Nucleophilic and electrophilic radical attack on maleic and fumaric acids in aqueous solution

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Abstract

Rate coefficients (k) of {radical dot}CH2OH, CH3{radical dot} CHOH, (CH3)2{radical dot} COH and Cl2- {radical dot} radical addition to maleic and fumaric acids were investigated between pH 1 and 8. Strong pH dependences observed were attributed to changes in protonation states of acids: H2X, HX- and X2-. k of {radical dot}CH2OH, CH3{radical dot} CHOH, (CH3)2{radical dot} COH addition to fumaric acid decreased in the order kH2 F > kHF- > kF2 - in agreement with the nucleophilic character of reaction. The electrophilic Cl2- {radical dot} radical showed opposite tendency. With maleic acid the monoanion had the highest reactivity towards nucleophilic and the lowest one towards electrophilic radicals. This is attributed to a prevalence of steric over polar effects for HM-.

Original languageEnglish
Pages (from-to)451-456
Number of pages6
JournalChemical Physics Letters
Volume460
Issue number4-6
DOIs
Publication statusPublished - Jul 30 2008

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ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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