Theoretical and experimental study of tropylium formation from substituted benzylpyridinium species

Journal of Mass Spectrometry

Volumn 44, Issue 1, 2009, Pages 12-17

  Zins, Emilie Laure ^a   Pepe, Claude ^a   Rondeau, David ^b   Rochut, Sophie ^a   Galland, Nicolas ^c   Tabet, Jean Claude ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ D'ANGERS   (France)

^c CNRS   (France)

Author keywords

Activation energy; Benzylpyridinium fragmentation; DFT calculations; FAB; MIKE; Tropylium formation

Indexed keywords

CHEMICAL BONDS; IONIZATION; KINETIC ENERGY; KINETICS; QUANTUM CHEMISTRY;

BENZYLPYRIDINIUM FRAGMENTATION; DFT CALCULATION; MIKE; QUANTUM CHEMICAL CALCULATIONS; REARRANGEMENT REACTIONS; THEORETICAL CALCULATIONS; THERMODYNAMICALLY STABLE; TROPYLIUM;

ACTIVATION ENERGY;

BENZYL DERIVATIVE; PYRIDINE DERIVATIVE; TROPYLIUM; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; DENSITY FUNCTIONAL THEORY; ENERGY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; IONIZATION; MOLECULAR STABILITY; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REACTION ANALYSIS; THEORETICAL STUDY; THERMODYNAMICS;

EID: 58249098569     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1461     Document Type: Article

References (35)

1. K. Vekey. Internal energy effects in mass spectrometry. Journal of Mass Spectrometry 1996, 31, 445.
2. M. Yamashita, J. B. Fenn. Electrospray ion source. Another variation on the free-jet theme. Journal of Physical Chemistry 1984, 88, 4451.
3. C. M. Whitehouse, R. N. Dreyer, M. Yamashita, J. B. Fenn. Electrospray interface for liquid chromatographs and mass spectrometers. Analytical Chemistry 1985, 57, 675.
4. V. Gabelica, E. De Pauw. Internal energy and fragmentation of ions produced in electrospray sources. Mass Spectrometry Reviews 2005, 24, 566.
5. L. Drahos, R. M. A. Heeren, C. Collette, E. De Pauw, K. Vekey. Thermal energy distribution observed in electrospray ionization. Journal of Mass Spectrometry 1999, 34, 1373.
6. J. Naban-Maillet, D. Lesage, A. Bossée Y. Guimbert, J. Sztaray, K. Vekey, JC. Tabet. Internal energy distribution in electrospray ionization. Journal of Mass Spectrometry 2005, 40, 1.
7. G. Luo, I. Marginean, A. Vertes. Internal energy of ions generated by matrix-assisted laser desorption/ionization. Analytical Chemistry 2002, 74, 6185.
8. V. Gabelica, E. De Pauw, M. Karas. Influence of the capillary temperature and the source pressure on the internal energy distribution of electrosprayed ions. International Journal of Mass Spectrometry 2004, 231, 189.
9. C. Collette, E. De Pauw. Calibration of the internal energy distribution of ions produced by electrospray. Rapid Communications in Mass Spectrometry 1998, 12, 165.
10. A. Hoxha, C. Collette, E. De Pauw, B. Leyh. Mechanism of collisional heating in electrospray mass spectrometry : ion trajectory calculations. Journal of Physical Chemistry A 2001, 105, 7326.
11. L. Drahos, E. De Pauw, K. Vekey. Comparison of the internal energy distributions of ions produced by different electrospray sources. Rapid Communications in Mass Spectrometry 1998, 12, 1673.
12. T. Baer, P. M. Mayer. Statistical Rice-Ramsperger-Kassel-Marcus quasiequilibrium theory calculations in mass spectrometry. Journal of the American Society for Mass Spectrometry 1997, 8, 103.
13. I. Oref,D. C. Tardy. Energy transfer in highly excited large polyatomic molecules. Chemical Reviews 1990, 90, 1407.
14. C. Lifshitz. Tropylium Ion Formation from Toluene: Solution of an Old Problem in Organic Mass Spectrometry. Accounts of Chemical Research 1994, 27, 138.
15. I. S. Ignatyev, T. Sundius. Competitive ring hydride shifts and tolylbenzyl rearrangements in tolyl andsilatolyl cations. Chemical Physics Letters 2000, 326, 101.
16. + ratios after charge transfer to ethylbenzene. Journal of Physical Chemistry A 2004, 108, 5600.
17. V. A. Kharlanov, W. Abraham, W. Rettig. Photophysics of arylsubstituted tropylium ions. Journal of Photochemistry and Photobiology A: Chemistry 2001, 143, 109.
18. J. H. Moon, J. C. Choe, M. S. Kim. Kinetic energy release distribution in the dissociation of toluene molecular ion. The Tropylium vs Benzylium story continues. Journal of Physical Chemistry A 2000, 104, 458.
19. +. Journal of Physical Chemistry A 2004, 108, 1574.
20. N. Athanassios, L. Radon. A Simple Failing of G2 Theory: Heats of Combustion. Journal of the American Chemical Society 1994, 116, 9769.
21. N. Athanassios, L. Radon. Classical and Nonclassical Isomers of Tropylium, Silatropylium,and Germatropylium Cations. Descending the Periodic Table Increases the Preference for Nonclassical Structures. Journal of the American Chemical Society 1997, 119, 11933.
22. R. Disselkamp, H. S. Im, R. Bernstein. Potential energy surfaces of substituted anilines : conformational energies, deuteriation effects, internal rotation, and torsional motion. Journal of Chemical Physics 1992, 97, 7889.
23. R. G. Cook, J. H. Beynon, R. H. Caprioli, G. R. Lester. Metastable Ions. Elsevier: Amsterdam, 1973.
24. T. Ast, M. Medved, J. Marsel. Ion kinetic energy spectroscopy study of doubly charged ion reactions in some mono and disubstituted benzenes. Croatica Chemica Acta 1977, 49, 425.
25. J. L. Holmes, J. K. Terlouw. The scope of metastable peack observations. Organic Mass Spectrometry 1980, 15, 383.
26. C. J. Proctor, A. G. Brenton, J. H. Beynon, B. Kralj, J. Marsel. An investigation into the reactivity of ions arising from different regions of a translational energy release distribution : a need for angular collimation. International Journal of Mass Spectrometry and Ion Physics 1980, 35, 393.
27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann Jr, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, 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, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople. Gaussian 03. Gaussian: Pittsburgh, 2002.
28. C. Peng, P. Ayala, H. B. Schlegel, M. J. Frisch. Using redundant internal coordinates to optimize equilibrium geometries and transition states. Journal of Computational Chemistry 1996, 17, 49.
29. T. A. Halgren, W. N. Lipscomb. The synchronous-transit method for determining reaction pathways and locating molecular transition states. Chemical Physics Letters 1977, 49, 225.
30. N. Govind, M. Petersen, G. Fitzgerald, D. King-Smith, J. Andzelm. A generalized synchronous transit method for transition state location. Computational Materials Science http://www.sciencedirect.com/science/ journal/09270256 2003, 28, 250.
31. D. H. Williams, S. Naylor. The internal energy distribution in fast atom bombardment/liquid secondary ion mass spectra. Journal of the Chemical Society, Chemical Communications 1987, 18, 1408.
32. J. L. Holmes, C. Aubry, P. M. Mayer (eds). Assigning Structures to Ions in Mass Spectrometry. CRC Press Taylor and Francis Group: FL, 2007.
33. L. B. Harding. Ab initio studies of (1,2)-hydrogen migrations in open-shell hydrocarbons : vinyl radical, ethyl radical and triplet methylcarbene. Journal of the American Chemical Society 1981, 103, 7469.
34. L. Valko, P. Simon, N. Van Cuong. Minimum-energy reaction path extended-BEBO study of (1,2)-hydrogen migration in trimethylene biradical. Chemical Physics Letters 1988, 146, 439.
35. K. N. Fan, Z. H. Li, W. N. Wang, H. H. Huang, W. Huang. A theoretical study on the isomerization of cyclopropane to propene with ab initio and DFT methods. Chemical Physics Letters 1997, 277, 257.