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Yes: aromatic rings are not required for stacking, and some studied non-aromatic systems show more pronounced interactions than aromatic systems. But that is a result for particular molecules and conditions—not a rule that removing aromaticity makes stacking stronger. “Pi-stacking” describes a range of arrangements and interactions, not one universal force.
What does “better” mean in pi-stacking?
The question can mean two different things: whether rings can stack without being aromatic, and whether a particular non-aromatic stack interacts more strongly than an aromatic one. The answer to the first is yes. For the second, a 2019 review by Krešimir Molčanov and Biserka Kojić-Prodić reports more pronounced interactions in some low-delocalization systems, including quinones, than in the delocalized aromatic systems considered. That comparison applies to the studied examples, not to every pair of molecules.
Aromaticity and stacking are distinct ideas. Aromaticity concerns electron delocalization within a ring; stacking describes how molecular partners are arranged relative to one another. The review discusses non-aromatic planar polyenic rings, including quinones, radicals, and metal-chelate rings, that can form stacked arrangements. Molčanov and Kojić-Prodić’s 2019 review frames the result in terms of the specific systems and their interactions.
Why can non-aromatic rings interact strongly?
There is no single mechanism that explains every stack. The review distinguishes closed-shell rings from radical systems: interactions between the closed-shell rings it discusses are mainly electrostatic and multipolar, while radical stacks can include a significant covalent, multicentric contribution, often called “pancake bonding.” The charge distribution and electronic state of the partners therefore matter, not just whether a ring is aromatic.
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- Closed-shell partners: electrostatic and multipolar contributions are central in the reviewed examples.
- Radical partners: a significant covalent contribution may be present in addition to other interactions.
Because the mechanism varies, “pi-stacking” should not be treated as the name of one unique force. The review notes that the terminology itself varies among authors; describing the partners, geometry, and proposed contributions is more informative than relying on the label alone.
What does the hydrogen chloranilate example show?
For stacked hydrogen chloranilate rings in potassium hydrogen chloranilate dihydrate, the review reports an estimated interaction energy near −10 kcal mol−1. The estimate comes from isolated-cluster MP2 calculations and periodic DFT. It belongs to that particular crystal context, where lattice effects—including charge compensation by nearby cations—are relevant. It is not a generic energy for non-aromatic stacking or a universal head-to-head comparison with aromatic dimers.
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This example illustrates why a strength claim needs its context: the molecular partners, charge state, geometry, surrounding crystal, and computational method all inform what the reported energy means.
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A structure with closely spaced rings shows an arrangement, but distance alone does not establish the interaction’s strength or mechanism. Molčanov and Kojić-Prodić interpret structures using X-ray charge-density analysis supported by quantum-chemical calculations. Those approaches help distinguish electrostatic or multipolar contributions from covalent contributions; a measured separation by itself cannot do that.
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Any comparison between aromatic and non-aromatic stacks is most useful when it states whether the partners are closed-shell, radical, or charged; how their charge is distributed; whether the geometry is face-to-face or offset; and whether the result concerns an isolated pair or a crystal environment. Without those details, “stronger” can conceal comparisons between unlike systems.
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