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Inclusion of menadione with cyclodextrins studied by calorimetry and spectroscopic methods
Author(s) -
Zielenkiewicz Wojciech,
Terekhova Irina V.,
Koźbiał Małgorzata,
Poznanski Jaroslaw,
Kumeev Roman S.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1223
Subject(s) - chemistry , isothermal titration calorimetry , menadione , calorimetry , aqueous solution , cyclodextrin , titration , organic chemistry , thermodynamics , enzyme , physics
Abstract Complex formation of menadione with α ‐, hydroxypropyl α ‐, β ‐, hydroxypropyl‐ β ‐, methyl‐ β ‐ and hydroxypropyl‐ γ cyclodextrins in aqueous solution at 298.15 K was studied by using isothermal titration calorimetry, 1 H NMR, and UV–vis spectrophotometry. The experimental data indicated the partial insertion of menadione into macrocyclic cavity upon formation of two alternative types of 1:1 inclusion complexes, whose thermodynamic parameters ( K , Δ c G 0 , Δ c H 0 , and Δ c S 0 ) were calculated. The influence of host size on the complex formation process was analyzed. β ‐Cyclodextrin and its hydroxypropylated and methylated derivatives were found more effective binders towards menadione than α ‐ and γ ‐cyclodextrins. Copyright © 2007 John Wiley & Sons, Ltd.