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Towards understanding π-stacking interactions between non-aromatic rings

Molčanov, Krešimir; Kojić-Prodić, Biserka (2019) Towards understanding π-stacking interactions between non-aromatic rings. IUCrJ, 6 (2). pp. 156-166. ISSN 2052-2525

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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 (nonaromatic) 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.

Item Type: Article
Uncontrolled Keywords: π-stacking interactions ; non-aromatic rings ; multicentric bonding ; charge density
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Novi metal-organsi sustavi s oksalatnim i kinoidnim ligandima s podešenim svojstvima pogodnim za primjenu-NMOSBOQLWTPSFPKrešimir MolčanovIP-2014-09-4079HRZZ
Depositing User: Krešimir Molčanov
Date Deposited: 14 Jun 2019 12:41
DOI: 10.1107/S2052252519000186

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