Remarkable selectivity of per-O-methylated tricationic 6A,6C,6E-tripyridinio-6A,6C,6E-trideoxy-α-cyclodextrin for basic anions over non-basic anions

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説明

The per-O-methylated tricationic 6A,6C,6E-tripyridinio-6A,6C,6E-trideoxy-α-cyclodextrin shows a high affinity for basic anions, especially highly charged phosphate and pyrophosphate anions, at near-neutral pH with association constants of 7 000 and 9 000 M−1, respectively, but it did not bind non-basic anions, such as I−, ClO4−, SCN− or even doubly charged SO42−, in contrast to the non-methylated counterpart. 1H NMR spectral studies verify a plausible structure, in which the bound anion is located more closely to the pyridinio meta and para positions rather than to the ortho positions, due probably to the greater MeO- vs. HO-group hydrophobicity, which rejects deep intrusion of the anion into the positive cavity. Molecular mechanics calculations supported the above conclusions.

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詳細情報 詳細情報について

  • CRID
    1872835442387320960
  • DOI
    10.1039/b101042p
  • ISSN
    13645471
    1472779X
  • データソース種別
    • OpenAIRE

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