Issue 27, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
24 may 2020
Accepted
19 iyn 2020
First published
22 iyn 2020

Org. Biomol. Chem., 2020,18, 5125-5129

Author version available

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, 18, 5125 DOI: 10.1039/D0OB01076F

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