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

The title salt, K(+)·C(6)H(7)O(9)S(−)·2H(2)O, 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...

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Autores principales: Haines, Alan H., Hughes, David L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588254/
https://www.ncbi.nlm.nih.gov/pubmed/23476359
http://dx.doi.org/10.1107/S1600536812048672
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author Haines, Alan H.
Hughes, David L.
author_facet Haines, Alan H.
Hughes, David L.
author_sort Haines, Alan H.
collection PubMed
description The title salt, K(+)·C(6)H(7)O(9)S(−)·2H(2)O, 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.
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spelling pubmed-35882542013-03-08 Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate Haines, Alan H. Hughes, David L. Acta Crystallogr Sect E Struct Rep Online Metal-Organic Papers The title salt, K(+)·C(6)H(7)O(9)S(−)·2H(2)O, 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. International Union of Crystallography 2012-12-05 /pmc/articles/PMC3588254/ /pubmed/23476359 http://dx.doi.org/10.1107/S1600536812048672 Text en © Haines and Hughes 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Metal-Organic Papers
Haines, Alan H.
Hughes, David L.
Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title_full Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title_fullStr Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title_full_unstemmed Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title_short Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
title_sort potassium (1r,4r,5s,8s)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate
topic Metal-Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588254/
https://www.ncbi.nlm.nih.gov/pubmed/23476359
http://dx.doi.org/10.1107/S1600536812048672
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