1999
DOI: 10.1002/(sici)1099-1395(199911)12:11<819::aid-poc192>3.0.co;2-r
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Influence of the substituent on the major decomposition channels of the NO2 group inpara-substituted nitrobenzenes: a tandem mass spectrometric study

Abstract: The relative extents of loss of NO 2 and NO were determined by 70 eV electron ionization and tandem mass spectrometry using B/E linked scans to investigate metastable (unimolecular) and collision-induced dissociation processes for molecular ions formed by electron ionization of para-substituted nitrobenzene compounds. The substituents used (NO 2 , CHO, H, OCH 3 ) represent a wide range of electron donor-acceptor properties. Loss of NO 2 was favored by electron-withdrawing groups, while an electron-donor group … Show more

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Cited by 20 publications
(30 citation statements)
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“…These m / z 165 and m / z 152 fragment ions show a competition between the prompt isomerization of –NO 2 into –ONO leading to loss of NO • ( m / z 152), which is favored in comparison to the ‘ ortho effect’ hydrogen transfer leading to OH • release ( m / z 165, Table S3). Although the NO • loss, resulting from the NO 2 /ONO isomerization, has been observed in many other studies for radical anions, we show herein that this isomerization plays an important role during fragmentation of [M‐H] ‐ ions of nitrotoluenes.…”
Section: Resultssupporting
confidence: 43%
“…These m / z 165 and m / z 152 fragment ions show a competition between the prompt isomerization of –NO 2 into –ONO leading to loss of NO • ( m / z 152), which is favored in comparison to the ‘ ortho effect’ hydrogen transfer leading to OH • release ( m / z 165, Table S3). Although the NO • loss, resulting from the NO 2 /ONO isomerization, has been observed in many other studies for radical anions, we show herein that this isomerization plays an important role during fragmentation of [M‐H] ‐ ions of nitrotoluenes.…”
Section: Resultssupporting
confidence: 43%
“…Theoretical fragmentation of the conjugate in the positive mode was accomplished using the sequences for each peptide in the conjugate and the masses for each intervening chemical cross-link and its possible fragmentation products, using a mass error tolerance not exceeding 0.7 Da for each fragment ion. A modification table was generated for the DFDNB cross-linker based on the loss of NO 2 observed for structural analogs of the reagent (40,41). Potential matching ion assignments for each fragment mass generated by MS2Links were verified using a spreadsheet containing an array of masses predicted for the cross-linker (and fragments thereof) and also those generated for each peptide in the conjugate using MS Product, a fragmentation tool in Protein Prospector developed at the University of California, San Francisco (42).…”
Section: Methodsmentioning
confidence: 99%
“…In fact, a reliable model was more expected for the non-ortho than for the ortho molecules since many different reaction paths exist upon the nature of the substituent in ortho position from the nitro group (nitro, alcohol, amino…) [52] whereas all non-ortho nitroaromatic compounds follow the same decomposition process, C-NO 2 homolysis being evidenced in previous theoretical studies [60,61] as the main reaction path (without influence of the substituent nature in meta and para position to the nitro group). Besides the applicability domain analysis confirms this observation since the predictive power (R 2 in ) of models 2 (entire set) and 4 (ortho molecules) are low in their applicability domain, compared to the one of model 3 (non-ortho molecules).…”
Section: Ortho Compoundsmentioning
confidence: 97%