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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 9
BKCSDE 35(9)
September 20, 2014 

Theoretical Study of Trioxane Derivatives as Amphi-ionophores: Importance of Charge-Dipolar Moiety Orientation
Seung Joo Cho
Trioxane, Crown ether, Amphi-ionophore, Charge-dipole, 2n-crown-n
Recently we have reported a novel class of anion receptors which are based on 2n-crown-n topology. Trioxane derivatives are capable of anion sensing through pure aliphatic C-H hydrogen bonding. In this work, we highlight another interesting property, i.e., they can also recognize cations as normal crown ethers (3n-crownn topology). Since the same functional moiety can recognize anions and cations, these coronands are predicted to be amphi-ionophores. However, we could not detect cations even in the gas phase. Considering trioxane is analogous to [16]starand, this was rather counter-intuitive. The calculation results show that these coronands can detect alkali metals with very low affinity. The low affinity toward cations should be responsible for this failure of experimental detection. With careful theoretical study, we found that this low affinity toward cations could be explained by the unfavorable charge-dipolar moiety orientations as proposed by Cui et al. As in the case of [16]starand, this is an example that underscores the importance of charge-dipolar moiety orientation in supramolecular interactions.
2723 - 2725
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