Mass spectrometric studies of the gas phase retro-Michael type fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives

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	Mass spectrometric studies of the gas phase retro-Michael type fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives
	Wang HY(王昊阳) ; Zhang X(张祥) ; Guo YL(郭寅龙) ; Dong XC(董喜城) ; Tang QH(唐庆红) ; Lv L(吕龙)
刊名	J. Am. Soc. Mass Spectrom.
	2005
卷号	16 期号:9 页码:1561-1573
ISSN号	1044-0305
其他题名	气相中苯磺酰胺键的断裂以及随后的对氨基磺酰基正离子的重排反应：应用于研究2-嘧啶氧基-苄胺-苯磺酰胺除草剂
通讯作者	郭寅龙
英文摘要	The gas-phase fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives (Compounds I to 6), the O-N-type acid-catalyzed Smiles rearrangement products of 2-pyrimidinyloxy-N-arylbenzylamine derivatives, have been examined via positive ion matrix-assisted laser desorption/ionization (MALDI) infrared multiphoton dissociation (IRMPD) mass spectrometry in FT-ICR MS and via negative ion electrospray ionization (ESI) in-source collision-induced dissociation (CID) mass spectrometry, respectively. The major fragmentation pathway of protonated 1 to 6 gives the F ions under IRMPD; theoretical results show that the retro-Michael reaction channel is more favorable in both thermodynamics and kinetics. This explanation is supported by H/D exchange experiments and the MS/MS experiment of acetylated 1. Deprotonated I to 6 give rise to the solitary E ions (aromatic nitrogen anions) in the negative ion in-source CID; theoretical calculations show that a retro-Michael mechanism is more reasonable than a gas-phase intramolecular nucleophilic displacement (S(N)2) mechanism to explain this reaction process. (c) 2005 American Society for Mass Spectrometry.
学科主题	有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1016/j.jasms.2005.05.006
语种	英语
WOS记录号	WOS:000231646500018
公开日期	2013-02-25
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/19886]
专题	上海有机化学研究所_分析化学研究室
推荐引用方式 GB/T 7714	Wang HY,Zhang X,Guo YL,et al. Mass spectrometric studies of the gas phase retro-Michael type fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives[J]. J. Am. Soc. Mass Spectrom.,2005,16(9):1561-1573.
APA	王昊阳,张祥,郭寅龙,董喜城,唐庆红,&吕龙.(2005).Mass spectrometric studies of the gas phase retro-Michael type fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives.J. Am. Soc. Mass Spectrom.,16(9),1561-1573.
MLA	王昊阳,et al."Mass spectrometric studies of the gas phase retro-Michael type fragmentation reactions of 2-hydroxybenzyl-N-pyrimidinylamine derivatives".J. Am. Soc. Mass Spectrom. 16.9(2005):1561-1573.