roithová, C. L. Ricketts, D. Schröder, J. F. Lockyear, M. A. Parkes, S. D. Price, Phys. Chem. Chem. Phys. 2008, 10, 7121-7128.
21. D. Ascenzi, P. Tosi, J. Roithová, D. Schröder, Chem. Commun. 2008, 4055-4057.
22. J. Roithová, D. Schröder, Phys. Chem. Chem. Phys. 2007, 9, 731-738.
23. J. Roithová, D. Schröder, J. Am. Chem. Soc. 2006, 128, 4208-4209
24. J. Roithová, D. Schröder, Chem. Eur. J. 2007, 13, 2893-2902.
25. 2+ dications and their reactions with rare gases other than Xe, see:, E. L. Zins, D. Schröder, Int. J. Mass Spectrom. 2011, 299, 53-58
26. 2+ dications from cycloheptatriene, see: D. Ascenzi, E. L. Zins, J. Aysina, J. Žabka, C. Alcaraz, S. D. Price, J. Roithová, D. Schröder, unpublished results.
27. D. Schröder, H. Schwarz, J. Phys. Chem. A 1999, 103, 7385-7394
28. D. Schröder, Angew. Chem. 2004, 116, 1351-1353
29. Angew. Chem. Int. Ed. 2004, 43, 1329-1331.
30. J. Roithová, D. Schröder, P. Grüne, T. Weiske, H. Schwarz, J. Phys. Chem. A 2006, 110, 2970-2978.
31. Z. Herman, Int. Rev. Phys. Chem. 1996, 15, 299-324
32. Z. Herman, Phys. Essays 2000, 13, 480-488. See also
33. J. Roithová, H. Schwarz, D. Schröder, Chem. Eur. J. 2009, 15, 9995-9999.
34. J. Roithová, D. Schröder, J. Loos, H. Schwarz, H.-C. Jankowiak, R. Berger, R. Thissen, O. Dutuit, J. Chem. Phys. 2005, 122, 094306
35. R. D. Molloy, J. H. D. Eland, Chem. Phys. Lett. 2006, 421, 31-35.
36. C. Lifshitz, Acc. Chem. Res. 1994, 27, 138-144.
37. J. Roithová, Z. Herman, D. Schröder, H. Schwarz, Chem. Eur. J. 2006, 12, 2465-2471.
38. E.-L. Zins, C. Pepe, D. Schröder, Faraday Discuss. 2010, 145, 157-169.
39. K. M. Ervin, P. B. Armentrout, J. Chem. Phys. 1985, 83, 166-189
40. P. B. Armentrout, Int. J. Mass Spectrom. 2000, 200, 219-241.
41. 0=1.85 V corresponds to the inflexion point of the parent-ion curve, that is, the voltage at which the half of the ions are stopped in the octopole.
42. J. Roithová, H. Schwarz, D. Schröder, Chem. Eur. J. 2009, 15, 9995-9999.
43. J. Roithová, J. Žabka, Z. Herman, R. Thissen, D. Schröder, H. Schwarz, J. Chem. Phys. A 2006, 110, 6447-6453.
44. P. Milko, J. Roithová, D. Schröder, H. Schwarz, Int. J. Mass Spectrom. 2007, 267, 139-147.
45. R. C. Dunbar, J. Am. Chem. Soc. 1975, 97, 1382-1384
46. P. Ausloos, J. Am. Chem. Soc. 1982, 104, 5259-5265
47. D. Schröder, H. Florencio, W. Zummack, H. Schwarz, Helv. Chim. Acta 1992, 75, 1792-1797
48. I. Kretzschmar, D. Schröder, H. Schwarz, Int. J. Mass Spectrom. Ion Processes 1997, 167/168, 103-115
49. T. D. Fridgen, J. Troe, A. A. Viggiano, A. J. Midey, S. Williams, T. B. McMahon, J. Phys. Chem. A 2004, 108, 5600-5609.
50. B. Jagoda-Cwiklik, P. Jungwirth, L. Rulíšek, P. Milko, J. Roithová, J. Lemaire, P. Maitre, J. M. Ortega, D. Schröder, ChemPhysChem 2007, 8, 1629-1639.
51. Note that the term "termolecular" also includes reactions in which a metastable adduct formed in a bimolecular manner is stabilized by collision with a third body within its lifetime; see: S. P. Sander et al., JPL Publication No. 06-2, Evaluation 15, Section 2 "Termolecular reactions", Jet Propulsion Laboratory, California Institute of Technology, Pasadena (USA), 2010 ().
52. R. C. Dunbar, G. T. Uechi, B. Asamoto, J. Am. Chem. Soc. 1994, 116, 2466-2470
53. A. Gapeev, R. C. Dunbar, J. Phys. Chem. A 2000, 104, 4084-4088. See also
54. D. Schröder, R. Brown, P. Schwerdtfeger, H. Schwarz, Int. J. Mass Spectrom. 2000, 203, 155-163.
55. +), only one of the product ions (or the average of both) should be considered in the analysis to maintain normalization.
56. For a case in which an almost invisible intermediate plays a decisive role in product ion formation, see:, J. Schwarz, D. Schröder, H. Schwarz, C. Heinemann, J. Hrušák, Helv. Chim. Acta 1996, 79, 1110-1120.
57. For this method referred to as reactive monitoring with synchrotron radiation, see
58. D. Schröder, J. Loos, H. Schwarz, R. Thissen, O. Dutuit, P. Mourgues, H.-E. Audier, Angew. Chem. 2002, 114, 2867-2870
59. Angew. Chem. Int. Ed. 2002, 41, 2748-2751
60. D. Schröder, J. Loos, H. Schwarz, R. Thissen, O. Dutuit, J. Phys. Chem. A 2004, 108, 9931-9937
61. reference [1a]
62. reference [2a]
63. J. Roithová, D. Schröder, Chem. Listy 2009, 73, 636-640.
64. The yield of the organoxenon ions was significantly lower in the synchrotron studies because 1) the collision chamber of the instrument used at the synchrotron SOLEIL has a length of only 3 cm, compared with about 20 cm in the TSQ mass spectrometer and 2) the protection system of the ultra-high vacuum system of SOLEIL did not allow for compensation of the shorter collision chamber by accordingly elevated xenon pressures.
65. J. Roithová, J. Žabka, D. Ascenzi, P. Franceschi, C. L. Ricketts, D. Schröder, Chem. Phys. Lett. 2006, 423, 254-259
66. P. Milko, D. Schröder, K. Lemr, J. Žabka, C. Alcaraz, J. Roithová, Coll. Czech Chem. Commun. 2009, 74, 101-114.
67. J. Roithová, D. Schröder, Phys. Chem. Chem. Phys. 2007, 9, 2341-2349.
68. D. Kuck, Int. J. Mass Spectrom. 2002, 213, 101-144.
69. G. Bouchoux, M. Yáñez, O. Mó, Int. J. Mass Spectrom. 1999, 185/186/187, 241-251.
70. G. A. Olah, Angew. Chem. 1995, 107, 1519-1532
71. Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405
72. G. A. Olah, D. A. Klumpp, Superelectrophiles and Their Chemistry, Wiley, New York, 2007
73. D. A. Klumpp, Chem. Eur. J. 2008, 14, 2004-2015.
74. J. Roithová, D. Schröder, J. Míšek, I. G. Stará, I. Starý, J. Mass Spectrom. 2007, 42, 1233-1237.
75. O. Dutuit, Ion Dissociation and Ion-Molecule Reactions Studied with State-Selected Ions in Fundamentals of Gas Phase Ion Chemistry (Ed.:, K. R. Jennings,), Kluwer, Amsterdam, 1991, p. 21-54.
76. O. Dutuit, C. Alcaraz, D. Gerlich, P. M. Guyon, J. W. Hepburn, C. Métayer-Zeitoun, J. B. Ozenne, M. Schweizer, T. Weng, Chem. Phys. 1996, 209, 177-186
77. C. Alcaraz, C. Nicolas, R. Thissen, J. Žabka, O. Dutuit, J. Phys. Chem. A 2004, 108, 9998-10009.
78. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211
79. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
80. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-206
81. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
82. N. Godbout, D. R. Salahub, J. Andzelm, E. Wimmer, Can. J. Chem. 1992, 70, 560-571.
83. F. Blanco, M. Solimannejad, I. Alkorta, J. Elguero, Theor. Chem. Acc. 2008, 121, 181-196.
84. Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, Montgomery Jr. J.A., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
85. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161
86. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.