Towards understanding π-stacking interactions between non-Aromatic rings

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Abstract

The first systematic study of π interactions between non-Aromatic rings, based on the authors' own results from an experimental X-ray charge-density analysis assisted by quantum chemical calculations, is presented. The landmark (non-Aromatic) examples include quinoid rings, planar radicals and metal-chelate rings. The results can be summarized as: (i) non-Aromatic planar polyenic rings can be stacked, (ii) interactions are more pronounced between systems or rings with little or no π-electron delocalization (e.g. quinones) than those involving delocalized systems (e.g. aromatics), and (iii) the main component of the interaction is electrostatic/multipolar between closed-shell rings, whereas (iv) interactions between radicals involve a significant covalent contribution (multicentric bonding). Thus, stacking covers a wide range of interactions and energies, ranging from weak dispersion to unlocalized two-electron multicentric covalent bonding ('pancake bonding'), allowing a face-To-face stacking arrangement in some chemical species (quinone anions). The predominant interaction in a particular stacked system modulates the physical properties and defines a strategy for crystal engineering of functional materials.

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Molcanov, K., & Kojić-Prodić, B. (2019). Towards understanding π-stacking interactions between non-Aromatic rings. IUCrJ. International Union of Crystallography. https://doi.org/10.1107/S2052252519000186

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