Meisenheimer complexes bonded at carbon and at oxygen

Journal of the American Society for Mass Spectrometry
Hao ChenR Graham Cooks

Abstract

The carbon-bonded gas-phase Meisenheimer complex of 2,4,6-trinitrotoluene (TNT) and the nitromethyl carbanion CH(2)NO(2)(-) (m/z 60) is generated for the first time by chemical ionization using nitromethane as the reagent gas. Collision-induced dissociation (CID) of the Meisenheimer complex furnishes deprotonated TNT, a result of the higher gas-phase acidity of TNT than nitromethane. The formation of Meisenheimer complexes with CH(2)NO(2)(-) in the gas phase is selective to highly electron-deficient compounds such as dinitrobenzene and trinitrobenzene and does not occur with organic molecules with lower electron-affinity such as methanol, methylamine, propionaldehyde, acetone, ethyl acetate, chloroform, toluene, m-methoxytoluene, and even nitrobenzene and p-fluoronitrobenzene. As such, the reaction allows selective detection of TNT in mixtures. Meisenheimer complexes between CH(2)NO(2)(-) and the three dinitrobenzene isomers display distinctive fragmentations. The oxygen-bonded sigma-complex of TNT with the deprotonated hemiacetal anion CH(3)OCH(2)O(-) (m/z 61), represents a different type of Meisenheimer complex. It displays characteristic fragmentation involving loss of HNO(2) upon CID. The combination of a selective ion/mole...Continue Reading

References

Jan 1, 1972·Pharmazie in unserer Zeit·K A Kovar
Oct 3, 2003·Nature·L A PinnaduwageJ D Adams
Jan 23, 2004·Chemical Communications : Chem Comm·Eduardo C MeurerR Graham Cooks
Mar 11, 2004·Chemical Communications : Chem Comm·Hao ChenR Graham Cooks
Aug 1, 1991·Journal of the American Society for Mass Spectrometry·T G HeathJ T Watson

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Citations

Sep 29, 2011·Journal of the American Society for Mass Spectrometry·John M GarverVeronica M Bierbaum
Mar 13, 2013·Journal of the American Society for Mass Spectrometry·Hao-Yang WangYin-Long Guo
Aug 21, 2013·Journal of the American Society for Mass Spectrometry·Barbara ChiavarinoMaria Elisa Crestoni
Oct 1, 2013·Journal of the American Society for Mass Spectrometry·Hao-Yang WangYin-Long Guo
Nov 3, 2004·Journal of the American Society for Mass Spectrometry·Hao ChenHabib Bagheri
Jan 18, 2006·Journal of the American Society for Mass Spectrometry·Hao-Yang WangLong Lu
Jun 9, 2007·Journal of the American Society for Mass Spectrometry·Witold DanikiewiczMagdalena Zimnicka
Apr 19, 2005·Chemical Communications : Chem Comm·Igor A PopovR Graham Cooks
Nov 21, 2012·The Journal of Chemical Physics·Maria Elisa CrestoniSimonetta Fornarini
Apr 22, 2015·Journal of the American Society for Mass Spectrometry·Magdalena Zimnicka, Witold Danikiewicz
Feb 10, 2017·Organic & Biomolecular Chemistry·Ryosuke MatsubaraMasahiko Hayashi
Dec 16, 2017·Environmental Science and Pollution Research International·Viji SelvarajViswanathan Chinnuswamy
Jun 23, 2009·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Kazuko InoueMasato Chiba
Feb 5, 2011·Mass Spectrometry Reviews·Marko MäkinenMika Sillanpää
Apr 9, 2015·Mass Spectrometry Reviews·Witold Danikiewicz, Magdalena Zimnicka
Mar 16, 2013·Journal of Mass Spectrometry : JMS·Cécile HubertJean-Claude Tabet
Feb 8, 2007·Angewandte Chemie·Barbara ChiavarinoPhilippe Maître
May 10, 2005·Journal of Mass Spectrometry : JMS
Nov 18, 2020·Physical Chemistry Chemical Physics : PCCP·Nishant SharmaUpakarasamy Lourderaj
Apr 1, 2010·The Journal of Organic Chemistry·Israel FernándezEinar Uggerud
May 8, 2013·The Journal of Organic Chemistry·Gavin O JonesHans W Horn
Oct 21, 2014·The Journal of Organic Chemistry·Scott GronertVeronica M Bierbaum

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