Equilibrium Acidities of 2-Alkylthiazolium Cations at the C-2α Position

F. G. Bordwell, A. V. Satish, Frank Jordan, Carlos B. Rios, A. Chitong Chung

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Abstract

The properties of the 2-(1-methoxyethyl)-3,4-dimethylthiazolium cation (3) and seven related thiazolium cations have been investigated as models for the behavior of 2-(1-hydroxyethyl)thiamin (1). The equilibrium acidity (pKHA+) of 3 in Me2SO solution was found to be 14.1 ± 0.05, and evidence is presented to indicate that the value in aqueous solution is within ±1 unit of this value. These values are 3 units, or more, lower than previous estimates for the pKHA+ at C-2α of the thiazolium moiety in 1, which were based on kinetic measurements. Related thiazolium cations, where Me, RO, or Ph groups were introduced into the C-2 side chain, were found to have acidities in the 9-15 pKHA+ range.

Original languageEnglish (US)
Pages (from-to)792-797
Number of pages6
JournalJournal of the American Chemical Society
Volume112
Issue number2
DOIs
StatePublished - Jan 1 1990

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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