120697-23-6Relevant academic research and scientific papers
Thermal Equilibration of Z- and E-Isomers of 5-Arylmetylenehydantoins. Evidence for Non-bonded Aromatic ?...Methyl Attractions
Tan, Sau-Fun,Ang, Kok-Peng,How, Gee-Fung
, p. 2045 - 2050 (2007/10/02)
Standard free energy differences between the Z- and E-isomers of 14 5-arylmethylenehydantoins have been estimated by thermal equilibration in dimethyl sulphoxide.The Z-configuration is more stable for the N-substituted compounds while the E-configuration is preferred for those N-1 methyl derivatives with only para-substituents in the aryl group.The ΔG0 values vary with the nature of the para substituents.For those N-1 methyl derivatives with two ortho-substituents in the aryl group, the configurational preference is dependent on the electronic effects of these aryl subtituents, suggesting the presence of non-bonded aromatic ?...Me interactions.The factors influencing the relative stabilities of Z- and E-isomers are discussed.
