Unique Electronic and Structural Properties of 1,4-Benzoquinones: Crystallochemistry of Alkali Chloranilate Hydrates

Molčanov, Krešimir; Kojić-Prodić, Biserka; Meden, Anton (2009) Unique Electronic and Structural Properties of 1,4-Benzoquinones: Crystallochemistry of Alkali Chloranilate Hydrates. Croatica Chemica Acta, 82 (2). pp. 387-396. ISSN 0011-1643

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Abstract

The unique electronic and structural characteristics of 1,4-beilzoquinones with possibilities for numerous interactions such as coordination, hydrogen bonding accompanied by proton and/or electron transfer, pi-interactions, and redox activity, are used by nature to perform important biological reactions. In spite of their wide use in supramolecular chemistry for construction of functional materials, the intercorrelation of their versatile interactions has not been completely evaluated. The impacts of hydrogen bonding and cations on interactions of quinoid skeleton are studied on the prepared series of alkali (Li(+), Na(+), K(+), NH(4)(+), and Rb(+)) chloranilate hydrates, and anhydrous caesium homologue. The pi center dot center dot center dot pi stacking interactions of chloranilate dianions observed in the structures of sodium chloranilate dihydrate and caesium sodium chloranilate monohydrate [with centroid separation distances of 3.662(1) and 3.740(2) angstrom and shifts of 1.698 and 1.358 angstrom. respectively] are tuned by hydrogen bonding involving water Molecules. The crystal structures of potassium and rubidium chloranilate monohydrates are isostructural whereas their ammonium homologue, due to the presence of cation with pronounced proton-donor activity, exhibits completely different hydrogen bonding network. In the six of seven structures studied chloranilate dianion reveals the crystallographic symmetry C(i).

Item Type:	Article
Uncontrolled Keywords:	1,4-benzoquinones; chloranilic acid and derivatives; electronic properties; structural properties; hydrogen bonds; pi-stacking; crystallochemistry of alkali chloranilate hydrates; porous coordination polymers; crystal-structure; hydrogen-bond; acid; quinones; complex; mode
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Protein-ligand međudjelovanja na atomnoj razini [77430] Marija Luić 098-1191344-2943 MZOS
Depositing User:	Biserka Kojić-Prodić
Date Deposited:	18 Oct 2013 08:25
URI:	http://fulir.irb.hr/id/eprint/811

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