Abstract
The title salt, Na+·C6H13O9S- [systematic name: sodium (1S,2S,3S,4R,5R)-1,2,3,4,5,6-hexa-hydroxy-hexane-1-sulfonate], is formed by reaction of d-mannose with sodium bis-ulfite (sodium hydrogen sulfite) in water. The anion has an open-chain structure with the S atom and the C atoms of the carbohydrate chain forming an essentially planar zigzag chain in which the absolute values of the torsion angles lie between 173.6 (2) and 179.9 (3)°. The sodium cations are penta--coordinated by O atoms, with one link to a carbohydrate O atom and four to O atoms of sulfonate residues in separate anions, thus creating a three-dimensional network. The carbohydrate anions are arranged in a head (-SO3-) to head (-SO3-) arrangement, thereby forming two parallel sheets linked through coordination to sodium ions, with each sheet containing inter-molecular hydrogen bonds between the anionic residues. Unusually, the double sheets are not connected to neighbouring sets of double sheets, either by ion coordination or inter-molecular hydrogen bonding.
Highlights
The title salt, Na+ÁC6H13O9SÀ [systematic name: sodium (1S,2S,3S,4R,5R)1,2,3,4,5,6-hexahydroxyhexane-1-sulfonate], is formed by reaction of d-mannose with sodium bisulfite in water
The carbohydrate anions are arranged in a head (–SO3À) to head (–SO3À) arrangement, thereby forming two parallel sheets linked through coordination to sodium ions, with each sheet containing intermolecular hydrogen bonds between the anionic residues
The double sheets are not connected to neighbouring sets of double sheets, either by ion coordination or intermolecular hydrogen bonding
Summary
Adducts formed by the reaction of aldehydes and bisulfite anions have long been used for aldehyde purification since they are often crystalline, whereas the parent aldehydes are often liquids with varying stabilities on storage. The bisulfite addition products of aldoses are unusual in that they are acyclic compounds despite the fact that the parent carbohydrates exist predominantly in the cyclic, hemiacetal form Such adducts were synthesised many years ago, unequivocal proof of their acyclic nature awaited X-ray structure determination, firstly on the potassium adducts of d-glucose and d-mannose (Cole et al, 2001), of d-galactose (Haines & Hughes, 2010), d-ribose (Haines & Hughes, 2014), d-lyxose (Haines & Hughes, 2015), and of the sodium adducts of d-glucose (Haines & Hughes, 2012) and d-lyxose (Haines & Hughes, 2016).
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