期刊
SCIENTIFIC REPORTS
卷 11, 期 1, 页码 -出版社
NATURE PORTFOLIO
DOI: 10.1038/s41598-021-82190-8
关键词
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资金
- National Key Research and Development Program of China [2016YFF0200503]
- National Natural Science Foundation of China [21927810]
This study reports the gas-phase amination reaction of aromatic hydrocarbons under corona discharge conditions with N-2 gas as the nitrogen source. Unusual product ions were observed and identified through high resolution MS and tandem mass spectrometric analysis. The findings provide insights into a potential mechanism for synthesizing anilines in a novel and environmentally friendly manner.
This paper reports on the gas-phase amination reaction of aromatic hydrocarbons occurring under corona discharge conditions with N-2 gas as the nitrogen source. The corona discharge device within an atmospheric pressure chemical ionization source was employed to achieve the plasma-assisted N-2 fixation, and the coupled ion trap mass spectrometer (IT-MS) was used to detect positively charged product ions. In the model case, under APCI conditions, unusual product ions, [M+16](+) and [M+14](+), were observed. Based on the high resolution MS data and tandem mass spectrometric information, [M+16](+) was confirmed to be protonated p-toluidine and [M+14](+) was confirmed to be p-methylphenylnitrenium ion. According to the experimental results of the isotopic labelling and substituent effect, one feasible mechanism is proposed as follows. Firstly, N-2 is activated by plasma caused via the corona discharge and then electrophilically attacks toluene, yielding the key intermediate, p-methylphenylnitrenium; secondly, the intermediate undergoes double-hydrogen transfer reaction to give rise to the final product ion, protonated p-toluidine. This study may provide a novel idea to explore new and green method for the synthesis of anilines.
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