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- W4250778889 abstract "The gas-phase oxidations of aniline, N-methylaniline, and N,N-dimethylaniline by FeO+ cation are examined by using mass spectrometric techniques. Although bare FeO+ is capable of hydroxylating aromatic CH bonds, the fate of the oxidation of arylamines is determined by docking of the FeO+ unit at nitrogen. The major reactions of the metastable aniline/FeO+ complex are losses of molecular hydrogen, ammonia, and water, all involving at least one N-H proton. N-alkylation results in a complete shift of the course of the reaction. The unimolecular processes observed can be regarded as initial steps of an oxidative dealkylation of the amines mediated by FeO+. More detailed mechanistic insight is obtained by examining the CH(D) bond activation of N-methyl-N-([D3]-methyl)aniline by bare and ligated FeO+ species. The gas-phase reactions of FeO+ with methylanilines show some similarities to the enzymatic dealkylation of amines by cytochrome P-450. The kinetic isotope effects observed experimentally suggest an electron transfer mechanism for the gas-phase reaction.Key words: mass spectrometry, gas-phase chemistry, iron, dealkylation, N,N-dimethylaniline." @default.
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- W4250778889 date "1999-01-01" @default.
- W4250778889 modified "2023-09-27" @default.
- W4250778889 title "Oxidative dealkylation of aromatic amines by bare FeO<sup>+</sup> in the gas phase" @default.
- W4250778889 doi "https://doi.org/10.1139/cjc-77-5-6-774" @default.
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