A single aqueous reference equilibrium constant for amide synthesis-hydrolysis

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29 Citations (Scopus)

Abstract

Experimentally measured equilibrium constants at a given pH in part reflect the contributions of ionisation of acidic and basic groups present. These contributions can be isolated from the equilibrium constant by expressing all reactant concentrations in terms of the uncharged forms only. This article presents methods to calculate uncharged reference equilibrium constants for amide synthesis/hydrolysis reactions. For zwitterions in particular these methods are not always straightforward. It is explained how (microscopic) pK(a) values can be estimated where experimental values are not available. A large number of equilibrium data are analysed for hydrolysis or synthesis of protected and unprotected di- and tri-peptides, beta-lactam antibiotics, and acyl acids and amides. This reveals just how similar the reference equilibrium constants are when ionisation is properly accounted for (K-ref(0) = 10(3.6) M-1) regardless of the molecular form of the reactants involved.
Original languageEnglish
Pages (from-to)1024-1028
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Volume2002
Issue number5
DOIs
Publication statusPublished - 2002

Keywords

  • Thermodynamically controlled synthesis
  • beta-lactam antibiotics
  • peptide-synthesis
  • amoxicillin
  • thermolysin
  • protease
  • systems
  • salts

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