Calorimetric investigation of guanidinium-carboxylate interactions

Brian Linton, Andrew D. Hamilton

Research output: Contribution to journalArticlepeer-review

Abstract

Isothermal titration calorimetry was utilized to study the association between a series of guanidinium derivatives and tetrabutylammonium acetate. This technique provides a measure of association strength, stoichiometry of binding, as well as thermodynamic parameters of association from a single experiment. Guanidinium derivatives which can form bidentate linear hydrogen bonds with acetate show significant, exothermic binding in DMSO (Ka = 5600 M-1; ΔH = -3.6 kcal/mol), while derivatives which lack this bidentate linear hydrogen bonding interaction result in complexes where association is weaker (Ka ≃ 100 M-1) and enthalpically neutral or endothermic. Additionally calorimetry permits the complete assessment of the multiple binding equilibria when derivatives complex two equivalents of guest.

Original languageEnglish (US)
Pages (from-to)6027-6038
Number of pages12
JournalTetrahedron
Volume55
Issue number19
DOIs
StatePublished - May 7 1999

Keywords

  • Calorimetry
  • Carboxylate
  • Guanidinium
  • Molecular recognition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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