A gas electron diffraction study of the molecular structure of trans-stilbene

Trætteberg, M.; Frantsen, E.B.; Mijlhoff, F.C.; Hoekstra, A.

doi:10.1016/0022-2860(75)80066-4

Cited by 166 publications

(93 citation statements)

References 16 publications

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“…In the trans isomer, the CI(¢t)-..C(1) and Cl(a)...C(l') intramolecular distances are 2.86 and 2.88, while Cl(a)... C(6) and Cl(tt)... C(2') are 3.41 and 3.39 ,~ respectively. The stilbene conformations obtained agree to some extent with those recently found in gas electron diffraction studies of cis and trans-stilbene (Traetteberg, Frantsen, Mijlhoff & Hoekstra, 1975;. However, their torsional angles describing the orientations of the phenyl groups are considerably smaller (43 and 32 ° respectively) than those found in the present study (54 and 75 o respectively).…”

Section: Introductionsupporting

confidence: 88%

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

Norrestam¹,

Hovmöller²,

Palm³

et al. 1977

Acta Crystallogr Sect B

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The c/s and trans isomers of 1,2-bis(4-chlorophenyl)-1,2-dichloroethylene, C14HsC14, are monoclinic, space group P21/c. The 107 parameters describing the trans isomer [a = 6.002 (5), b = 14.500 (12), c = 7.630 (5) A,/~ = 94.55 (2) °, Z = 2, Dx = 1. 596 g cm-31 were refined versus the 854 most significant single-crystal Xray reflexions to an R of 0.043. The 195 parameters of the cis isomer [a = 8.062 (8), b = 28.560 (12), c = 6.118 (6) A,/3 = 97.60 (2) °, Z = 4, Dx = 1.513 g cm-31 were refined versus the 1017 most significant reflexions to an R of 0.048. The molecules of both isomers were found to be nonplanar. The C-C=C bond angles at the ethylene bridge were significantly greater than 120 (125) for the cis isomer and less than 120 ° ( 118 o) for the trans isomer.

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Section: Introductionsupporting

confidence: 88%

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

Norrestam¹,

Hovmöller²,

Palm³

et al. 1977

Acta Crystallogr Sect B

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“…This value is slightly longer than the 14/14 CASSCF result, and it is also longer than the experimentally accepted value, which is between 1.33 and 1.35 Å. [30][31][32] The latter value is most likely correct, because this bond should be longer than in ethylene, due to conjugation with the phenyl rings. It appears that CASSCF with all π-orbitals active gives accurate geometries.…”

Section: Geometries and Relative Energiesmentioning

confidence: 81%

Theoretical Study of the Lowest¹B_UStates oftrans-Stilbene

et al. 2002

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The results of a theoretical study of the ground state, 1 1 A g , and of the lowest 1 B u states of trans-stilbene are presented. The vertical and adiabatic excitation energies of the lowest 1 B u states have been computed using multiconfigurational SCF theory, followed by second-order perturbation theory. It is shown that the two lowest excited states are separated by a small energy gap in the Franck-Condon region. They are the 1 1 B u , characterized by the HOMOfLUMO single excitation substantially localized on the ethylenic moiety, and the 2 1 B u , formed by a combination of one electron excitations localized mainly on the benzene rings. The most intense transition is found to be the lowest in energy when the interaction between different states is included at the level of second-order perturbation theory. The vibronic structure of emission and absorption spectra of the two lowest 1 B u states have been determined within the Franck-Condon approximation. The spectrum calculated for the 1 1 B u state agrees with the experimental spectrum, while the low intensity band computed for the 2 1 B u state has no experimental counterpart. It is concluded that this band is buried in the strong 1 1 B u absorption and therefore not observed.

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“…I While the molecular structure of trans-stilbene appears to be I approximately planar in the solid state (40), its gas phase I structure is found to be nonplanar (41). However, the potential ( curve for energy vs. the dihedral angle is very shallow and the 1 calculated energy barrier corresponding to the C, conformation I is only about 0.5 kcal mol-' (17).…”

Section: Discussionmentioning

confidence: 99%

Charge distributions and chemical effects. XL. Chemical bonds in benzenoid hydrocarbons

Fliszár¹,

Cardinal²,

Baykara³

1986

Can. J. Chem.

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Benzenoid hydrocarbons were examined using a bond energy scheme featuring the role of atomic charges. The latter were conveniently deduced from appropriate correlations between theoretical results and 13C nuclear magnetic resonance shifts. Atomization energies calculated in this manner agree with their experimental counterparts to within 0.36 kcal mol-1 (average deviation). It appears that benzenoid hydrocarbons can be efficiently described in terms of local charge density properties. In the absence of any distinctive specific feature characterizing benzenoids, this particular description of chemical bonds ultimately results in a unifying genealogy smoothly relating to one another the various possible types of CC and CH bonds which are formed by sp2 and sp3 carbons.

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A gas electron diffraction study of the molecular structure of trans-stilbene

Cited by 166 publications

References 16 publications

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

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

Theoretical Study of the Lowest¹B_UStates oftrans-Stilbene

Charge distributions and chemical effects. XL. Chemical bonds in benzenoid hydrocarbons

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A gas electron diffraction study of the molecular structure of trans-stilbene

Cited by 166 publications

References 16 publications

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

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

Theoretical Study of the Lowest1BUStates oftrans-Stilbene

Charge distributions and chemical effects. XL. Chemical bonds in benzenoid hydrocarbons

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Theoretical Study of the Lowest¹B_UStates oftrans-Stilbene