Abstract
Diethylaminoethyl (DEAE) groups were introduced into α-cyclodextrin (α-CD) and β-CD. The products, DEAE-CDs with various numbers of substituents, trappedp-nitrophenoxide and 3,4-dinitrophenoxide preferentially over their respective conjugate acids. This caused a decreased pK a of the guest nitrophenol. Some signals of the proton-NMR of both guest nitrophenol and host DEAE-CD changed upon host-guest interaction. The relation between the number of DEAE groups and the extent of the pK a decrease, as well as association constants, is discussed.
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Yagi, T., Aoshima, R., Kuwahara, M. et al. Preferential inclusion of nitrophenoxide ion over its conjugate acid in polycationic cyclodextrin: pK a decrease of nitrophenols by host-guest interaction with diethylaminoethyl-cyclodextrins. J Incl Phenom Macrocycl Chem 16, 231–243 (1993). https://doi.org/10.1007/BF00708793
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DOI: https://doi.org/10.1007/BF00708793