Open AccessOn the reciprocal relationship between σ-hole bonding and (anti)aromaticity gain in ketocyclopolyenes
Author(s) -
Hari Ram Paudel,
Lucas J. Karas,
Judy I. Wu
Publication year - 2020
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/d0ob01076f
Subject(s) - pnictogen , aromaticity , chemistry , delocalized electron , electron delocalization , antiaromaticity , chalcogen , reciprocal , electron counting , electron , crystallography , molecule , physics , condensed matter physics , organic chemistry , nuclear physics , linguistics , superconductivity , philosophy
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.