Abstract
The title compound, K(+)·C5H11O8S(-) [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-penta-hydroxy-pentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates. The anion has an open-chain structure in which the S atom and the C atoms of the sugar chain, excepting that of the hy-droxy-methyl group, form an essentially all-trans chain; the C atom of the hy-droxy-methyl group lies in a gauche relationship with the three contiguous C atoms. Through complex cation coordination (through seven oxygen atoms of six different anions) and inter-molecular O-H⋯O hydrogen bonding, a three-dimensional bonding network exists in the crystal structure.
Highlights
The title compound, K+C5H11O8S [systematic name: potassium (1R,2R,3R,4R)-1,2,3,4,5-pentahydroxypentane-1-sulfonate], formed by reaction of d-ribose with potassium hydrogen sulfite in water, crystallizes as colourless plates
Atoms of the sugar chain, excepting that of the hydroxymethyl group, form an essentially all-trans chain; the C atom of the hydroxymethyl group lies in a gauche relationship with the three contiguous C atoms
1954) and evidence for their acyclic nature was first provided by Ingles (1959), who prepared such adducts from dglucose, d-galactose, d-mannose, l-arabinose and l-rhamnose
Summary
Addition compounds formed between carbonyl compounds and the bisulfite anion have found use in purification of liquid aldehydes when, as is often the case, the adduct is crystalline, in facilitating cyanohydrin formation, and in conferring required water solubility to certain hydrophobic compounds (Clayden et al, 2012). Less well known is the fact that aldoses, despite existing preferentially in the hemiacetal form, can react with the bisulfite anion to give open-chain adducts which, as chiral hydroxysulfonic acids, have potentially useful but largely unexplored applications in synthesis. The knowledge of such compounds was initially centred on the their possible role in the stabilization of food stuffs The crystal structure of the potassium bisulfite adduct of dehydro-l-ascorbic acid, first prepared by Ingles (1959), has been reported We report here the preparation in crystalline form of the hitherto unknown potassium bisulfite adduct from d-ribose, (1), and its solidstate structure
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