Absolute sense of twist of the benzil molecule in its enantiomorphous crystals and inclusion complexes with optically active hosts

Połoński, Tadeusz; Szyrszyng, Monika; Gdaniec, Мaria; Nowak, E.; Herman, Aleksander

doi:10.1016/s0957-4166(01)00127-6

Cited by 22 publications

(18 citation statements)

References 29 publications

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“…Dehydrocholic acid (Vi) is known to be an effective host for the enantioresolution of sulfoxides and cyclic amides [118][119][120][121]. It is noteworthy that Ia includes chiral conformers of achiral compounds [122][123][124].…”

Section: Chirality Recognition Based On Supramolecular Chiralitymentioning

confidence: 99%

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

2007

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Abstract:Steroidal bile acids and their derivatives exhibit characteristic inclusion behaviors in the crystalline state. Their crystals present varied assemblies due to asymmetric molecular structures, which relate to supramolecular properties through cooperative weak interactions. An overview indicates that the steroidal assemblies lie in an intermediate position among various molecules and have hierarchical structures such as primary, secondary, tertiary, and host-guest assemblies like proteins. Such an interpretation brought about the idea that the assemblies with dimensionality present supramolecular chirality such as three-axial, tilt, helical, bundle, and complementary chirality. This concept of the supramolecular chirality enables us to understand formation of chiral crystals starting from the molecular chirality of the steroidal molecules.

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Section: Chirality Recognition Based On Supramolecular Chiralitymentioning

confidence: 99%

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

2007

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“…This occurs when the molecules, although achiral, are fixed in a chiral conformation or arranged in a chiral manner in a crystal lattice. Gdaniec and Polonski reported this observation for the inclusion compounds of cholic 1 and deoxycholic acid 3 with various aromatic ketones 68,69 and diketones, 70 …”

Section: Achiral Organic Guestsmentioning

confidence: 70%

Bile acids in asymmetric synthesis and chiral discrimination

2009

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“…The obtained optical-rotatory dispersion formula is used to create the circular-dichroism formula based on the connection of the opticalrotatory dispersion and circular dichroism by the Kramers-Kronig transforms (2), (3). This theoretical circular-dichroism curve is compared with the available experimental data [9,12].…”

Section: Figurementioning

confidence: 99%

“…Recently the solid-state circular-dichroism spectra were measured for the crystal of benzil [12]. The circular-dichroism spectra were obtained with freshly prepared KBr disks and recorded with a Jasco-715 dichrograph.…”

Section: Interpretation Of the Latest Measurement Of Circular-dichroimentioning

confidence: 99%

“…This measurement is consistent with those of Perekalina et al [9] with the advantage that Moxon, Renshaw, and Tebbutt's results were obtained simultaneously for the circular dichroism and optical-rotatory dispersion in one experiment. The last experimental study of the benzil-crystal optical activity was made by Polonski et al [12]. They compared the circular dichroism spectra of the benzil crystalline inclusion complexes with cholic and deoxycholic acids.…”

Section: Introductionmentioning

confidence: 99%

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Theory, Measurement, and Origin of Optical Activity in Benzil Crystal

Řı́ha

Vyšín

Lapšanská

2005

Molecular Crystals and Liquid Crystals

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The three coupled oscillator model and its application to the explanation of opticalrotatory dispersion and circular dichroism of benzil crystal is discussed. The previously measured experimental data are approximated by the theoretical set of formulas provided by this model. The twelve-term formula, which was computed using our computer program, is derived from the interpretation of the opticalrotatory dispersion of benzil. Similarly, the circular-dichroism data are analyzed. Both the previously published experimental data and the latest measurements are used for this reason. The obtained results are compared and discussed with respect to the origin of the optical activity occurring in benzil crystal.

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Absolute sense of twist of the benzil molecule in its enantiomorphous crystals and inclusion complexes with optically active hosts

Cited by 22 publications

References 29 publications

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

Bile acids in asymmetric synthesis and chiral discrimination

Theory, Measurement, and Origin of Optical Activity in Benzil Crystal

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