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Published on: June 21, 2017
Binding of substituted acetic acids to alpha-cyclodextrin in aqueous solution
1School of Pharmacy, University of Wisconsin, Madison 53706, USA.
This study quantifies binding constants for aliphatic acids and alpha-cyclodextrin, revealing that acids form stronger complexes than bases. Hydrophobic effects and dispersion interactions drive complex stability.
Area of Science:
- Supramolecular Chemistry
- Physical Organic Chemistry
Background:
- Cyclodextrins are widely used host molecules in various applications.
- Understanding host-guest complexation is crucial for designing new materials and processes.
Purpose of the Study:
- To determine the binding constants of 23 aliphatic acids with alpha-cyclodextrin.
- To investigate the factors influencing the stability of these inclusion complexes.
Main Methods:
- Potentiometry
- Solubility measurements
- Competitive spectrophotometry
Main Results:
- All systems formed 1:1 acid:cyclodextrin complexes; some also formed 1:2 complexes.
- Conjugate acids generally exhibited stronger binding than conjugate bases.
- Complex stability correlated with descriptors like partition coefficients and surface area.
Conclusions:
- The binding of aliphatic acids to alpha-cyclodextrin is influenced by the acid's properties.
- Hydrophobic effects, dispersion interactions, and carboxylic acid group interactions are key drivers of complex stability.
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The α0 and α1 values represent the...

