Structure of bis(μ-pyridine-2-thione-μ-S)-bis[iodo(pyridine-2-thione-S)copper(I)]

Mentzafos, D.; Terzis, A.; Karagiannidis, P.; Aslanidis, P.

doi:10.1107/s0108270188010546

Cited by 21 publications

(14 citation statements)

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“…We have found that χ 1 and χ 2 have a weak dependence on the side chain conformation. Our results are in good agreement with X-ray data for cercosporin [26,28], whereas for phleichrome no structural data are available. However, the prediction that χ 1 ~ χ 2 ~ 30° appears reasonable for 2 , considering that the narrower χ 1 angle in cercosporin is a consequence of the constraints imposed by the bridge in the “6,7-bay region”.…”

Section: Resultssupporting

confidence: 88%

“…Our calculations confirm that the “propeller” form, found in X-ray structures of 1 [26,28], is significantly more stable than the other, called “double butterfly” by Falk and co-workers [37]. The two geometries, as obtained for the g + g + conformer of 1, are shown in Fig.…”

Section: Resultssupporting

confidence: 84%

“…To limit the computational cost, we only considered the ( p , p ) states. This is the state found in one of the available X-ray structures of cercosporin [26], whereas the other structure has the methoxy groups in the ( m , p ) state [28]. …”

Section: Resultsmentioning

confidence: 99%

“…Of the two X-ray structures of cercosporin reported in the literature, one has the side chains in the g + g + [28] and the other in the g − g − conformation [26]. These do not appear to be compatible with the strong preference for the trans state predicted by B3LYP calculations, but the conformational preferences in crystals might be biased by the environment.…”

Section: Resultsmentioning

confidence: 99%

“…Cercosporin and phleichrome are characterized by a special coupling between conformation and configuration: The conformational preferences of the side chains in the “1–12 bay region” are critical for the generation of the helical structure. X-ray crystallography established the R , R configuration at C14 and C17 of cercosporin ( 1 ) and the sign of the axial chirality as M [26,28]. Phleichrome ( 2 ) features opposite chirality, having P axial chirality and S , S configuration at C14 and C17 [27].…”

Section: Introductionmentioning

confidence: 99%

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The interplay of configuration and conformation in helical perylenequinones: Insights from chirality induction in liquid crystals and calculations

Frezza¹,

Pieraccini²,

Mazzini³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe chirality transfer in liquid crystals induced by two helical perylenequinones (namely, the natural compounds cercosporin and phleichrome) was investigated by integrating measurements of helical twisting power with a conformational analysis by DFT calculations and with the prediction of their twisting ability by the surface-chirality method. The two quasi-enantiomeric derivatives induce oppositely handed cholesteric phases when introduced as dopants in nematic solvents. We evaluated the role of the different conformations of the chiral hydroxyalkyl side chains in determining the helical twisting power: They were found to affect the strength of the chirality transfer, although the handedness of the induced cholesteric phase is essentially determined by the axial chirality (helicity) of the core of the perylenequinones.

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Section: Resultssupporting

confidence: 88%