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Type: Artigo de periódico
Title: Hydrogen/chlorine Exchange Reactions Of Gaseous Carbanions
Author: Chen H.
Cooks R.G.
Meurer E.C.
Eberlin M.N.
Abstract: Gas-phase reactions of three typical carbanions CH2NO 2 -, CH2CN-, and CH 2S(O)CH3 - with the chloromethanes CH 2Cl2, CHCl3, and CCl4, examined by tandem mass spectrometry, show a novel hydrogen/chlorine exchange reaction. For example, reaction between the nitromethyl anion CH2NO 2 - and carbon tetrachloride CCl4 forms the ion CHClNO2 -. The suggested reaction mechanism involves nucleophilic attack by CH2NO2 - at the chlorine of CCl4 followed by proton transfer within the resulting complex [CH2ClNO2 + CCl3 -] to form CHClNO2 - and CHCl3. Two other carbanions CH2CN- and CH2S(O)CH3 - also undergo the novel hydrogen/chlorine exchange reactions with CCl4 but to a much smaller extent, their higher nucleophilicities favoring competitive nucleophilic attack reactions. Proton abstraction is the exclusive pathway in the reactions of these carbanions with CHCl3. While CH2CN- and CH2S(O)CH3 - promote mainly proton abstraction and nucleophilic displacement in reactions with CH2Cl2, CH2NO2 - does not react. © 2005 American Society for Mass Spectrometry.
Citation: Journal Of The American Society For Mass Spectrometry. , v. 16, n. 12, p. 2045 - 2051, 2005.
Rights: fechado
Identifier DOI: 10.1016/j.jasms.2005.08.012
Date Issue: 2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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