Croatica Chemica Acta, Vol. 92 No. 2, 2019.
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.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.org/0000-0001-5951-9366
; Ruđer Bošković Institute, Bijenička cesta 54, HR-10002, Zagreb, Croatia
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
Publication date:
29.7.2019.
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