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

Hari Ram Paudel | Zendy; Lucas J. Karas | Zendy; Judy I. Wu | Zendy

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On 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.

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