Study of through-space substituent–π interactions using N-phenylimide molecular balances
Literature Information
Publication Date
2019-03-25
DOI
10.1039/C9QO00195F
Impact Factor
5.281
Authors
Jungwun Hwang, Ping Li, Erik C. Vik, Ishwor Karki, Ken D. Shimizu
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
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