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学科主题: 分析化学
题名: Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution
其他题名: 串级质谱法预测溶液中2-嘧啶氧基-N-芳基苄胺类衍生物的化学结构转化
作者: Wang HY(王昊阳) ; Zhang X(张祥) ; Guo YL(郭寅龙) ; Tang QH(唐庆红) ; Lv L(吕龙)
通讯作者: 郭寅龙 ; 吕龙
刊名: J. Am. Soc. Mass Spectrom.
发表日期: 2006
卷: 17, 期:2, 页:253-263
收录类别: SCI
部门归属: 上海有机所上海质谱中心; 上海有机所有机氟化学重点实验室
英文摘要: Tandem mass spectrometry is used to predict the chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives. Compound 1, N-2-2-4,6- dimethoxypyrimidin-2-yloxy benzylamino phenyl benzamide was selected as a model to present our idea. The CID reactions of protonated 1 include an intramolecular S(N)2 reaction and a cyclodehydration reaction. Under in-source CID conditions, deprotonated 1 undergoes a Smiles rearrangement reaction and then dissociates to the ion at m/z 349. Theoretical computations were invoked to shed light on the reaction mechanisms of 1 by the semiempirical PM3 method. These studies of gas-phase reactions show the reactivity of some potential reaction centers in this molecule, which inspired us to explore the solution phase analogous reactions of 1. Further experiments show that 1 has two analogous reactions in acidic solution: the acid-catalyzed cyclodehydration reaction and the acid-catalyzed Smiles rearrangement reaction. Moreover, I undergoes the base-catalyzed Smiles rearrangement under basic conditions. The present study demonstrates that mass spectrometry can play an important role in predicting the chemical solution phase transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives.
语种: 英语
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WOS记录号: WOS:000235378700017
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19928
Appears in Collections:分析化学研究室_期刊论文

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Recommended Citation:
Wang HY,Zhang X,Guo YL,et al. Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution[J]. J. Am. Soc. Mass Spectrom.,2006,17(2):253-263.
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