Yes. Aromatic rings are not required for molecules to stack, and some studied non-aromatic systems show more pronounced interactions than aromatic ones. But that is a finding about particular molecular systems—not a rule that removing aromaticity makes stacking stronger. The answer depends on the partners, their geometry, and the surrounding chemical environment.
What does “better” mean in pi-stacking?
“Pi-stacking” is a broad name for arrangements in which molecular rings or other pi systems lie over or near one another. It does not identify one universal force, and aromaticity is neither a prerequisite for a stacking arrangement nor a reliable predictor of its strength on its own.
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A 2019 review by Krešimir Molčanov and Biserka Kojić-Prodić describes non-aromatic planar polyenic rings—including quinones, radicals, and metal-chelate rings—that stack. In some of the examples reviewed, interactions between systems with little or no pi-electron delocalization are more pronounced than those involving delocalized aromatic systems. That comparison applies to the studied systems, not to every non-aromatic and aromatic pair.
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Repair common Windows errors and clear accumulated junk for a smoother, more stable PC - no reinstall needed.Free scan · no reinstallWhy can non-aromatic rings interact strongly?
The physical contributions differ by system. For the closed-shell non-aromatic rings discussed in the review, the interaction is described mainly in electrostatic or multipolar terms. The rings’ charge patterns and electrostatic potentials matter; the mere presence or absence of aromaticity does not settle the comparison.
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Radical stacks are a different case: the review describes a significant covalent, multicentric contribution, sometimes called “pancake bonding.” So a short inter-ring distance—or the broad label “pi-stacking”—does not by itself reveal the interaction mechanism or establish its strength. The review interprets structures using X-ray charge-density analysis supported by quantum-chemical calculations.
What the hydrogen chloranilate example does—and does not—show
For stacked hydrogen chloranilate rings in potassium hydrogen chloranilate dihydrate, Molčanov and Kojić-Prodić report an estimated interaction energy near −10 kcal mol−1. That estimate is specific to this crystal example: it draws on isolated-cluster MP2 calculations and periodic DFT, and the review notes that lattice effects, including charge compensation by nearby cations, are relevant.
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It should not be treated as a typical energy for non-aromatic stacking or as a universal head-to-head comparison with aromatic dimers. A meaningful strength comparison needs to specify the molecules, charge states, geometry, phase, environment, and method used to estimate or interpret the interaction.
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- Identify the partners: distinguish aromatic from non-aromatic rings, and closed-shell from radical or charged species.
- Check the arrangement: face-to-face and offset geometries need not have the same interaction.
- Account for the setting: an isolated pair is not equivalent to molecules in a crystal lattice or a solvent and ionic environment.
- Ask what “strength” measures: a structural distance alone is not an energy or a complete account of the mechanism; note the analysis or calculation behind the comparison.
Because authors use “stacking” terminology in different ways, it is clearer to name the molecular partners, geometry, and proposed physical contributions than to imply that every case is governed by one distinct “pi force.”
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