ArticleJournal of the American Society for Mass Spectrometry2007
Gas-phase smiles rearrangement reactions of deprotonated 2-(4, 6-dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide and its derivatives in electrospray ionization mass spectrometry.
Article in Journal of the American Society for Mass Spectrometry, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
5 citing papers in PubMed.
- Article
- The role of methoxy group in the Nazarov cyclization of 1,5-bis-(2-methoxyphenyl)-1,4-pentadien-3-one in the gas phase and condensed phase.Journal of the American Society for Mass Spectrometry · 2014Article
- Article
- Gas phase chemistry of Li+ with amides: the observation of LiOH loss in mass spectrometry.Journal of the American Society for Mass Spectrometry · 2012Article
- Deprotonated N-(2,4-Dinitrophenyl)amino Acids Undergo Cyclization in Solution and the Gas Phase.International journal of mass spectrometry · 2011Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The negative ions of deprotonated 2-(4, 6-dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide and its derivatives are studied by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Upon collisional activation, the [M - H](-) ions dissociate in two competitive pathways that can be considered as the gas-phase Smiles rearrangement reactions, giving rise to the characteristic fragment ions [M - H - C(7)H(4)OS](-) and [M - H - C(13)H(8)NSR](-) (R = substituent). Theoretical computations were invoked to shed light on the reaction mechanisms of the representative Compound 1 by the semiempirical PM3 method. These theoretical calculations show that the formation of [M - H - C(13)H(8)NSR](-) (R = H for Compound 1) is more favorable. Furthermore, it is found that the intensities of the two product ions are strongly influenced by the position and the nature of the substituents. For the para-substituted compounds, the ln[(M - H - C(7)H(4)OS(-))/(M - H - C(13)H(8)NSR(-))] values are well correlated with the sigma(p)(-) substituent constants. In addition, the dependence of the intensity ratios of these two ions, ln[(M - H- C(7)H(4)OS(-))/(M - H - C(13)H(8)NSR(-))](R = CH(3)), on the collision energy can be used to distinguish the positional isomers.
Indexed as
Identifiers
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.