Sodium halide complexes of ribose derivatives and their unusual crystal structures

Crystalline complexes of d-ribose, d-ribono-1,4-lactone and methyl β-d-ribopyranoside with sodium halogenides were synthesized and the crystal structures determined of two lactone complexes and a methyl β-d-ribopyranoside one with varying stoichiometries and water content. [Display omitted] ► Sodium...

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Bibliographic Details
Published in:Carbohydrate research 2011-09, Vol.346 (12), p.1610-1616
Main Authors: Czugler, Mátyás, Pintér, István
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
complexing
crystal structure
Crystallization
Crystallography, X-Ray
Glycosides - chemistry
halides
Halogens
Hydrogen Bonding
Ions
lactones
Lactones - chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
ribose
Ribose - analogs & derivatives
Ribose - chemistry
Ribose derivatives
Salts
Sodium
Sodium halide complexes
X-ray crystal structures
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Summary:Crystalline complexes of d-ribose, d-ribono-1,4-lactone and methyl β-d-ribopyranoside with sodium halogenides were synthesized and the crystal structures determined of two lactone complexes and a methyl β-d-ribopyranoside one with varying stoichiometries and water content. [Display omitted] ► Sodium halide complexes of d-ribose and some of its derivatives were prepared. ► d-ribono-1,4-lactone complex crystals show varying compositions and H2O content. ► Anhydrous methyl β-d-ribopyranoside complex has an unusual 1C4 form. ► Na+ - coordination shows flexibility. ► Such complexes can be easily prepared in solid state reactions in a ball mill Crystalline complexes of d-ribose, d-ribono-1,4-lactone and methyl β-d-ribopyranoside with sodium halides were synthesized and some of their crystal structures determined. Crystal structures of two lactone complexes and a methyl β-d-ribopyranoside reveal the mode of the salt binding and the intricate interplay of cation coordination and hydrogen bonding in these complexes. When complexed with NaBr, the ribopyranoside is in the 1C4 shape whereas ribose with no salt present has the 4C1 shape. It is also demonstrated that such complexes can be easily prepared in solid state reaction using a ball mill.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.03.014