苯甲酰苯胺质谱中的邻近效应。

IF 1.1 4区 化学 Q4 PHYSICS, ATOMIC, MOLECULAR & CHEMICAL
Nathan W Fenwick, Amie Saidykhan, Yasser Nazir, Richard Telford, Binyaameen Masood, William H C Martin, Richard T Gallagher, Richard D Bowen
{"title":"苯甲酰苯胺质谱中的邻近效应。","authors":"Nathan W Fenwick,&nbsp;Amie Saidykhan,&nbsp;Yasser Nazir,&nbsp;Richard Telford,&nbsp;Binyaameen Masood,&nbsp;William H C Martin,&nbsp;Richard T Gallagher,&nbsp;Richard D Bowen","doi":"10.1177/14690667211054152","DOIUrl":null,"url":null,"abstract":"<p><p>The analytical value of peaks arising by a proximity effect in the electron ionization mass spectra of benzanilides has been established by examining the spectra of numerous examples of general structure XC<sub>6</sub>H<sub>4</sub>NHCOC<sub>6</sub>H<sub>4</sub>Y. Significant [M-X]<sup>+</sup> signals are observed only when X = Cl, Br, I or CH<sub>3</sub>O in the 2-position. The presence of strong [M-X]<sup>+</sup> signals, but negligibly weak [M-Y]<sup>+</sup> peaks, even when the C-Y bond would be expected to break more readily than the C-X bond, indicates that these diagnostically useful signals do not arise by simple cleavage. Similarly, the presence of an appreciable [M-Cl]<sup>+</sup> signal, but no [M-Br]<sup>+</sup> signal, in the spectra of representative examples of 4-Br-2ClC<sub>6</sub>H<sub>3</sub>NHCOC<sub>6</sub>H<sub>4</sub>Y, reveals that loss of a substituent from the 2-position occurs much more rapidly than fission of a weaker bond to a substituent in the 4-position. These trends are interpreted in terms of cyclization of the ionized 2-substituted benzanilide, followed by elimination of the substituent originally in the 2-position, to form a protonated 2-arylbenzoxazole.</p>","PeriodicalId":12007,"journal":{"name":"European Journal of Mass Spectrometry","volume":null,"pages":null},"PeriodicalIF":1.1000,"publicationDate":"2021-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/b1/ba/10.1177_14690667211054152.PMC8586190.pdf","citationCount":"1","resultStr":"{\"title\":\"Proximity Effects in Mass Spectra of Benzanilides.\",\"authors\":\"Nathan W Fenwick,&nbsp;Amie Saidykhan,&nbsp;Yasser Nazir,&nbsp;Richard Telford,&nbsp;Binyaameen Masood,&nbsp;William H C Martin,&nbsp;Richard T Gallagher,&nbsp;Richard D Bowen\",\"doi\":\"10.1177/14690667211054152\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The analytical value of peaks arising by a proximity effect in the electron ionization mass spectra of benzanilides has been established by examining the spectra of numerous examples of general structure XC<sub>6</sub>H<sub>4</sub>NHCOC<sub>6</sub>H<sub>4</sub>Y. Significant [M-X]<sup>+</sup> signals are observed only when X = Cl, Br, I or CH<sub>3</sub>O in the 2-position. The presence of strong [M-X]<sup>+</sup> signals, but negligibly weak [M-Y]<sup>+</sup> peaks, even when the C-Y bond would be expected to break more readily than the C-X bond, indicates that these diagnostically useful signals do not arise by simple cleavage. Similarly, the presence of an appreciable [M-Cl]<sup>+</sup> signal, but no [M-Br]<sup>+</sup> signal, in the spectra of representative examples of 4-Br-2ClC<sub>6</sub>H<sub>3</sub>NHCOC<sub>6</sub>H<sub>4</sub>Y, reveals that loss of a substituent from the 2-position occurs much more rapidly than fission of a weaker bond to a substituent in the 4-position. These trends are interpreted in terms of cyclization of the ionized 2-substituted benzanilide, followed by elimination of the substituent originally in the 2-position, to form a protonated 2-arylbenzoxazole.</p>\",\"PeriodicalId\":12007,\"journal\":{\"name\":\"European Journal of Mass Spectrometry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.1000,\"publicationDate\":\"2021-10-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/b1/ba/10.1177_14690667211054152.PMC8586190.pdf\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Mass Spectrometry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1177/14690667211054152\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"PHYSICS, ATOMIC, MOLECULAR & CHEMICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Mass Spectrometry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1177/14690667211054152","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"PHYSICS, ATOMIC, MOLECULAR & CHEMICAL","Score":null,"Total":0}
引用次数: 1

摘要

通过对一般结构XC6H4NHCOC6H4Y的谱分析,确定了苯甲苯胺电子电离质谱中由邻近效应引起的峰的分析值。只有当X = Cl、Br、I或ch30在2位时,才观察到显著的[M-X]+信号。强[M-X]+信号的存在,但可忽略的弱[M-Y]+峰,即使当C-Y键比C-X键更容易断裂时,表明这些诊断有用的信号不是由简单的裂解产生的。同样,在代表性的4-Br-2ClC6H3NHCOC6H4Y的光谱中,存在明显的[M-Cl]+信号,但没有[M-Br]+信号,这表明取代基从2位的损失比弱键到4位取代基的裂变要快得多。这些趋势可以解释为电离的2-取代苯并苯胺的环化,然后消除原来在2位的取代基,形成质子化的2-芳基苯并恶唑。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Proximity Effects in Mass Spectra of Benzanilides.

Proximity Effects in Mass Spectra of Benzanilides.

Proximity Effects in Mass Spectra of Benzanilides.

Proximity Effects in Mass Spectra of Benzanilides.

The analytical value of peaks arising by a proximity effect in the electron ionization mass spectra of benzanilides has been established by examining the spectra of numerous examples of general structure XC6H4NHCOC6H4Y. Significant [M-X]+ signals are observed only when X = Cl, Br, I or CH3O in the 2-position. The presence of strong [M-X]+ signals, but negligibly weak [M-Y]+ peaks, even when the C-Y bond would be expected to break more readily than the C-X bond, indicates that these diagnostically useful signals do not arise by simple cleavage. Similarly, the presence of an appreciable [M-Cl]+ signal, but no [M-Br]+ signal, in the spectra of representative examples of 4-Br-2ClC6H3NHCOC6H4Y, reveals that loss of a substituent from the 2-position occurs much more rapidly than fission of a weaker bond to a substituent in the 4-position. These trends are interpreted in terms of cyclization of the ionized 2-substituted benzanilide, followed by elimination of the substituent originally in the 2-position, to form a protonated 2-arylbenzoxazole.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
2.40
自引率
7.70%
发文量
16
审稿时长
>12 weeks
期刊介绍: JMS - European Journal of Mass Spectrometry, is a peer-reviewed journal, devoted to the publication of innovative research in mass spectrometry. Articles in the journal come from proteomics, metabolomics, petroleomics and other areas developing under the umbrella of the “omic revolution”.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信