Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/17923
Citations | ||
Scopus | Web of ScienceĀ® | Altmetric |
---|---|---|
?
|
?
|
Type: | Journal article |
Title: | Intra- and intermolecular complexation in C(6) monoazacoronand substituted cyclodextrins |
Author: | Lock, J. May, B. Clements, P. Lincoln, S. Easton, C. |
Citation: | Organic and Biomolecular Chemistry, 2004; 2(9):1381-1386 |
Publisher: | Royal Soc Chemistry |
Issue Date: | 2004 |
ISSN: | 1477-0520 1477-0539 |
Statement of Responsibility: | Julia S. Lock, Bruce L. May, Philip Clements, Stephen F. Lincoln and Christopher J. Easton |
Abstract: | The preparation of 6(A)-deoxy-6(A)-(6-(2-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)acetamido)hexylamino)-alpha-cyclodextrin, 3, 6(A)-deoxy-6(A)-(6-(2-(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)acetamido)hexylamino)-alpha-cyclodextrin, 4, and their beta-cyclodextrin analogues, 5 and 6, are described. (1)H (600 MHz) ROESY NMR spectra of the C(6) substituted beta-cyclodextrins, 5 and 6, are consistent with the intramolecular complexation of their azacyclopentadecanyl- and azacyclooctadecanyl(acetamido)hexylamino substituents in the beta-cyclodextrin annulus in D(2)O at pD = 8.5 whereas those of their alpha-cyclodextrin analogues, 3 and 4 are not complexed in the alpha-cyclodextrin annulus. This is attributed to the monoazacoronand components of the substituents being able to pass through the beta-cyclodextrin annulus whereas they are too large to pass through the alpha-cyclodextrin annulus. However, the substituents of 3 and 4 are intermolecularly complexed by beta-cyclodextrin to form pseudo [2]-rotaxanes. Metallocyclodextrins are formed by 5 through complexation by the monoazacoronand substituent component for which log (K/dm(3) mol(-1))= <2, 6.34 and 5.38 for Ca(2+), Zn(2+) and La(3+), respectively, in aqueous solution at 298.2 K and I= 0.10 mol dm(-3)(NEt(4)ClO(4)). |
Keywords: | Azo Compounds Cyclodextrins Molecular Structure Carbohydrate Sequence Molecular Sequence Data |
DOI: | 10.1039/b316450k |
Published version: | http://dx.doi.org/10.1039/b316450k |
Appears in Collections: | Aurora harvest 6 Chemistry publications Environment Institute publications |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.