Solid-state resolution of binaphthyl: crystal and molecular structures of the chiral (A)1 form and racemic (B)1 form and the study of the rearrangement of single crystals. Requirements for development of hemihedral faces for enantiomer identification

Kress, Ruth B.; Duesler, Eileen N.; Etter, Margaret C.; Paul, Iain C.; Curtin, David Y.

doi:10.1021/ja00546a012

Cited by 86 publications

(60 citation statements)

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Section: X-ray Diffraction Analysismentioning

confidence: 99%

“…Structures of pure chiral and racemic crystals 24,25 were also characterized by XRD analysis as references. The procedure for the preparation of the tetragonal-bipyramidal chiral crystal 25 was the same as in our previous report. 22 Thin plates of the racemic crystal 25 were prepared by slowly evaporating acetone from racemic 1,1V-binaphthyl acetone solution.…”

Section: X-ray Diffraction Analysismentioning

confidence: 99%

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Chiral symmetry‐breaking transition in growth front of crystal phase of 1,1′‐binaphthyl in its supercooled melt

et al. 2004

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Although the theory of spontaneous chiral symmetry-breaking in open systems was proposed some time ago, experimental realization of this phenomenon has not been achieved. In this article, we note that the crystal growth front of 1,1'-binaphthyl shows many of the characteristics of an open system in which chiral symmetry-breaking has occurred. We studied the temperature profiles of the crystallizing surface and obtained X-ray diffraction data of the crystals grown from the melt under controlled conditions. The data show that, under appropriate conditions, the observed bimodal probability distribution of enantiomeric excess (ee) with maxima approximately 60% is due exclusively to chiral crystals and not due to racemic crystals of 1,1'-binaphthyl that can also form at large supercooling. The mass independence of the ee shows that the growing front maintains a constant ee, which is a clear signature of open systems in steady state. Chirality 16:131-136, 2004.

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Section: X-ray Diffraction Analysismentioning

confidence: 99%

Section: X-ray Diffraction Analysismentioning

confidence: 99%

Chiral symmetry‐breaking transition in growth front of crystal phase of 1,1′‐binaphthyl in its supercooled melt

et al. 2004

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“…u,,, Naphthidine 1070 (6) 193 (7) 2654 (8) 250 ( 10) 3852 (8) 1496 ( 12) 3430 ( 10) 26 1 5(9) 1381 (12) 3705(9) -133 (13) 3595(12) -1340 (12) 2458(1 1) -954 (8) 1363(8) 653 (7) 1385 ( (3) 2755 (3) was encountered in locating the hydrogen atoms; the ring H atoms were placed in ideal calculated positions, and the two amino hydrogen atoms were assigned to the most chemically plausible peaks near the nitrogen atom on a difference map. Refinement of C and N parameters was then completed to final R = 0.068 and R,,.…”

Section: Methodsmentioning

confidence: 99%

“…In a continuing study of these phenomena the crystal structure of optically active naphthidine has now been investigated. Since the crystal structure of optically active 1,l '-binaphthyl was unknown, its structure has also been determined; after completion of the work two other independent studies of binaphthyl appeared (8,9), and our results are presented briefly for completeness and for comparison.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of optically active naphthidine (4,4′-diamino-1,1′-binaphthyl) and 1,1′-binaphthyl

Pauptit¹,

Trotter²

1983

Can. J. Chem.

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A, respectively, Z = 4. The structures were solved by direct methods and refined by full-matrix least-squares techniques to respective R = 0.068 and 0.030 for 548 and 562 reflexions. The dihedral angles between the planes of the naphthalene residues are 87 and l02", respectively. Bond lengths and angles are normal. RICHARD A. PAUPTIT et JAMES TROTTER. Can. J. Chem. 61, 69 (1983). Les cristaux de naphtidi!e et de binaphtyle actifs optiquement sont tetragonals, P4,2,2 (ou P4,2,2), o = 7.945(1), 7.164(2), c = 24.264(5), 27.70(1) A, respectivement, Z = 4. On a resolu les structures par les methodes directes et on les a affinees par la methode des moindres carres (matrice entikre) jusqu'i des valeurs respectives de R = 0.068 et 0.030 pour 548 et 562 reflexions. Les angles dikdres entre les plans des residus naphtalCniques sont 87 et l02", respectivement. Lcs longeurs de liaison et les angles sont normales.

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“…It has been reported that the dihedral angle between the two moieties in crystals changes from 60° to 100° in binaphthyl derivatives, which means that the dihedral angle can be substantially modified in the solid state. [38][39][40] The intermolecular interactions between the molecules in the organic nanotubes are the weak interactions of van der Waals type or the hydrogen bond. It is likely that different dihedral angles between the two naphthyl chromophores may exist at the same time in the nanotubes.…”

Section: Spectra Of the Nanotubes From Bnde With The Conformationamentioning

confidence: 99%

Organic Nanotubes Prepared from Chiral Molecules by the Template Method

Zhao

Yang

et al. 2005

Chin. J. Chem.

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Organic nanotubes from two kinds of chiral molecules, R-di-2-naphthylprolinol (DNP) with an asymmetric carbon atom and R-(＋)-1,1'-bi-2-naphthol dimethyl ether (BNDE) with the conformational asymmetry, were prepared by the immersing technique using porous alumina membranes as the template. It was found that the nanotubes from DNP with an asymmetric carbon atom presented the same chirality as the solution with slight red shift of the CD signals upon the formation of the nanotubes, while no well-defined chirality could be identified for the nanotubes from BNDE with the conformational asymmetry.

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Solid-state resolution of binaphthyl: crystal and molecular structures of the chiral (A)1 form and racemic (B)1 form and the study of the rearrangement of single crystals. Requirements for development of hemihedral faces for enantiomer identification

Cited by 86 publications

References 0 publications

Chiral symmetry‐breaking transition in growth front of crystal phase of 1,1′‐binaphthyl in its supercooled melt

Chiral symmetry‐breaking transition in growth front of crystal phase of 1,1′‐binaphthyl in its supercooled melt

Crystal structures of optically active naphthidine (4,4′-diamino-1,1′-binaphthyl) and 1,1′-binaphthyl

Organic Nanotubes Prepared from Chiral Molecules by the Template Method

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