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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 & Biomolecular Chemistry, 2004; 2(9):1381-1386
Publisher: Royal Soc Chemistry
Issue Date: 2004
ISSN: 1477-0520
Statement of
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
RMID: 0020040360
DOI: 10.1039/b316450k
Appears in Collections:Chemistry publications
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