Quasi-rings constructed as cyclic β-ketoenol or lithium β-ketoenolate moieties fused to aromatic molecules such as benzene, naphthalene and phenanthrene have geometric consequences for the conjoined aromatic similar to those caused by fusion of a benzene ring. This similarity is particularly marked in the case of lithium-bonded derivatives. Energies of bond separation reactions and the HOMA (harmonic-oscillator model of aromaticity) geometry-based index of π-electron delocalisation show further similarities between quasi-rings and benzene. However, application of the ipsocentric approach to calculation of induced current density, shows that neither hydrogen nor lithium quasi-rings support π-electron ring currents. It is argued that the geometric effects stem from electrostatic interaction of Li+, and to a lesser extent H+, with oxygen neighbours, causing a partial equalisation of CO bond lengths and knock-on effects on CC bonds, in the quasi-ring. The observed geometric effects do not arise from aromatic π-electron delocalisation in the quasi-ring but are closer to the well-known push–pull effect between the electron-donating –OH and electron-accepting –CO groups, leading to reduction in bond-length alternation.
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