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Precision studies in supramolecular chemistry: a 1 H NMR study of hydroxymethoxyacetophenone/β‐cyclodextrin complexes
Author(s) -
Fielding Lee,
McKellar Scott C.,
Florence Alastair J.
Publication year - 2011
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2762
Subject(s) - chemistry , isothermal titration calorimetry , titration , cyclodextrin , supramolecular chemistry , nuclear overhauser effect , nuclear magnetic resonance spectroscopy , proton nmr , calorimetry , two dimensional nuclear magnetic resonance spectroscopy , spectroscopy , fluorine 19 nmr , computational chemistry , analytical chemistry (journal) , molecule , organic chemistry , stereochemistry , thermodynamics , physics , quantum mechanics
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. Copyright © 2011 John Wiley & Sons, Ltd.