Structure of 2,2-bis(methylthio)-1,1-ethylenedicarbonitrile

Hummel, H.-U.; Procher, H.

doi:10.1107/s0108270186091321

Cited by 3 publications

(4 citation statements)

References 2 publications

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“…Figure 2), which are deviating from standard bond lengths. These bond lengths variations were also found in 5 [11a] and 7 [11b] . It is probable, that these units are resonance‐stabilized (cf.…”

Section: Figurementioning

confidence: 57%

Influence of Regioisomerism in 9‐Anthracenyl‐Substituted Dithiodicyanoethene Derivatives on Photoinduced Electron Transfer Controlled By Intramolecular Charge Transfer

et al. 2021

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In this paper, we report on the fluorescence behaviour of three regioisomers which consist of two 9‐anthracenyl fluorophores and of differently substituted dithiodicyanoethene moieties. These isomeric fluorescent probes show different quantum yields (ϕf). In these probes, an oxidative photoinduced electron transfer (PET) from the excited 9‐anthracenyl fluorophore to the dithiodicyanoethene unit quenches the fluorescence. This quenching process is accelerated by an intramolecular charge transfer (ICT) of the push‐pull π‐electron system of the dithiodicyanoethene group. The acceleration of the PET depends on the strength of the ICT unit. The higher the dipole moment of the ICT unit, the stronger the observed fluorescence quenching. To the best of our knowledge, this is the first report of a regioisomeric influence on an oxidative PET by an ICT.

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Section: Figurementioning

confidence: 57%

Influence of Regioisomerism in 9‐Anthracenyl‐Substituted Dithiodicyanoethene Derivatives on Photoinduced Electron Transfer Controlled By Intramolecular Charge Transfer

et al. 2021

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“…The crystal structures agreed well with those reported previously. [27,38,39] The structure of the centrosymmetric 5-nitrouracil polymorph (Pbca) is reported for the first time and deposited in the Cambridge Crystallographic Database.…”

Section: Methodsmentioning

confidence: 99%

“…An earlier structural report on this molecule suggested steric interaction to be responsible for the discrepancy. [27] However, 3,3-bis(methylthio)-2-nitro-2-propene-1-nitrile does not show significant differences in the bond lengths and angles between the syn-and the anti-configurations of the methylthio groups. [28] Figure 6 shows the contour maps of the negative Laplacian of the total density in the plane defined by the N1-N2-C3 atoms.…”

Section: 1-ethylenedicarbonitrilesmentioning

confidence: 96%

An Experimental Charge Density Study of the Effect of the Noncentric Crystal Field on the Molecular Properties of Organic NLO Materials

2000

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“…1, confirms the formation of the Z isomer. remaining compounds, 2,2-bis(methylthio)-l, 1-ethylenedicarbonitrile (Hummel & Procher, 1986), 1,1-bis-(methylthio)-2-p-bromobenzoyl-2-cyanoethylene (Abrahamsson, Rehnberg, Liljefors & Sandstrtim, 1974) and 3-[bis(methylthio)methylene]pentane-2,4-dione (Jarvis & Taylor, 1979), have C--S bond lengths in the range 1.716-1.819 A; a similar range is observed in the title compound but the S(1)--C(3) distance of 1.837 (3),4, is slightly longer than expected and may be due to a steric effect. The C(3)---C(4) bond of 1.354 (4),4, corresponds well to a C~C double bond.…”

mentioning

confidence: 99%