Ruptured Aromaticity in Nature Chemistry

Our investigation of the interplay between strain and aromatic stabilisation energy has been published in Nature Chemistry.

We use peripheral overcrowding to increment the strain energy around an aromatic cation ring (tropylium). Moderate overcrowding causes the tropylium to twist, but beyond a certain strain energy we found that the aromatic ring ruptures to produce a bicyclic ‘Dewar tropylium’ system. Surprisingly, ramping up the strain energy in this way doesn’t appear to diminsh the aromatic stabilisation energy. Instead, the strain and aromaticity can be balanced so the aromatic and nonaromatic isomers exist in rapid, thermal with one another.

The research was led by PhD student Promeet Saha and PDRA Dr Abhijit Mallick. Congratulations to the whole team!