Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/69001
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
Rights: fechado
Identifier DOI: 10.1016/j.jasms.2005.08.012
Date Issue: 2005
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

Files in This Item:
File Description SizeFormat 
WOS000233883900015.pdf229.29 kBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.