Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



On the reciprocal relationship between σ-hole bonding and (anti)aromaticity gain in ketocyclopolyenes

Author affiliations

Abstract

σ-Hole bonding interactions (e.g., tetrel, pnictogen, chalcogen, and halogen bonding) can polarize π-electrons to enhance cyclic [4n] π-electron delocalization (i.e., antiaromaticity gain) or cyclic [4n + 2] π-electron delocalization (i.e., aromaticity gain). Examples based on the ketocyclopolyenes: cyclopentadienone, tropone, and planar cyclononatetraenone are presented. Recognizing this relationship has implications, for example, for tuning the electronic properties of fulvene-based π-conjugated systems such as 9-fluorenone.

Graphical abstract: On the reciprocal relationship between σ-hole bonding and (anti)aromaticity gain in ketocyclopolyenes

Back to tab navigation

Supplementary files

Article information


Submitted
24 May 2020
Accepted
19 Jun 2020
First published
22 Jun 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

On the reciprocal relationship between σ-hole bonding and (anti)aromaticity gain in ketocyclopolyenes

H. R. Paudel, L. J. Karas and J. I. Wu, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01076F

Social activity

Search articles by author

Spotlight

Advertisements