Crystal structure of 1,3,5/2,4,6-hexahydroxycyclohexane, C6H12O6, scyllo-inositol

Zaschka, Anton; Hegetschweiler, Kaspar

doi:10.1524/ncrs.2008.0155

Cited by 1 publication

(1 citation statement)

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“…Absolute values of its hydroxyl orientation torsion angles are 12°-31°. EFURIH01 (Yeon 2001) and EFURIH03 (Zaschka and Hegetschweiler 2008) also have centers of symmetry but single molecules in their unit cells. Speaking for both symmetry-related halves of all four molecules, there were two examples of 'c' interactions, two where the hydroxyls were directed away from each other, and two where they were directed towards each other.…”

Section: Scyllo Inositolmentioning

confidence: 99%

Hydroxyl orientations in cellobiose and other polyhydroxyl compounds: modeling versus experiment

French

Csonka

2011

Cellulose

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Theoretical and experimental gas-phase studies of carbohydrates show that their hydroxyl groups are located in homodromic partial rings that resemble cooperative hydrogen bonds, albeit with long H…O distances and small O-H…O angles. On the other hand, anecdotal experience with disaccharide crystal structures suggested that these clockwise 'c' or counter-clockwise (reverse 'r') sequences are not prevalent in the crystalline state. The situation was clarified with quantum mechanics calculations in vacuum and in continuum solvation, as well as Atoms-In-Molecules analyses. From the experimental side, the Cambridge Structural Database was searched. Geometric criteria for these sequences were developed. A criterion based on 120°ranges of hydroxyl orientations accepted 4% of sequences as having 'c,c' or 'r,r' orientations instead of the 7% expected based on chance. Criteria based on an O-H…O angle [ 90°a nd a 90°lower limit of the absolute value of the H-O-C…H improper torsion accepted 7.0% of the 358 sequences as 'c,c' or 'r,r'. Highly variable orientation of the hydroxyl groups in crystals was seen to depend mostly on strong inter-residue or intermolecular hydrogen bonds. That lack of specific orientation in general for the crystal structures was supported by the solvated calculations that showed very little variation in the energy when one of the hydroxyl groups in 1,2-dihydroxycyclohexane was rotated. The vacuum calculations found the energy to vary with rotation by more than 4 kcal/mol, confirming the gas-phase experiments and calculations on more complicated molecules. Molecules examined in some detail include scyllo inositol and native and methylated cellobiose.

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Section: Scyllo Inositolmentioning

confidence: 99%