61866-00-0Relevant academic research and scientific papers
Structure-Stability Relationships in Vinyl Sulfides. III. Stabilization Caused by Different Alkylthio and Phenylthio Groups Attached to an Olefinic Double Bond
Kimmelma, Reijo
, p. 550 - 555 (2007/10/02)
The stabilization energies of different alkylthio and phenylthio groups attached to an olefinic double bond have been evaluated with respect to the energy differences of the isomerization reactions of some unsaturated sulfides, in which the double bond migrates from the β,γ- to the α,β-position.According to these results the stabilization energies (in kJ mol-1) are: MeS 15.6, EtS 14.8, i-PrS 15.7, t-BuS 17.5 and PhS 14.4
Structure-Stability Relationships in Vinyl Sulfides. I. On the Stable Conformations of Vinyl Sulfides
Virtanen, Reijo
, p. 313 - 327 (2007/10/02)
A thermodynamic and 13C NMR spectroscopic study of the structures of the less stable rotamers of alkyl vinyl sulfides have been performed.It has been shown that the less stable rotamer of methyl vinyl sulfide has the planar s-trans configuration and the proportion of this is about 20percent.The energy difference between the planar s-cis and s-trans is about 3.5 kJ mol-1.Ethyl vinyl sulfide is almost an equimolar mixture of the planar s-cis and s-trans conformations.The 13C NMR data showed that the p-? cojugation in the compounds that could not adopt any of the planar arrangements was decreased.In alkyl 1-propenyl sulfides, the stabilizing interaction between the methyl group and the S atom cis to each other was ca.1.8 kJ mol-1.The most probable choice for the most stable conformation of di-1-propenyl sulfides is the planar (or nearly planar) s-trans,s-trans one.
