DFT Study on Hydrogen-Bond-Enhanced Aromaticity/Antiaromaticity of the Rings Involved in the pi-Conjugated Hydrogen-Bond System: 3-Hydroxy-2H-benzocyclo(propen and penten)-2-ones and 6-Hydroxy-5H-benzocyclohepten-5-one

摘要

In a C=O center dot center dot center dot HO hydrogen bond incorporated into a pi-conjugation system involving ring structures the hydrogen bond decreases the bond alternation of the system and enhances the aromaticity/antiaromaticity of the involved rings depending on the number of pi-electrons, influencing stability of the system and barrier to proton transfer along the hydrogen bond.