ArticleJournal of the American Society for Mass Spectrometry2013
Gas-phase fragmentations of anions derived from N-phenyl benzenesulfonamides.
Article in Journal of the American Society for Mass Spectrometry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 26 citations in OpenAlex.
- Evidence for Phytoremediation and Phytoexcretion of NTO from Industrial Wastewater by Vetiver Grass.Molecules (Basel, Switzerland) · 2020Article
- Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CHJournal of the American Society for Mass Spectrometry · 2019Article
- Intramolecular Halogen Atom Coordinated H Transfer via Ion-Neutral Complex in the Gas Phase Dissociation of Protonated Dichlorvos Derivatives.Journal of the American Society for Mass Spectrometry · 2017Article
- Formation of Carbamate Anions by the Gas-phase Reaction of Anilide Ions with CO2.Journal of the American Society for Mass Spectrometry · 2016Article
- Gas-Phase Fragmentation of Protonated N,2-Diphenyl-N'-(p-Toluenesulfonyl)Ethanimidamides: Tosyl Cation Transfer Versus Proton Transfer.Journal of the American Society for Mass Spectrometry · 2015Article
- Mass spectrometry and theoretical studies on N-C bond cleavages in the N-sulfonylamidino thymine derivatives.Journal of the American Society for Mass Spectrometry · 2015Article
- Low-energy collision-induced dissociation mass spectra of protonated p-toluenesulfonamides derived from aliphatic amines.Journal of the American Society for Mass Spectrometry · 2014Article
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4 authors at 1 institution in 1 country.
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Abstract
In addition to the well-known SO2 loss, there are several additional fragmentation pathways that gas-phase anions derived from N-phenyl benzenesulfonamides and its derivatives undergo upon collisional activation. For example, N-phenyl benzenesulfonamide fragments to form an anilide anion (m/z 92) by a mechanism in which a hydrogen atom from the ortho position of the benzenesulfonamide moiety is specifically transferred to the charge center. Moreover, after the initial SO2 elimination, the product ion formed undergoes primarily, an inter-annular H2 loss to form a carbazolide anion (m/z 166) because the competing intra-annular H2 loss is significantly less energetically favorable. Results from tandem mass spectrometric experiments conducted with deuterium-labeled compounds confirmed that the inter-ring mechanism is the preferred pathway. Furthermore, N-phenyl benzenesulfonamide and its derivatives also undergo a phenyl radical loss to form a radical ion with a mass-to-charge ratio of 155, which is in violation of the so-called "even-electron rule."
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