Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process

Sekiguchi O, Meyer V, Letzel M, Kuck D, Uggerud E (2009)
EUROPEAN JOURNAL OF MASS SPECTROMETRY 15(5): 167-181.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Sekiguchi, Osamu; Meyer, Verena; Letzel, MatthiasUniBi; Kuck, DietmarUniBi; Uggerud, Einar
Einrichtung
Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie
Abstract / Bemerkung
We report the unimolecular decomposition following collisional activation of protonated mono-, di- and trimethylbenzenes as a function of collision energy. The resulting energy-resolved mass spectra are then used for the quality control of high-level quantum chemical models of the respective potential energy surfaces. Distinction is made between direct dissociation products (CH4 or H-2) and indirect products (alkenes), since formation of the latter requires extensive rearrangement of the molecular skeleton. Very good consistency was found between model and experiment. The models thereby provide a solid foundation for discussing the reaction mechanisms of the industrial methanol-to-hydrocarbon process. The tosses of CH4, C2H4 and C3H6 from mesitylenium ions have been studied by C-13 and H-2 labelling and the alkene tosses were found to occur via irreversible isomerisation pathways.
Stichworte
methanol-to-hydrocarbons; methylbenzenes; gas-phase ion chemistry; alkylbenzenium ions; mass spectrometry; zeolite
Erscheinungsjahr
2009
Zeitschriftentitel
EUROPEAN JOURNAL OF MASS SPECTROMETRY
Band
15
Ausgabe
5
Seite(n)
167-181
ISSN
1356-1049
Page URI
https://pub.uni-bielefeld.de/record/1634738

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Sekiguchi O, Meyer V, Letzel M, Kuck D, Uggerud E. Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process. EUROPEAN JOURNAL OF MASS SPECTROMETRY. 2009;15(5):167-181.
Sekiguchi, O., Meyer, V., Letzel, M., Kuck, D., & Uggerud, E. (2009). Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process. EUROPEAN JOURNAL OF MASS SPECTROMETRY, 15(5), 167-181. https://doi.org/10.1255/ejms.953
Sekiguchi, Osamu, Meyer, Verena, Letzel, Matthias, Kuck, Dietmar, and Uggerud, Einar. 2009. “Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process”. EUROPEAN JOURNAL OF MASS SPECTROMETRY 15 (5): 167-181.
Sekiguchi, O., Meyer, V., Letzel, M., Kuck, D., and Uggerud, E. (2009). Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process. EUROPEAN JOURNAL OF MASS SPECTROMETRY 15, 167-181.
Sekiguchi, O., et al., 2009. Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process. EUROPEAN JOURNAL OF MASS SPECTROMETRY, 15(5), p 167-181.
O. Sekiguchi, et al., “Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process”, EUROPEAN JOURNAL OF MASS SPECTROMETRY, vol. 15, 2009, pp. 167-181.
Sekiguchi, O., Meyer, V., Letzel, M., Kuck, D., Uggerud, E.: Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process. EUROPEAN JOURNAL OF MASS SPECTROMETRY. 15, 167-181 (2009).
Sekiguchi, Osamu, Meyer, Verena, Letzel, Matthias, Kuck, Dietmar, and Uggerud, Einar. “Energetics and reaction mechanisms for the competitive losses of H-2, CH4 and C2H4 from protonated methylbenzenes-implications to the methanol-to-hydrocarbons (MTH) process”. EUROPEAN JOURNAL OF MASS SPECTROMETRY 15.5 (2009): 167-181.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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49 References

Daten bereitgestellt von Europe PubMed Central.


Farcaşiu, Acc. Chem. Res. 15(), 1982

Pfeiffer, Liebigs Ann. Chem. 461(), 1928

Williams, J. Am. Chem. Soc. 96(), 1974

Taylor, 1990

Olsbye, Catal. Today 106(), 2005

Dahl, Catal. Lett. 20(), 1993

Cui, Angew. Chem. 118(), 2006

McCann, Angew. Chem. 120(), 2008

Svelle, Catal. Lett. 109(), 2006

Arstad, J. Phys. Org. Chem. 17(), 2004

Kuck, 1990

Mormann, Int. J. Mass Spectrom. 267(), 2007

Mormann, J. Mass Spectrom. 34(), 1999

Mormann, Int. J. Mass Spectrom. 210(), 2001

Mormann, Int. J. Mass Spectrom. 219(), 2002

Mormann, Int. J. Mass Spectrom. 249(), 2006
The gas-phase basicity and proton affinity of 1,3,5-cycloheptatriene--energetics, structure and interconversion of dihydrotropylium ions.
Salpin JY, Mormann M, Tortajada J, Nguyen MT, Kuck D., Eur J Mass Spectrom (Chichester) 9(4), 2003
PMID: 12939488

Mormann, Eur. J. Mass Spectrom. 5(), 1999
The gas-phase basicity and proton affinity of 7-methyl-1,3,5-cycloheptatriene as determined by the thermokinetic method.
Mormann M, Kuck D., J Mass Spectrom 42(2), 2007
PMID: 17154351

Kuck, J. Am. Chem. Soc. 101(), 1979

Kuck, J. Chem. Soc. Perkin Trans. 2(), 1985

van, Recl. Trav. Chim. Pays-Bas 90(), 1971

Grover, Eur. Mass Spectrom. 2(), 1996

Frisch, 2004

Møller, Phys. Rev. 46(), 1934

Curtiss, J. Chem. Phys. 109(), 1998
Dissociation routes of protonated toluene probed by infrared spectroscopy in the gas phase.
Schroder D, Schwarz H, Milko P, Roithova J., J Phys Chem A 110(27), 2006
PMID: 16821818

Devlin, J. Am. Chem. Soc. 98(), 1976

Eckert-Maksić, 1995

Kuck, Angew. Chem. 112(), 2000

Dopfer, Int. J. Mass Spectrom. 249(), 2006

Cacace, J. Am. Chem. Soc. 114(), 1992

Kuck, 2002

Büker, Int. J. Mass Spectrom. Ion Processes 160(), 1997

Cooks, Org. Mass Spectrom. 7(), 1973

Uggerud, Mass Spectrom. Rev. 18(), 1999

Speranza, J. Am. Chem. Soc. 99(), 1977

Ausloos, Int. J. Mass Spectrom. Ion Processes 92(), 1989

Doering, J. Am. Chem. Soc. 76(), 1954

Lifshitz, Acc. Chem. Res. 27(), 1994

Kuck, 2005

Jackson, J. Am. Chem. Soc. 99(), 1977

Dunbar, J. Am. Chem. Soc. 95(), 1973

Kuck, J. Label. Comp. Radiopharm. 50(), 2007

Audier, New. J. Chem. 13(), 1989

Donchi, Int. J. Mass Spectrom. Ion Phys. 93(), 1989
Does an ethene/benzenium ion complex exist? A discrepancy between B3LYP and MP2 predictions.
Kolboe S, Svelle S., J Phys Chem A 112(29), 2008
PMID: 18593131

Denhez, New. J. Chem. 15(), 1991

Herman, Org. Mass Spectrom. 16(), 1981
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