| Name | Structure | Notes | |------|-----------|-------| | | C₆H₇⁺ | The simplest; protonated benzene. | | Naphthalenium | C₁₀H₉⁺ | Protonated naphthalene; can form at two different positions (1- or 2-naphthalenium). | | Tropylium | C₇H₇⁺ | The exception! This is stable and aromatic (7 π-electrons, Hückel’s rule). Often compared/contrasted with aronium. | | Protonated arenes | Various | Any aromatic compound with an extra H⁺ on a ring carbon. |
The classic example is the (C₆H₇⁺). Imagine a benzene ring (C₆H₆). Normally, it has three double bonds in perfect resonance. Now, add one extra proton (H⁺) to one of the carbon atoms. That carbon goes from being sp² -hybridized (trigonal, part of a double bond) to sp³ -hybridized (tetrahedral, single bonds only). aronium
The result? The beautiful, stable, aromatic ring is temporarily broken. The positive charge is no longer delocalized over six carbons; it’s localized on the sp³ carbon and its neighbors. | Name | Structure | Notes | |------|-----------|-------|