Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives

Kuck D, Heitkamp S, Letzel M, Ahmed I, Krohn K (2018)
EUROPEAN JOURNAL OF MASS SPECTROMETRY 24(1): 23-32.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Kuck, DietmarUniBi; Heitkamp, SandraUniBi; Letzel, Matthias; Ahmed, Ishtiaq; Krohn, Karsten
Abstract / Bemerkung
The electrospray ionization-collision-induced dissociation mass spectra of nine pyrogallol tribenzyl ethers, 2-10, and a catechol dibenzyl ether, 11, that bear various functional groups or larger structural extensions have been studied with respect to the occurrence of a highly characteristic consecutive loss of two benzyl radicals from the sodiated molecular ions, [M + Na](+). It is shown that this specific fragmentation reaction strongly dominates other fragmentation routes, such as loss of carbon monoxide, formaldehyde and water. In addition, elimination of benzaldehyde occurs as a minor fragmentation channel in most cases. In contrast to these aryl-benzyl ethers, the consecutive two-fold loss of C7H7 center dot is suppressed in the [M + Na](+) ions of dibenzyl ethers derived from multiply benzylated gallocatechin and catechin, where the elimination of benzyl alcohol prevails the primary fragmentation almost completely. The secondary fragmentation of the [M + Na](+) ions, which also comprises the two-fold loss of C7H7 center dot, as well as a remarkable primary fragmentation of a flavene-based congener leading to particularly stable sodium-free chromylium product ions is also presented.
Stichworte
Electrospray mass spectrometry; collision-induced dissociation; benzyl; aryl ethers; benzyl radicals; phenoxy radicals; homolytic cleavage; benzoquinones; sodiated molecules
Erscheinungsjahr
2018
Zeitschriftentitel
EUROPEAN JOURNAL OF MASS SPECTROMETRY
Band
24
Ausgabe
1
Seite(n)
23-32
ISSN
1469-0667
eISSN
1751-6838
Page URI
https://pub.uni-bielefeld.de/record/2919317

Zitieren

Kuck D, Heitkamp S, Letzel M, Ahmed I, Krohn K. Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives. EUROPEAN JOURNAL OF MASS SPECTROMETRY. 2018;24(1):23-32.
Kuck, D., Heitkamp, S., Letzel, M., Ahmed, I., & Krohn, K. (2018). Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives. EUROPEAN JOURNAL OF MASS SPECTROMETRY, 24(1), 23-32. doi:10.1177/1469066717729300
Kuck, D., Heitkamp, S., Letzel, M., Ahmed, I., and Krohn, K. (2018). Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives. EUROPEAN JOURNAL OF MASS SPECTROMETRY 24, 23-32.
Kuck, D., et al., 2018. Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives. EUROPEAN JOURNAL OF MASS SPECTROMETRY, 24(1), p 23-32.
D. Kuck, et al., “Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives”, EUROPEAN JOURNAL OF MASS SPECTROMETRY, vol. 24, 2018, pp. 23-32.
Kuck, D., Heitkamp, S., Letzel, M., Ahmed, I., Krohn, K.: Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives. EUROPEAN JOURNAL OF MASS SPECTROMETRY. 24, 23-32 (2018).
Kuck, Dietmar, Heitkamp, Sandra, Letzel, Matthias, Ahmed, Ishtiaq, and Krohn, Karsten. “Consecutive loss of two benzyl radicals from the [M + Na](+) adduct ions of pyrogallol tribenzyl ether and its derivatives”. EUROPEAN JOURNAL OF MASS SPECTROMETRY 24.1 (2018): 23-32.

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