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

✍ Scribed by Lee Fielding; Scott C. McKellar; Alastair J. Florence

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
219 KB
Volume
49
Category
Article
ISSN
0749-1581

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✦ Synopsis

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. Copyright © 2011 John Wiley & Sons, Ltd.

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