Issue 8, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
03 Kol 2019
Accepted
23 Ube 2019
First published
25 Ube 2019

Org. Chem. Front., 2019,6, 1266-1271

Author version available

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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