Ab initio studies of the effect of the fluorination on deprotonation reaction of the benzene sulfonic acid

Akinori Fukushima, Hironori Sakai, Takashi Tokumasu

研究成果: Article

抜粋

We carried out quantum chemical calculations to analyze the effects of fluorination on the activation energy (Ea) of sulfonic group deprotonation by water molecules. The model molecule was 2,3,4,5,6-pentafluorobenzenesulfonic acid (5FBSA), which was obtained by substituting all aromatic hydrogen atoms of benzenesulfonic acid (BSA) for fluorine atoms. The target hydration level was three. Our analysis indicated that the Ea of deprotonation in 5FBSA was lower than that of BSA, suggesting that the cation of 5FBSA was stabilized. Previous studies have reported that fluorinated molecules have a lower Ea to deprotonation and a stabilized deprotonated state even at a hydration level of three. This effect is attributed to the strong electron withdrawing ability of fluorine. However, compared with non-aromatic molecules, the Ea of deprotonation of aromatic molecules is slightly higher, and the overall energy change (ΔE) is lower, even if the molecule is fluorinated.

元の言語English
記事番号127
ジャーナルJournal of Molecular Modeling
26
発行部数6
DOI
出版物ステータスPublished - 2020 6 1

ASJC Scopus subject areas

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

フィンガープリント Ab initio studies of the effect of the fluorination on deprotonation reaction of the benzene sulfonic acid' の研究トピックを掘り下げます。これらはともに一意のフィンガープリントを構成します。

  • これを引用