Henry Rzepa's Blog Chemistry with a twist

April 18, 2018

Aromaticity-induced basicity.

The molecules below were discussed in the previous post as examples of highly polar but formally neutral molecules, a property induced by aromatisation of up to three rings. Since e.g. compound 3 is known only in its protonated phenolic form, here I take a look at the basicity of the oxygen in these systems to see if deprotonation of the ionic phenol form to the neutral polar form is viable.

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April 9, 2017

Cyclopropenium cyclopentadienide: a strangely neutral ion-pair?

Both the cyclopropenium cation and the cyclopentadienide anion are well-known 4n+2-type aromatic ions, but could the two together form an ion-pair?

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