pH Dependent In−Out Isomerism of an Amino-β-cyclodextrin Derivative
- 20 June 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Physical Chemistry B
- Vol. 110 (27), 13399-13404
- https://doi.org/10.1021/jp061579b
Abstract
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.Keywords
This publication has 54 references indexed in Scilit:
- NMR studies of chiral recognition by cyclodextrinsChirality, 2003
- Determination of second-order association constants by global analysis ofSteroids, 2003
- An NMR study of cyclodextrin complexes of the steroidal neuromuscular blocker drug Rocuronium BromideMagnetic Resonance in Chemistry, 2002
- Dynamic NMR studies of supramolecular complexesProgress in Nuclear Magnetic Resonance Spectroscopy, 2001
- A Practical Guide for the Determination of Binding ConstantsJournal of inclusion phenomena and molecular recognition in chemistry, 2001
- NMR Studies of Cyclodextrins and Cyclodextrin ComplexesChemical Reviews, 1998
- Thermodynamic and Kinetic Data for Macrocycle Interaction with Cations, Anions, and Neutral MoleculesChemical Reviews, 1995
- Crystal structure of 6-O-[(R)-2-hydroxypropyl]cyclomaltoheptaose and 6-O-[(S)-2-hydroxypropyl]cyclomaltoheptaoseCarbohydrate Research, 1993
- NMR Studies of the Structure and Properties of Cyclodextrins and Their Inclusion ComplexesPublished by Elsevier BV ,1993
- Polymeric inclusion compound derived from .beta.-cyclodextrinThe Journal of Organic Chemistry, 1982