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- W2019925802 abstract "The kinetics of the decomposition of the model ultimate carcinogen 2-N-(pivaloyloxy)-2-amino-α-carboline (4a), and its 9-methyl analogue (4b), in 20 vol % CH3CN−H2O, μ = 0.5 (NaClO4) at 20 °C, are consistent with the uncatalyzed N−O bond heterolysis of the neutral esters. The protonated ester 4aH+ (pKa = 1.6), detected kinetically and by spectrophotometric titration, is unreactive under these conditions. Spectrophotometric titration of 4b also indicates that a protonated species, 4bH+ (pKa = 0.9), is formed under acidic conditions. Both 4a and 4b produce electrophilic intermediates, identified as the nitrenium ions 5a and 5b, that are efficiently trapped by N3-, Br-, and 2‘-deoxyguanosine, d-G, without an increase in the overall rate of decomposition of the esters. N3- and d-G trapping efficiencies, kaz+/ks+ and kd-G+/ks+, for 5a and 5b are very similar to each other and are within a factor of 4 of the trapping efficiencies with N3- and d-G previously measured for the 2-fluorenylnitrenium ion (6). The tra..." @default.
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- W2019925802 date "2000-03-24" @default.
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- W2019925802 title "Characterization of the 2-(α-Carbolinyl)nitrenium Ion and Its Conjugate Base Produced during the Decomposition of the Model Carcinogen 2-N-(Pivaloyloxy)-2-amino-α-carboline in Aqueous Solution" @default.
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- W2019925802 doi "https://doi.org/10.1021/ja993433e" @default.
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