Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation

Abstract This paper reports on the gas-phase amination reaction of aromatic hydrocarbons occurring under corona discharge conditions with N2 gas as the nitrogen source. The corona discharge device within an atmospheric pressure chemical ionization source was employed to achieve the plasma-assisted N...

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Autores principales:	Shanshan Shen, Yunfeng Chai, Qirong Shen, You Jiang, Xiang Fang, Yuanjiang Pan
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/7b56e9a36c6c4780825b84ffbaf13213
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spelling	oai:doaj.org-article:7b56e9a36c6c4780825b84ffbaf132132021-12-02T14:06:11ZGas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation10.1038/s41598-021-82190-82045-2322https://doaj.org/article/7b56e9a36c6c4780825b84ffbaf132132021-02-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-82190-8https://doaj.org/toc/2045-2322Abstract This paper reports on the gas-phase amination reaction of aromatic hydrocarbons occurring under corona discharge conditions with N2 gas as the nitrogen source. The corona discharge device within an atmospheric pressure chemical ionization source was employed to achieve the plasma-assisted N2 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, N2 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.Shanshan ShenYunfeng ChaiQirong ShenYou JiangXiang FangYuanjiang PanNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-9 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Shanshan Shen Yunfeng Chai Qirong Shen You Jiang Xiang Fang Yuanjiang Pan Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
description	Abstract This paper reports on the gas-phase amination reaction of aromatic hydrocarbons occurring under corona discharge conditions with N2 gas as the nitrogen source. The corona discharge device within an atmospheric pressure chemical ionization source was employed to achieve the plasma-assisted N2 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, N2 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.
format	article
author	Shanshan Shen Yunfeng Chai Qirong Shen You Jiang Xiang Fang Yuanjiang Pan
author_facet	Shanshan Shen Yunfeng Chai Qirong Shen You Jiang Xiang Fang Yuanjiang Pan
author_sort	Shanshan Shen
title	Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
title_short	Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
title_full	Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
title_fullStr	Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
title_full_unstemmed	Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
title_sort	gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/7b56e9a36c6c4780825b84ffbaf13213
work_keys_str_mv	AT shanshanshen gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation AT yunfengchai gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation AT qirongshen gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation AT youjiang gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation AT xiangfang gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation AT yuanjiangpan gasphaseaminationofaromatichydrocarbonsbycoronadischargeassistednitrogenfixation
_version_	1718392029208117248

Gas-phase amination of aromatic hydrocarbons by corona discharge-assisted nitrogen fixation

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