Skip to the main content

Original scientific paper

https://doi.org/10.5562/cca3537

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

Krešimir Molčanov orcid id orcid.org/0000-0002-4328-3181 ; Ruđer Bošković Institute, Bijenička cesta 54, HR-10002, Zagreb, Croatia
Lidija Androš Dubraja ; Ruđer Bošković Institute, Bijenička cesta 54, HR-10002, Zagreb, Croatia
Marijana Jurić orcid id orcid.org/0000-0001-5951-9366 ; Ruđer Bošković Institute, Bijenička cesta 54, HR-10002, Zagreb, Croatia


Full text: english pdf 11.964 Kb

page 297-305

downloads: 445

cite


Abstract

Four novel salts of chloranilic acid (H2CA; 3,6-dichloro-2,5-dihydroxy-1,4-quinone) with organic cations pyridinium (Hpy+), piperazinediium (H2ppz2+), 4,4'-bipyridinediium (H2bpy2+) and 1,10-phenanthrolinium (Hphen+) 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.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

chloranilic acid, crystal structure, crystal engineering, supramolecular chemistry

Hrčak ID:

228429

URI

https://hrcak.srce.hr/228429

Visits: 882 *