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Vol. 26 No. 1 (2014): Vol 26 Issue 1

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Coordination-Mediated Radical Nitration of Methyl Salicylate by Ferric Nitrate

https://doi.org/10.14233/ajchem.2014.15819
Yanzhu Liu
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China ;Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Mingming Zu
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China
Xiuxin Zou
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China ;Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Qing Zheng
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China ;Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Xia Li
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China ;Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Xuezhen Zhou
Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Qun Tang
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China; Institute of Advanced Study, Nanchang University, Nanchang 330031, P.R. China
Shihan Zhang
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China; Institute of Advanced Study, Nanchang University, Nanchang 330031, P.R. China
Ling Zhang
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China; Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China
Yongxiu Li
Research Center for Rare Earths & Micro/Nano Functional Materials, Nanchang University, Nanchang 330031, P.R. China; Department of Chemistry, Nanchang University, Nanchang 330031, P.R. China ;Institute of Advanced Study, Nanchang University, Nanchang 330031, P.R. China

Corresponding Author(s) : Yongxiu Li

yxli@ncu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 1 (2014): Vol 26 Issue 1

Abstract

Nitration of methyl salicylate was performed by ferric nitrate in refluxing ethyl acetate solution. A coordination-mediated radical nitration process was proposed based on the results of electronic absorption spectra, cyclic voltammetry and electrospray ionization mass spectra. It was the coordination of methyl salicylate with ferric nitrate that promoted the splitting of N-O bonds of nitrate group in ferric nitrate and resulted in the formation of nitro radicals, oxygen radicals and complex radicals. The nitro radicals reacted with methyl salicylate or its complexes with iron to give a series of nitration products and Fe(II) ions. Meanwhile, oxygen radicals hydrolyzed to hydroxide which precipitated free ferric ions to isolate solid ferric oxides.

Keywords

Methyl salicylate Ferric nitrate Coordination Radicals Nitration
Liu, Y., Zu, M., Zou, X., Zheng, Q., Li, X., Zhou, X., … Li, Y. (2013). Coordination-Mediated Radical Nitration of Methyl Salicylate by Ferric Nitrate. Asian Journal of Chemistry, 26(1), 241–246. https://doi.org/10.14233/ajchem.2014.15819
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