On the extension of the Hückel rule to polycyclic non-alternant conjugated hydrocarbons

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Abstract
General rules for aromatic stability of non-alternant polycyclic conjugated hydrocarbons are obtained using graph–theoretical considerations. Every pair of odd-membered rings contained in the conjugated molecule has a stabilizing effect if one ring is of the size 4N + 1 and the other of the size 4N + 3. If both rings are of the size 4N + 1 or 4N + 3, a destabilizing effect occurs. This conclusion holds both for fused and disjointed rings. The π-electron System is said to be relatively more stable if the number of (4N + l)-membered rings is equal to the number of (4N + 3)-rings.

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