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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
Wang HY(王昊阳); Zhang X(张祥); Guo YL(郭寅龙); Tang QH(唐庆红); Lv L(吕龙)
2006
发表期刊J. Am. Soc. Mass Spectrom.
ISSN1044-0305
卷号17期号:2页码:253-263
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.
学科领域分析化学
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
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收录类别SCI
语种英语
WOS记录号WOS:000235378700017
引用统计
被引频次:35[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/19928
专题分析化学研究室
通讯作者Guo YL(郭寅龙); Lv L(吕龙)
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GB/T 7714
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.
APA 王昊阳,张祥,郭寅龙,唐庆红,&吕龙.(2006).Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution.J. Am. Soc. Mass Spectrom.,17(2),253-263.
MLA 王昊阳,et al."Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution".J. Am. Soc. Mass Spectrom. 17.2(2006):253-263.
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