Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange

Kuck, Dietmar

Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange

Kuck D (1992)
International Journal of Mass Spectrometry and Ion Processes 117(1-3): 441-455.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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DOI

https://doi.org/10.1016/0168-1176(92)80107-C

URN

urn:nbn:de:0070-pub-17743110

Autor*in

Kuck, Dietmar^UniBi

Einrichtung

Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie

Abstract / Bemerkung

Metastable [M - H]+ ions of alpha,omega-diphenylalkanes C6H5(CH2)xC6H5 where x = 3-6 (structures 3-6 respectively), generated by hydride abstraction in the chemical ionization (i-butane) source, eliminate benzene after proton exchange between the aromatic rings. The proton exchange is slow for ions [3 - H]+ and [4 - H]+, but fast and apparently complete for ions [5 - H]+ and [6 - H]+. These observations, combined with collision activation experiments, suggest the cyclization of the [M - H]+ ions to isomeric protonated 1-phenylbenzocycloalkane and 1-benzylbenzocycloalkane derivatives, i.e. to [M1 + H]+ type ions, with a preference for protonated tetralin structures. Hydrogen exchange between the aliphatic chain and the rings is absent or negligible for [M - H]+ ions of 3-5 but is significant for ions [6 - H]+.

Stichworte

Cyclization; Gas phase; Mechanisms; Diphenylalkanes; Proton exchange

Erscheinungsjahr

1992

Zeitschriftentitel

International Journal of Mass Spectrometry and Ion Processes

Band

117

Ausgabe

1-3

Seite(n)

441-455

ISSN

0168-1176

Page URI

https://pub.uni-bielefeld.de/record/1774311

Zitieren

Kuck D. Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange. International Journal of Mass Spectrometry and Ion Processes. 1992;117(1-3):441-455.

Kuck, D. (1992). Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange. International Journal of Mass Spectrometry and Ion Processes, 117(1-3), 441-455. https://doi.org/10.1016/0168-1176(92)80107-C

Kuck, Dietmar. 1992. “Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange”. International Journal of Mass Spectrometry and Ion Processes 117 (1-3): 441-455.

Kuck, D., 1992. Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange. International Journal of Mass Spectrometry and Ion Processes, 117(1-3), p 441-455.

D. Kuck, “Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange”, International Journal of Mass Spectrometry and Ion Processes, vol. 117, 1992, pp. 441-455.

Kuck, D.: Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange. International Journal of Mass Spectrometry and Ion Processes. 117, 441-455 (1992).

Kuck, Dietmar. “Gaseous [M - H]+ ions of alpha,omega-diphenylalkanes: cyclization to [M + H]+ type ions of benzocycloalkanes as recognized by chain-length dependent proton exchange”. International Journal of Mass Spectrometry and Ion Processes 117.1-3 (1992): 441-455.

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