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Molecular Recognition Study on a Supramolecular System. Part 21. Inclusion Complexation Thermodynamics of Aliphatic Alcohols by Organoselenium Modified β-Cyclodextrins

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Abstract

The spectrophotometric titrations have beenperformed at 25–40 °C in aqueous solution to give the complexstability constants and the thermodynamic parametersfor the stoichiometric 1 : 1 inclusion complexation ofvarious aliphatic alcohols withmono[6-(phenylseleno)-6-deoxy]-β-cyclodextrin (2),mono[6-(o-, m-,p-tolylseleno)-6-deoxy]-β-cyclodextrin (3–5),mono[6-(p-chloro-phenyl-seleno)-6-deoxy]-β-cyclodextrin(6), mono[6-(benzylseleno)-6-deoxy]-β-cyclodextrin (7) and mono[6-(naphthaleneseleno)-6-deoxy]-β-cyclodextrin(8). On thebasis of the present and previous results, themolecular binding abilities and selectivities forguest aliphatic alcohols of the host β-cyclodextrinderivatives (2–8) are discussed comparatively and globallyfrom the thermodynamic point of view. Thethermodynamic parameters obtained are criticalfunctions of the size/shape of aliphatic alcohols, andthe position and type of the substituent introduced tothe aromatic ring of β-cyclodextrin's sidearm,which are elucidatedin terms of the conformational, electrostatic,hydrogen-bonding, and hydrophobic effects.

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Liu, Y., Li, B., Wada, T. et al. Molecular Recognition Study on a Supramolecular System. Part 21. Inclusion Complexation Thermodynamics of Aliphatic Alcohols by Organoselenium Modified β-Cyclodextrins. Journal of Inclusion Phenomena 36, 311–325 (2000). https://doi.org/10.1023/A:1008147807364

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