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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3588254 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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