Symmetry-Binding Correlations of Crown Ether Complexes with Li+and Na+

Yaffa Shalit, Inbal Tuvi-Arad

Research output: Contribution to journalArticlepeer-review


The gas-phase structure of 18-crown-6 in the presence of Li+ and Na+ cations is highly flexible and generally distorted. Using density functional theory calculations, natural bond orbital analysis, and symmetry measures, we reveal the driving forces behind the structural and energy trends of 18-crown-6 and its phenyl substituents. We show that the structural deviation from C3-symmetry increases with the non-bonded interactions between the occupied spx orbitals of the crowns' oxygen atoms and the unoccupied 2s orbital of the cation. These orbital interactions are strongly correlated with the overall host-guest interaction energy. Our approach highlights the role of non-bonded interactions and paves the way for deeper understanding of structure-reactivity relations of flexible host-guest systems.

Original languageEnglish
Pages (from-to)19233-19237
Number of pages5
JournalACS Omega
Issue number29
StatePublished - 27 Jul 2021

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© 2021 The Authors. Published by American Chemical Society.


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