Gas-phase Smiles Rearrangement of Sulfonylurea Herbicides in Electrospray Ionization Mass Spectrometry

In the negative ion mode of electrospray ionization tandem mass spectrometry （ES1-MS/MS） of four sulfonyl- urea herbicides, Smiles rearrangements were observed in rimsulfuron and nicosulfuron. In the case of rimsulfuron, two competitive gas-phase Smiles rearrangements initiated by nitrogen anion and...

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Published inChinese journal of chemistry Vol. 30; no. 10; pp. 2383 - 2388
Main Author 张佳 柴云峰 王伟 尚伟 潘远江
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.10.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Herbicides
ion-neutral complex
Ionization
Ions
Mass spectrometry
Scientific imaging
Smiles rearrangement
sulfonylurea herbicides
反应中间体
密度泛函理论
气相
测定
电喷雾串联质谱
磺酰脲类除草剂
谱法
重排
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ISSN1001-604X
1614-7065
DOI10.1002/cjoc.201200610

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Summary:In the negative ion mode of electrospray ionization tandem mass spectrometry （ES1-MS/MS） of four sulfonyl- urea herbicides, Smiles rearrangements were observed in rimsulfuron and nicosulfuron. In the case of rimsulfuron, two competitive gas-phase Smiles rearrangements initiated by nitrogen anion and oxygen anion respectively were witnessed. The ion-neutral complex was proposed as the reactive intermediate in the course of this unimoleeular dissociation reaction of the oxygen attack Smiles rearrangement route. The density functional theory （DFT） was carried out to elucidate the mechanism as well as to show the possible transition states and the intermediates.
Bibliography:31-1547/O6
In the negative ion mode of electrospray ionization tandem mass spectrometry （ES1-MS/MS） of four sulfonyl- urea herbicides, Smiles rearrangements were observed in rimsulfuron and nicosulfuron. In the case of rimsulfuron, two competitive gas-phase Smiles rearrangements initiated by nitrogen anion and oxygen anion respectively were witnessed. The ion-neutral complex was proposed as the reactive intermediate in the course of this unimoleeular dissociation reaction of the oxygen attack Smiles rearrangement route. The density functional theory （DFT） was carried out to elucidate the mechanism as well as to show the possible transition states and the intermediates.
sulfonylurea herbicides, Smiles rearrangement, ion-neutral complex, mass spectrometry
Zhang, Jia Chai, Yunfeng Wang, Wei Shang, Wei Pan, Yuanjiang a Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China b Laprode （Zhejiang） Analysis Co., Ltd, Hangzhou, Zhejiang 310052, China
istex:CF80E4BC27198F5BF2CD2F52384E0EE2EF942FB5
ark:/67375/WNG-0DXG6G30-1
the National Natural Science Foundation of China - No. 21025207 and 20975092
ArticleID:CJOC201200610
ObjectType-Article-1
SourceType-Scholarly Journals-1
content type line 14
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201200610