5147-73-9Relevant academic research and scientific papers
Comparison of preparation methods of N-arylsulfinyl-1,4-benzoquinone monoimines
Avdeenko,Konovalova,Santalova
, p. 231 - 236 (2008/12/20)
Advantages and shortcomings were discussed of three procedures for preparation N-arylsulfinyl-1,4-benzoquinone imines: the reaction of arenesulfenyl chlorides with 1,4-benzoquinone oximes, the oxidation of N-arylthio-1,4-benzoquinone imines, and the reaction of arylsulfinyl chlorides with p-aminophenols followed by oxidation. A series of new N-arylsulfinyl-1,4- benzoquinone imines was obtained.
Z, E-Isomerization mechanism for N-arylthio-1,4-benzoquinonimines: DNMR and DFT investigations
Pirozhenko,Rozhenko,Avdeenko,Konovalova,Santalova
, p. 811 - 817 (2008/12/23)
Z, E-Isomerization has been investigated for the series of the N-arylthio-1,4-benzoquinonimines using a line shape analysis in the 1H NMR spectra. Thermodynamic parameters and substituent effects have been analyzed for the isomerization process. It has been shown based on the DFT (B3LYP) calculations that the dynamic transformation for N-arylthio-1,4- benzoquinonimines should be considered as a combination of the two different processes, a rotation about the N-S bond and an inversion at nitrogen via the transition state with the linear C = N-S moiety. The free energies of activation for the isomerization (ΔG298 K) measured experimentally depend on the substitution in the quinonimine moiety and phenyl ring and can be referred either to the inversion of the nitrogen atom or to the hindered rotation about the N-S bond. Copyright
Reactions of arylsulfinyl chlorides and N-(arylsulfonyl)arylsulfinimidoyl chlorides with p-aminophenols
Avdeenko,Konovalova,Santalova
, p. 1471 - 1474 (2008/09/16)
In reactions of arylsulfinyl chlorides and N-(arylsulfonyl) arylsulfinimidoyl chlorides with p-aminophenols formed N-arylthio-1,4- benzoquinone imines, evidently through a stage of N-arylsulfinyl-4-aminophenols and N-(N-arylsulfonyl)arylsulfinylimidoyl-4-aminophenols that under the reaction conditions eliminate respectively H2O and ArSO2NH 2.
Synthesis and 13C NMR spectra of N-substituted para-quinone imines: II. N-arylthio- and N-arylsulfonyl-l,4-benzoquinone imines with enhanced electron-withdrawing character of the quinoid ring
Pirozhenko,Avdeenko,Yusina,Konovalova
, p. 1142 - 1148 (2007/10/03)
Introduction of chlorine substituents into quinone imine fragment results in virtually the same variations in the chemical shifts of the quinoid ring carbons both in N-arylthio and N-arylsulfonyl-1,4-benzoquinone imines as compared to the unsubstituted analogs. In both classes of chloro-substituted compounds the effect of substituents in the benzene ring on the character and the range of chemical shifts variations for the carbon signals from the quinoid ring also turned out to be identical. Any differences observed may be due to the change in the geometry of the molecules, in particular, to the increase in the bond angle C=N-S.
