Crystal structure of potassium (1S)-d-lyxit-1-yl-sulfonate monohydrate.

Alan H Haines,David L Hughes

doi:10.1107/s2056989015014139

Abstract

The title compound, K(+)·C5H11O8S(-)·H2O [systematic name: potassium (1S,2S,3S,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate monohydrate], formed by reaction of d-lyxose with potassium hydrogen sulfite in water, crystallizes as colourless square prisms. The anion has an open-chain structure in which the S atom, the C atoms of the sugar chain and the oxygen atom of the hy-droxy-methyl group form an essentially all-trans chain with the corresponding torsion angles lying between 178.61 (12) and 157.75 (10)°. A three-dimensional bonding network exists in the crystal structure involving coordination of two crystallographically independent potassium ions by O atoms (one cation being hexa- and the other octa-coordinate, with each lying on a twofold rotation axis), and extensive inter-molecular O-H⋯O hydrogen bonding.

Highlights

The title compound, K+C5H11O8SH2O [systematic name: potassium (1S,2S,3S,4R)-1,2,3,4,5-pentahydroxypentane-1-sulfonate monohydrate], formed by reaction of d-lyxose with potassium hydrogen sulfite in water, crystallizes as colourless square prisms
A three-dimensional bonding network exists in the crystal structure involving coordination of two crystallographically independent potassium ions by O atoms, and extensive intermolecular O—H O hydrogen bonding
A possible role in the stabilization of food stuffs led to early studies (Gehman & Osman, 1954) and evidence for the acyclic nature of such compounds was first provided by Ingles (1959), who reported on such adducts from d-glucose, d-galactose, d-mannose, l-arabinose and l-rhamnose

Summary

Chemical context

The bisulfite anion HSO3 exists in a complex, pH-dependent equilibrium with sulfurous acid. These sulfur compounds are widely used in the preservation of foodstuffs because of their anti-oxidant and antimicrobial properties. Dissolution of sodium or potassium metabisulfite (Na2S2O5 or K2S2O5, respectively) in water affords a mixture of such compounds, along with sulfur dioxide, and they are widely used (e.g. as food additive E223) for their anti-oxidant, bactericidal and preservative properties. A possible role in the stabilization of food stuffs led to early studies (Gehman & Osman, 1954) and evidence for the acyclic nature of such compounds was first provided by Ingles (1959), who reported on such adducts from d-glucose, d-galactose, d-mannose, l-arabinose and l-rhamnose. Conclusive proof of the acyclic nature of these bisulfite adducts was first given through the X-ray studies of Cole et al (2001) who reported the crystal structures of d-glucose- and d-mannose-derived potassium sulfonates.

Structural commentary

Spectroscopic findings

Supramolecular features