pH Dependent In−Out Isomerism of an Amino-β-cyclodextrin Derivative

An amino derivative of β-cyclodextrin [6-(6-aminehexanamide)-6-deoxy)-β-cyclodextrin (6-βCD)] was synthesized, and the formation of an intramolecular inclusion complex was studied by NMR techniques. The deprotonation/protonation of the amino group stimulates an in/out movement of the pendant group t...

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Veröffentlicht in:	The journal of physical chemistry. B 2006-07, Vol.110 (27), p.13399-13404
Hauptverfasser:	Alcalde, Mercedes Alvarez, Gancedo, Cristina, Jover, Aida, Carrazana, Jorge, Soto, Victor H, Meijide, Francisco, Tato, José Vázquez
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container_issue	27
container_start_page	13399
container_title	The journal of physical chemistry. B
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creator	Alcalde, Mercedes Alvarez Gancedo, Cristina Jover, Aida Carrazana, Jorge Soto, Victor H Meijide, Francisco Tato, José Vázquez
description	An amino derivative of β-cyclodextrin [6-(6-aminehexanamide)-6-deoxy)-β-cyclodextrin (6-βCD)] was synthesized, and the formation of an intramolecular inclusion complex was studied by NMR techniques. The deprotonation/protonation of the amino group stimulates an in/out movement of the pendant group toward/from the cyclodextrin cavity, the protonated species lying outside the hydrophobic cyclodextrin cavity but the unprotonated one residing inside and outside the cavity. The protonation of the amino group is a fast exchange rate NMR time-scale process, but the chain movement is a slow one. The equilibrium constants of both processes were determined from 1H NMR experiments and the kinetic constants for the slow process were determined from exchange spectroscopy (EXSY) experiments.
doi_str_mv	10.1021/jp061579b
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title	pH Dependent In−Out Isomerism of an Amino-β-cyclodextrin Derivative
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