Structural studies of polychlorinated hydrocarbons. III. The <i>cis</i> and <i>trans</i> isomers of tetrachlorostilbene

Norrestam, R.; Hovmöller, Sven; Palm, T.-B.; Göthe, Rolf; Wachtmeister, Carl Axel

doi:10.1107/s0567740877003690

Cited by 6 publications

(4 citation statements)

References 4 publications

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“…There are no significant differences between corresponding bond distances in compounds 1 and 2 and they compare well with those reported for E-and Z-dichlorostilbene (13). In both structures, the ethene fragment suffers from considerable strain in the bond angles, which deviate significantly from 120".…”

Section: Resultssupporting

confidence: 70%

“…1" and 82.2" for the Z and E forms, respectively) show that the phenyl groups have quite similar and roughly normal orientations with respect to the ethene plane. This conformation differs significantly from those observed for the Z and E isomers of tetrachlorostilbene (1,2-dichloro-1,2-bis(4-ch1orophenyl)ethylene) (13,14), characterized by torsion angles of about 54 and 75", respectively. It appears that the larger dihedral angles between the phenyl rings and the ethene plane in these compounds can be attributed mainly to the repulsive interaction between the Cl(1) and Cl(2) atoms (Table 4).…”

Section: Resultsmentioning

confidence: 48%

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Crystal and molecular structure of Z- and E-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene. An X-ray and NMR study

Antolini¹,

Folli²,

Iarossi³

et al. 1995

Can. J. Chem.

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Abstract:The crystal structures of the title compounds were determined by single crystal X-ray diffraction techniques. The molecule of the Z isomer, which crystallizes in the monoclinic space group C21c with Z = 4 in a cell of dimensions a = 14.891 (2), b = 10.780(2), c = 8.769(1) A, P = 97.47(2)", V = 1395.7(7) A3, has crystallographic twofold symmetry. The E form crystallizes in the orthorhombic space group Pbca with a = 11.730(1), b = 6.932(1), c = 16.841(1)A, V = 1369.4(2) A3, and Z = 4. Its molecules have crystallographically dictated symmetry. In both isomers the phenyl rings are roughly perpendicular to the average ethylene plane. The atoms characterizing this plane show significant deviations from planarity in the Z isomer. Marked bondangle distortions at the ethene carbons of both structures are observed. The 'H and I3c NMR spectra of the compounds were measured and, particularly in the case of the 'H chemical shifts, fall into two quite separate spectral regions. At low temperature, two conformational isomers, those with different relative orientation of the C-C1 bonds of the phenyl rings, are observed in the spectrum of each compound.Key words: chlorostilbenes, overcrowded molecules, X-ray structure, conformations, NMR spectroscopy. Ses molCcules existent dans une symttrie dictte par sa cristallographie. Dans les deux isomkres, les noyaux phtnyles sont approximativement perpendiculaires au plan moyen de 1'Cthyltne. Dans I'isomere Z, les atomes caractensant ce plan prtsentent des deviations significatives par rapport h la plankite. Dans les deux structures, on a observe des distorsions marqutes dans les angles de liaison des carbones de 1'Cthkne. On a dktermin6 les spectres RMN du 'H et du l3c et les deplacements chimiques, particulikrement du 'H, sont divists en deux rtgions spectrales bien distinctes. A basse temperature, dans chacun des composts, on a observt deux isomkres conformationnels qui different par l'orientation relative des liaisons C-C1 par rapport aux noyaux phtnyles.

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 48%

Crystal and molecular structure of Z- and E-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene. An X-ray and NMR study

Antolini¹,

Folli²,

Iarossi³

et al. 1995

Can. J. Chem.

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“…Hence, although the trans isomer of 5 is the favored synthetic product, the cis isomer is the predominant biosynthetic metabolite. a,a',4,4'-Tetrachlorostilbene is alleged to be a DDT degradation product, and the crystal structures for both cis and trans isomers have been reported (Norrestam et al, 1977;De Kok and Romers, 1978).…”

Section: Resultsmentioning

confidence: 99%

Metabolism of 4-chlorobenzotrichloride in rats

Quistad¹,

Mulholland²,

Skiles³

et al. 1985

J. Agric. Food Chem.

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“…278 K). Crystal structures are known for cis-1,2-dichlorostilbene (Hey et al, 1984) and the chloro-substituted stilbene cis-bis(4chlorophenyl)-1,2-dichloroethene (Norrestam et al, 1977).…”

mentioning

confidence: 99%

cis-1,2-Dibromo-1,2-diphenylethene–diphenylethyne (2/1)

Barnes

Chudek

2002

Acta Cryst E

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The molecular components, 2C14H10Br2·C14H10, are arranged in separate stacks in this ordered structure. There is no evidence of π–π intermolecular interaction. Diphenylethyne lies on a crystallographic inversion centre. The structure can be represented as centrosymmetric trimolecular units, held together by a C—H⋯ring interaction between a stilbene and each of the phenyl groups of the diphenylethyne (H⋯Cgring 2.66 Å; Cgring indicates a ring centroid).

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Structural studies of polychlorinated hydrocarbons. III. The cis and trans isomers of tetrachlorostilbene

Cited by 6 publications

References 4 publications

Crystal and molecular structure of Z- and E-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene. An X-ray and NMR study

Crystal and molecular structure of Z- and E-1,2-dichloro-1,2-bis(2-chlorophenyl)ethylene. An X-ray and NMR study

Metabolism of 4-chlorobenzotrichloride in rats

cis-1,2-Dibromo-1,2-diphenylethene–diphenylethyne (2/1)

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