H. Dodziuk et al., A dynamic NMR study of self-inclusion of a pendant group in amphiphilic 6-thiophenyl-6-deoxycyclodextrins, J MOL STRUC, 519, 2000, pp. 33-36
The dynamic stereochemistry of amphiphilic derivatives of alpha-, beta-, an
d gamma-cyclodextrins (1-3) has been investigated by means of variable temp
erature H-1 and C-13 NMR spectroscopy in DMF-d(7) solutions. The most signi
ficant spectral changes were detected for the smallest hexakis(6-thiophenyl
-6-deoxy)-alpha-cyclodextrin (1) and they decrease with the increase of the
macrocycle size. On the basis of ROESY measurements, these changes reflect
ing restricted movements of thiophenyl groups upon the temperature decrease
were interpreted in terms of self-inclusion of at least one thiophenyl gro
up. Molecular modeling of these compounds is consistent with these findings
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