Calorimetric investigation of guanidinium-carboxylate interactions

Brian Linton, Andrew Hamilton

Research output: Contribution to journalArticle

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

Fingerprint

Calorimetry
Guanidine
Acetates
Association reactions
Derivatives
Hydrogen Bonding
Dimethyl Sulfoxide
Thermodynamics
Hydrogen
Hydrogen bonds
Titration
Stoichiometry
Experiments
tetrabutylammonium

Keywords

  • Calorimetry
  • Carboxylate
  • Guanidinium
  • Molecular recognition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Calorimetric investigation of guanidinium-carboxylate interactions. / Linton, Brian; Hamilton, Andrew.

In: Tetrahedron, Vol. 55, No. 19, 07.05.1999, p. 6027-6038.

Research output: Contribution to journalArticle

@article{f697710ebb3d4f2e99bc24143fc9dcb7,
title = "Calorimetric investigation of guanidinium-carboxylate interactions",
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.",
keywords = "Calorimetry, Carboxylate, Guanidinium, Molecular recognition",
author = "Brian Linton and Andrew Hamilton",
year = "1999",
month = "5",
day = "7",
doi = "10.1016/S0040-4020(99)00277-X",
language = "English (US)",
volume = "55",
pages = "6027--6038",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "19",

}

TY - JOUR

T1 - Calorimetric investigation of guanidinium-carboxylate interactions

AU - Linton, Brian

AU - Hamilton, Andrew

PY - 1999/5/7

Y1 - 1999/5/7

N2 - 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.

AB - 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.

KW - Calorimetry

KW - Carboxylate

KW - Guanidinium

KW - Molecular recognition

UR - http://www.scopus.com/inward/record.url?scp=0033532094&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033532094&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00277-X

DO - 10.1016/S0040-4020(99)00277-X

M3 - Article

AN - SCOPUS:0033532094

VL - 55

SP - 6027

EP - 6038

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 19

ER -