`Jumping crystals': X-ray structures of the three crystalline phases of (±)-3,4-di-O-acetyl-1,2,5,6-tetra-O-benzyl-myo-inositol

Steiner, Th.; Hinrichs, W.; Saenger, Wolfram; Gigg, Roy

doi:10.1107/s0108768193000795

Cited by 54 publications

(50 citation statements)

References 8 publications

(10 reference statements)

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“…Both determinations showed the cyclohexane ring to exist in the chair conformation with one of the six hydroxyl groups axial and the others equatorial (la/5e). The distortion of the ring from a perfect chair was small in both cases; this was also observed in the fully protected derivatives, 1,2,3,4,5,6-C40H4406 hexa-O-acetyl myo-inositol (Abboud, Simonsen, Voll & Younathan, 1990) and (+)-3,4-di-O-acetyl-1,2,5,6-tetra-O-benzyl myo-inositol (Steiner, Hinrichs, Saenger & Gigg, 1993). Ion binding to myo-inositol by magnesium chloride (Blank, 1973) and calcium bromide (Cook & Bugg, 1973) as hydrate complexes has been shown to impose more noticeable ring distortion but still retain the expected (la/5e) conformation.…”

Section: Obnsupporting

confidence: 58%

See 1 more Smart Citation

3,4,5,6-Tetra-O-benzyl-cis-1,2-O-cyclohexylidene myo-Inositol

Spiers¹,

Schwalbe²,

Freeman³

1996

Acta Crystallogr C

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Section: Obnsupporting

confidence: 58%

“…The four O-benzyl groups each have three bonds about which rotation may occur and consequently they exhibit conformational flexibility, as shown in the crystal structure of (4-)-3,4-di-O-acetyl-1,2,5,6-tetra-O-benzyl myo-inositol (Steiner, Hinrichs, Saenger & Gigg, 1993).…”

Section: Obnmentioning

confidence: 99%

3,4,5,6-Tetra-O-benzyl-cis-1,2-O-cyclohexylidene myo-Inositol

Spiers¹,

Schwalbe²,

Freeman³

1996

Acta Crystallogr C

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“…Usually it is the other way round. [18,33,39,40] It is an example of the limitation of the close-packing principle: the more tightly packed polymorph, may have lower free energy, [33] as a balance of the repulsive H···H and the only occurring attractive CÀH···O forces. Also unusual is the behavior of form A on cooling from 110 K to 25 K. The unit cell volume increases by 5.4 (7) 3 (0.7 %).…”

mentioning

confidence: 99%

A Classical Example of a Disappearing Polymorph and the Shortest Intermolecular H⋅⋅⋅H Separation Ever Found in an Organic Crystal Structure

Bombicz¹,

Czugler²,

Tellgren³

et al. 2003

Angew Chem Int Ed

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Missing in action: Neutron and X‐ray diffraction studies at low temperatures reveal the delicate balances of attractive and repulsive intermolecular interactions in the dimorphs of 1,2,3,5‐tetra‐O‐acetyl‐β‐D‐ribofuranose (the less stable polymorph is shown, O red, H blue, C gray). Very short intermolecular H⋅⋅⋅H contacts which are only present in the less stable crystal form are responsible for the disappearance of this polymorph.

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“…We have studied the FT Raman spectra of 3,4-di-Oacetyl-1,2,5,6-tetra-O-benzyl-myo-inositol [6] (Fig. 1), which exists in three monoclinic modifications: I (at 18°C) P2 1 /c, Z=8; II (at 18°C) P2 1 /c, Z=4; III (at 80°C) P2 1 /c, Z=4.…”

Section: Resultsmentioning

confidence: 99%

Non-destructive NIR-FT-Raman analyses in practice. Part II. Analyses of 'jumping' crystals, photosensitive crystals and gems

Andreev

Schräder

Boese

et al. 2001

Fresenius' Journal of Analytical Chemistry

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Using an improved sampling arrangement we observed the FT Raman spectra of the different phases of a 'jumping crystal', an inositol derivative. The phase transition produced -as consequences of large changes of the unit cell constants -changes in frequency and intensity mainly of CH deformation vibrations. Photochemical reactions, usually produced with light quanta in the visible range, are not activated with the quanta from the Nd:YAG laser at 1064 nm. The Raman spectra of the 'dark' form of a dinitrobenzyl pyridine and afterwards the 'light' form, the product of its illumination in the visible range, were recorded. We could not observe changes of most bands, especially not of the NO 2 -vibrations; however, a new strong band appeared at 1253 cm -1 , which may be due to the expected NH-photo-isomer. Genuine gemstones and fakes can be unambiguously identified by FT Raman spectroscopy. This is especially useful for the stones whose physical properties are quite similar to those of diamonds -moissanite and zirconia. The quality of diamonds can be estimated from relative band intensities; however, this is not in complete agreement with the internationally accepted visual qualification. Synthetic diamonds produced by CVD (chemical vapor deposition) show remarkable differences from natural ones in their FT-Raman spectra.

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`Jumping crystals': X-ray structures of the three crystalline phases of (±)-3,4-di-O-acetyl-1,2,5,6-tetra-O-benzyl-myo-inositol

Cited by 54 publications

References 8 publications

3,4,5,6-Tetra-O-benzyl-cis-1,2-O-cyclohexylidene myo-Inositol

3,4,5,6-Tetra-O-benzyl-cis-1,2-O-cyclohexylidene myo-Inositol

A Classical Example of a Disappearing Polymorph and the Shortest Intermolecular H⋅⋅⋅H Separation Ever Found in an Organic Crystal Structure

Non-destructive NIR-FT-Raman analyses in practice. Part II. Analyses of 'jumping' crystals, photosensitive crystals and gems

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