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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Electron impact studies. CXXII. A comparison of reactivities and decompositions of benzoate anions and cations

JH Bowie and PY White

Australian Journal of Chemistry 31(7) 1511 - 1517
Published: 1978

Abstract

The benzoate anion reacts with acetic anhydride to yield an intermediate which decomposes by loss of ketene with accompanying proton transfer. The proton transfer is involved in the rate- determining step of the elimination reaction. The abundance of the product ion in the reaction of RC6H4CO2- with acetic anhydride increases as the electron-donating properties of R increase.    

Collision-induced charge stripping of the ions RC6H4CO2- yields the corresponding cations which fragment primarily by elimination of CO2 (or O+CO). Fragmentation through the carboxyl centre precedes the fragmentation of R (e.g. when R = Me, MeO, Cl or Br).

https://doi.org/10.1071/CH9781511

© CSIRO 1978

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