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• W2020172598 abstract "A two-step mechanism of the reaction of CH3CoIIIPc (Pc = dianion of phthalocyanine) with thiophenoxides in DMA has been confirmed, and the visible spectrum of the inactive transient, CH3CoIIIPc(SAr)-, has been determined. Rapid rates for ligation of CH3CoIIIPc, yielding CH3CoIIIPc(S−C6H4−X)-, are virtually independent of X; this step proceeds probably by an Id mechanism. Kinetic data for the follow-up methyl-transfer step yield second-order rate constants and stability constants for CH3CoIIIPc(S−C6H4−X)- consistent with those estimated from concentration dependence of the amplitude of the ligand-exchange step. Cyclic voltammetry provides first reduction potential for CH3CoIIIPc(DMA) of −1.42 V vs Fc+/Fc, which makes an OSET mechanism unlikely. Homolytic decay of CH3CoIIIPc(SAr)- has also been ruled out. All of the kinetic data, including Hammett's ρ = −2.3 ± 0.1, N-donor inhibition, and alkyl group effect, Me > Et, indicate that the reaction is a normal SN2 methyl transfer, only very fast. Methyl transfer to aliphatic thiolates is also rapid and follows the same SN2 mechanism. Exceptional methyl-transfer reactivity of the phthalocyanine model sharply contrasting with the inertness of methylcobaloxime is explained." @default.
• W2020172598 created "2016-06-24" @default.
• W2020172598 creator A5030168089 @default.
• W2020172598 date "2005-06-25" @default.
• W2020172598 modified "2023-09-24" @default.
• W2020172598 title "Methyl Transfer from CH₃Co^IIIPc to Thiophenoxides Revisited: Remote Substituent Effect on the Rates" @default.
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• W2020172598 doi "https://doi.org/10.1021/ic0503378" @default.
• W2020172598 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16022546" @default.
• W2020172598 hasPublicationYear "2005" @default.
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