Thermodynamic insight into the origin of the inclusion of monosulfonated isomers of triphenylphosphine into the β-cyclodextrin cavity

Formation of inclusion complexes between the β-cyclodextrin and the potassium salt of o-, m-, and p-substituted monosulfonated triphenylphosphine derivatives was investigated in aqueous solution by NMR spectroscopy. Titration and continuous variation plots obtained from 31P and 1H NMR data indicate...

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Bibliographic Details
Published in:Carbohydrate research 2002-02, Vol.337 (3), p.281-287
Main Authors: Canipelle, Michaël, Caron, Laurent, Christine, Caline, Tilloy, Sébastien, Monflier, Eric
Format: Article
Language:English
Subjects:
beta-Cyclodextrins
Catalysis
Chemical Sciences
Cyclodextrins - chemistry
Enthalpy
Entropy
Inclusion complex
Isomerism
Magnetic Resonance Spectroscopy - methods
Monosulfonated triphenylphosphine
NMR spectroscopy
Organic chemistry
Organophosphorus Compounds - chemistry
Thermodynamics
β-Cyclodextrin
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Summary:Formation of inclusion complexes between the β-cyclodextrin and the potassium salt of o-, m-, and p-substituted monosulfonated triphenylphosphine derivatives was investigated in aqueous solution by NMR spectroscopy. Titration and continuous variation plots obtained from 31P and 1H NMR data indicate the formation of a 1:1 inclusion complex for the three phosphine isomers. T-ROESY NMR experiments show that in all cases a non-sulfonated aromatic ring was included into the hydrophobic cavity of β-cyclodextrin from the secondary hydroxyl groups side. The standard enthalpy and entropy of the inclusion process were estimated from the temperature dependence of the association constant. All inclusion complexes were enthalpy stabilized, but highly entropy destabilized. The o-, m-, and p-substituted monosulfonated triphenylphosphines form 1:1 inclusion complexes with β-cyclodextrin. All inclusion complexes were enthalpy stabilized, but entropy destabilized.
ISSN:0008-6215
1873-426X
0008-6215
DOI:10.1016/S0008-6215(01)00308-1