- Reaction of N-chloro-1,4-benzoquinone imines with thiols
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N-Chloro-1,4-benzoquinone imines reacted with arenethiols to give different products, depending on the conditions and initial quinone imine structure. N-(Arylsulfanyl)-1,4-benzoquinone imines were obtained as a result of nucleophilic substitution of the chlorine atom, and 1,4-benzoquinone imines containing an aryl-sulfanyl substituent in the quinoid ring were formed according to the radical mechanism. The reactions of N-chloro-1,4-benzoquinone imines with heterocyclic thiols afforded only the corresponding chlorine substitution products.
- Konovalova,Avdeenko,Santalova,Lysenko,Burmistrov
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p. 1287 - 1296
(2016/10/26)
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- Z, E-Isomerization mechanism for N-arylthio-1,4-benzoquinonimines: DNMR and DFT investigations
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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
- Pirozhenko,Rozhenko,Avdeenko,Konovalova,Santalova
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p. 811 - 817
(2008/12/23)
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