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

Yaffa Shalit; Inbal Tuvi-Arad

doi:10.1021/acsomega.1c02684

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

Yaffa Shalit, Inbal Tuvi-Arad

Chemistry

Open University of Israel

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	19233-19237
Number of pages	5
Journal	ACS Omega
Volume	6
Issue number	29
DOIs	https://doi.org/10.1021/acsomega.1c02684
State	Published - 27 Jul 2021

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering

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10.1021/acsomega.1c02684

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title = "Symmetry-Binding Correlations of Crown Ether Complexes with Li+and Na+",

abstract = "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.",

author = "Yaffa Shalit and Inbal Tuvi-Arad",

note = "Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society.",

year = "2021",

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doi = "10.1021/acsomega.1c02684",

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T1 - Symmetry-Binding Correlations of Crown Ether Complexes with Li+and Na+

AU - Shalit, Yaffa

AU - Tuvi-Arad, Inbal

PY - 2021/7/27

Y1 - 2021/7/27

N2 - 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.

AB - 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.

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U2 - 10.1021/acsomega.1c02684

DO - 10.1021/acsomega.1c02684

M3 - مقالة

C2 - 34337261

SN - 2470-1343

VL - 6

SP - 19233

EP - 19237

JO - ACS Omega

JF - ACS Omega

IS - 29

ER -

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

Abstract

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