Precision studies in supramolecular chemistry: a 1H NMR study of hydroxymethoxyacetophenone/β-cyclodextrin complexes

Lee Fielding, Scott C McKellar, Alastair J Florence

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The association constants for the interactions of 2-hydroxy-4-methoxyacetophenone, 2-hydroxy-5-methoxyacetophenone, 2-hydroxy-6-methoxyacetophenone, 3-hydroxy-4-methoxyacetophenone and 4-hydroxy-3-methoxyacetophenone with β-cyclodextrin in water were measured by (1)H NMR and by isothermal titration calorimetry. Very good agreement was obtained between the different methods. The errors associated with the NMR method for measuring mM binding affinities were estimated to be 10-30%, and by isothermal titration calorimetry, 10-20%. Rotating frame nuclear Overhauser effect spectroscopy studies show that the solution phase host-guest complexes formed by β-cyclodextrin with these hydroxymethoxyacetophenone derivatives are not structurally well defined but that the hydroxymethoxyacetophenone derivatives are mostly associated with the narrow primary hydroxyl rim.
LanguageEnglish
Pages405-412
Number of pages8
JournalMagnetic Resonance in Chemistry
Volume49
Issue number7
DOIs
Publication statusPublished - Jul 2011

Fingerprint

Supramolecular chemistry
Cyclodextrins
Calorimetry
Titration
Nuclear magnetic resonance
Derivatives
Hydroxyl Radical
Association reactions
Spectroscopy
Hydrogen
Water
betadex

Keywords

  • NMR
  • 1H NMR
  • 13C NMR
  • cyclodextrin
  • hydroxymethoxyacetophenones
  • stability constants

Cite this

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title = "Precision studies in supramolecular chemistry: a 1H NMR study of hydroxymethoxyacetophenone/β-cyclodextrin complexes",
abstract = "The association constants for the interactions of 2-hydroxy-4-methoxyacetophenone, 2-hydroxy-5-methoxyacetophenone, 2-hydroxy-6-methoxyacetophenone, 3-hydroxy-4-methoxyacetophenone and 4-hydroxy-3-methoxyacetophenone with β-cyclodextrin in water were measured by (1)H NMR and by isothermal titration calorimetry. Very good agreement was obtained between the different methods. The errors associated with the NMR method for measuring mM binding affinities were estimated to be 10-30{\%}, and by isothermal titration calorimetry, 10-20{\%}. Rotating frame nuclear Overhauser effect spectroscopy studies show that the solution phase host-guest complexes formed by β-cyclodextrin with these hydroxymethoxyacetophenone derivatives are not structurally well defined but that the hydroxymethoxyacetophenone derivatives are mostly associated with the narrow primary hydroxyl rim.",
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Precision studies in supramolecular chemistry : a 1H NMR study of hydroxymethoxyacetophenone/β-cyclodextrin complexes. / Fielding, Lee; McKellar, Scott C; Florence, Alastair J.

In: Magnetic Resonance in Chemistry , Vol. 49, No. 7, 07.2011, p. 405-412.

Research output: Contribution to journalArticle

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