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Theoretical Study of Trioxane Derivatives as Amphi-ionophores: Importance of Charge-Dipolar Moiety Orientation
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  • Theoretical Study of Trioxane Derivatives as Amphi-ionophores: Importance of Charge-Dipolar Moiety Orientation
  • Theoretical Study of Trioxane Derivatives as Amphi-ionophores: Importance of Charge-Dipolar Moiety Orientation
저자명
Cho. Seung Joo
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2014년|35권 9호|pp.2723-2725 (3 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
서지반출

기타언어초록

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-crown-n 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 [$1_6$]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 [$1_6$]starand, this is an example that underscores the importance of charge-dipolar moiety orientation in supramolecular interactions.