Potassium (1R,4R,5S,8S)-4,5,8-trihydroxy-3-oxo-2,6-dioxabicyclo[3.3.0]octane-4-sulfonate dihydrate

Haines, Alan H. and Hughes, David L. (2013) Potassium (1R,4R,5S,8S)-4,5,8-trihydroxy-3-oxo-2,6-dioxabicyclo[3.3.0]octane-4-sulfonate dihydrate. Acta Crystallographica Section E: Structure Reports Online, 69 (1). m7-m8. ISSN 1600-5368

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Abstract

The title salt, K+·C6H7O9S-·2H2O, formed by reaction of dehydro-L-ascorbic acid with potassium hydrogen sulfite in water, crystallizes as colourless plates. The potassium ion is coordinated by eight O atoms arising from hydroxy or sulfonate groups. The sulfonate group is bonded to the C atom neighbouring that of the lactone carbonyl group. As is commonly observed in crystalline L-ascorbic acid derivatives, the O atom of the primary hydroxy group is linked to the second C atom from the lactone C atom, forming a hemi-acetal function, thereby creating a bicyclic system of two fused five-membered rings, both of which have envelope conformations with one of the shared C atoms as the flap. Addition of the sulfur nucleophile occurs from the less hindered face. One of the two independent lattice water molecules has hydrogen bonds to sulfonate O atoms of two different anions and is the acceptor of bonds from hydroxy groups of two further anions; the second lattice water molecule donates to the carbonyl and a hydroxy O atom in different anions, and accepts from a hydroxy O atom in a further anion. Thus, through K-O coordination and hydrogen bonds, the potassium cations, sulfonate anions and water molecules are linked in a three-dimensional network.

Item Type: Article
Additional Information: Published in an open access journal with a licence identical to a Creative Commons Attribution Licence; see http://journals.iucr.org/e/journalhomepage.html.
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 27 Aug 2014 13:36
Last Modified: 21 Apr 2020 23:23
URI: https://ueaeprints.uea.ac.uk/id/eprint/49992
DOI: 10.1107/S1600536812048672

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