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Title: Study of through-space substituent–π interactions using N -phenylimide molecular balances
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 (NH 2 , CH 3 , OH, F, Br, CF 3 and NO 2 ) 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 σ m 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.  more » « less
Award ID(s):
1709086
PAR ID:
10106766
Author(s) / Creator(s):
; ; ; ;
Date Published:
Journal Name:
Organic Chemistry Frontiers
Volume:
6
Issue:
8
ISSN:
2052-4129
Page Range / eLocation ID:
1266 to 1271
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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