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

L. Wojnárovits, E. Takács, Salvatore S. Emmi

Research output: Contribution to journalArticle

2 Citations (Scopus)

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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attack
aqueous solutions
acids
Protonation
Acids
maleic acid
fumaric acid
tendencies
reactivity
coefficients

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Surfaces and Interfaces
  • Condensed Matter Physics

Cite this

Nucleophilic and electrophilic radical attack on maleic and fumaric acids in aqueous solution. / Wojnárovits, L.; Takács, E.; Emmi, Salvatore S.

In: Chemical Physics Letters, Vol. 460, No. 4-6, 30.07.2008, p. 451-456.

Research output: Contribution to journalArticle

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AB - 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-.

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