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- W2096512902 abstract "The kinetics of the nitrosation reaction of several substituted sulfonamides and of the denitrosation of the resulting products have been studied. The denitrosation rate is first-order with respect to both the nitroso compound and acid concentration and no effect of added nucleophiles was observed. The denitrosation reaction is general-acid catalysed, with a Brønsted parameter, αd, of 0.7, which is independent of the substituents on the aromatic ring. Kinetic solvent isotope effects range from kdH3O+/kdD3O+ = 1.20 ± 0.05 to 2.04 ± 0.06 for denitrosation by L3O+ and from kdAH/kdAD = 1.5 ± 0.2 to 2.3 ± 0.3 for denitrosation by dichloroacetic acid, which suggest that a rate-determining proton transfer is involved in this reaction. For nitrosation reaction, the absence of catalysis by nucleophilic anions, the observed general-base catalysis (βNO = 0.3) and the substituent effects suggest a concerted nitrosation–denitrosation process. The Leffler parameters obtained for N· · ·H bond formation (αnuc = 0.7) as well as for N· · ·NO bond breaking (αlg = 0.17) are in favour of an imbalance in the transition state (αimbalance = 0.53) with the development of a positive charge on the nitrogen adjacent to the nitroso group." @default.
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- W2096512902 date "1998-01-01" @default.
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- W2096512902 title "Nitrosation and denitrosation of substituted N-methylbenzenesulfonamides. Evidence of an imbalanced concerted mechanism" @default.
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- W2096512902 doi "https://doi.org/10.1039/a801275j" @default.
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