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Issue 8, 2019
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Study of through-space substituent–π interactions using N-phenylimide molecular balances

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Abstract

Substituent–π interactions associated with aromatic stacking interactions were experimentally measured using a small N-phenylimide molecular balance model system. The direct interaction of the substituent (NH2, CH3, OH, F, Br, CF3 and NO2) with an aromatic ring was measured in the absence of the aromatic stacking interactions in solution. The measured substituent–π energies were found to correlate well with the Hammett σm parameter similar to the substituent effects observed in aromatic stacking systems. The persistent electrostatic trends in substituent effects can arise from the direct electrostatic interactions between substituents and opposing π-systems.

Graphical abstract: Study of through-space substituent–π interactions using N-phenylimide molecular balances

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Publication details

The article was received on 03 Feb 2019, accepted on 23 Mar 2019 and first published on 25 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00195F
Org. Chem. Front., 2019,6, 1266-1271

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    Study of through-space substituent–π interactions using N-phenylimide molecular balances

    J. Hwang, P. Li, E. C. Vik, I. Karki and K. D. Shimizu, Org. Chem. Front., 2019, 6, 1266
    DOI: 10.1039/C9QO00195F

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