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Type: Artigo de periódico
Title: Hydrogen/chlorine exchange reactions of gaseous carbartions
Author: Chen, H
Cooks, RG
Meurer, EC
Eberlin, MN
Abstract: Gas-phase reactions of three typical carbanions CH2NO2-, CH2CN-, and CH2S(O)CH3- with the chloromethanes CH2Cl2, CHCl3, and CCl4 examined by tandem mass spectrometry, show a novel hydrogen/chlorine exchange reaction. For example, reaction between the nitromethyl anion CH2NC2- and carbon tetrachloride CCl4 forms the ion CHClNO2-. The suggested reaction mechanism involves nucleophilic attack by CH2NC2- 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.
Country: EUA
Editor: Elsevier Science Inc
Citation: Journal Of The American Society For Mass Spectrometry. Elsevier Science Inc, v. 16, n. 12, n. 2045, n. 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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