ArticleJournal of the American Society for Mass Spectrometry2006
Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution.
Article in Journal of the American Society for Mass Spectrometry, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 36 citations in OpenAlex.
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- Mass spectrometric study of the gas-phase difluorocarbene expulsion of polyfluorophenyl cations via F-atom migration.Journal of the American Society for Mass Spectrometry · 2013Article
- Study of the gas-phase intramolecular aryltrifluoromethylation of phenyl(trifluoromethyl)iodonium by ESI-MS/MS.Journal of the American Society for Mass Spectrometry · 2013Article
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- Gas phase decarbonylation and cyclization reactions of protonated N-methyl-N-phenylmethacrylamide and its derivatives via an amide Claisen rearrangement.Journal of the American Society for Mass Spectrometry · 2012Article
- Gas phase chemistry of Li+ with amides: the observation of LiOH loss in mass spectrometry.Journal of the American Society for Mass Spectrometry · 2012Article
- Integration of high accuracy N-terminus identification in peptide sequencing and comparative protein analysis via isothiocyanate-based isotope labeling reagent with ESI ion-trap TOF MS.Journal of the American Society for Mass Spectrometry · 2011Article
- Gas-phase smiles rearrangement reactions of deprotonated 2-(4, 6-dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide and its derivatives in electrospray ionization mass spectrometry.Journal of the American Society for Mass Spectrometry · 2007Article
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Authors and funding
5 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Tandem mass spectrometry is used to predict the chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives. Compound 1, N-2-2-4,6- dimethoxypyrimidin-2-yloxy benzylamino phenyl benzamide was selected as a model to present our idea. The CID reactions of protonated 1 include an intramolecular S(N)2 reaction and a cyclodehydration reaction. Under in-source CID conditions, deprotonated 1 undergoes a Smiles rearrangement reaction and then dissociates to the ion at m/z 349. Theoretical computations were invoked to shed light on the reaction mechanisms of 1 by the semiempirical PM3 method. These studies of gas-phase reactions show the reactivity of some potential reaction centers in this molecule, which inspired us to explore the solution phase analogous reactions of 1. Further experiments show that 1 has two analogous reactions in acidic solution: the acid-catalyzed cyclodehydration reaction and the acid-catalyzed Smiles rearrangement reaction. Moreover, 1 undergoes the base-catalyzed Smiles rearrangement under basic conditions. The present study demonstrates that mass spectrometry can play an important role in predicting the chemical solution phase transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives.
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