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Supramolecular Architecture of Chloranilate Salts with Organic Cations: pi-stacking vs. Hydrogen Bonding

Molčanov, Krešimir; Androš Dubraja, Lidija; Jurić, Marijana (2019) Supramolecular Architecture of Chloranilate Salts with Organic Cations: pi-stacking vs. Hydrogen Bonding. Croatica Chemica Acta, 92 (2). pp. 297-305. ISSN 0011-1643

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Abstract

Four novel salts of chloranilic acid (H2CA ; 3, 6-dichloro-2, 5-dihydroxy-1, 4-quinone) with organic cations pyridinium (py), piperazinium (ppz), 4, 4'-bipyridinediium (bpy) and 1, 10-phenanthrolinium (phen) were prepared and structurally characterised: (Hpy)2CA (1), (H2ppz)CA (2), (H2bpy)CA·4H2O (3) and (Hphen)HCA·MeOH (4). Supramolecular architecture is based on extensive hydrogen bonding and π-stacking. The central motive is chloranilate dianion which acts as an acceptor of two bifurcated hydrogen bonds. Topology and dimensionality of hydrogen bonded networks can be tuned by use of different cations: thus discrete motives, 1D chains and 2D layers were observed. Three different types of π-stacks are present: aromatic stacks, quinoid stacks and stacks of alternating quinoid and aromatic rings.

Item Type: Article
Uncontrolled Keywords: chloranilic acid ; crystal structure ; crystal engineering ; supramolecular chemistry
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Materials Chemistry
Division of Materials Physics
Projects:
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: 24 Dec 2019 08:09
Last Modified: 12 Aug 2021 14:11
URI: http://fulir.irb.hr/id/eprint/5270
DOI: 10.5562/cca3537

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