Literature DB >> 26926444

Decarboxylative Coupling Reaction in ESI(-)-MS/MS of 4-Nitrobenzyl 4-Hydroxybenzoates: Triplet Ion-Neutral Complex-Mediated 4-Nitrobenzyl Transfer.

Xiaoping Zhang1,2, Xingfeng Bai1, Liwen Fang1, Kezhi Jiang3, Zuguang Li4.   

Abstract

In negative electrospray ionization mass spectrometry of 4-nitrobenzyl 4-hydroxybenzoates, a decarboxylation reaction, which was significantly promoted by the presence of a nitro group on the benzyl group, competed with radical elimination reactions. Density functional theory calculations indicated that decarboxylation of deprotonated 4-nitrobenzyl vanillate occurred via a radical route involving homolytic cleavage of the Cbenzyl-O bond to give a triplet ion-neutral complex, followed by decarboxylative coupling.

Entities:  

Keywords:  Decarboxylative coupling; MS/MS; Nitrobenzyl transfer; Nitrobenzyl vanillates; Triplet ion-neutral complex

Year:  2016        PMID： 26926444     DOI： 10.1007/s13361-016-1339-7

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN： 1044-0305            Impact factor:   3.109


  17 in total

1.  Intramolecular charge transfer in the gas phase: fragmentation of protonated sulfonamides in mass spectrometry.

Authors:  Nan Hu; Ya-Ping Tu; Kezhi Jiang; Yuanjiang Pan
Journal:  J Org Chem       Date:  2010-06-18       Impact factor: 4.354

Review 2.  Selected patented cross-coupling reaction technologies.

Authors:  Jean-Pierre Corbet; Gérard Mignani
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  The competing radical eliminations in the tandem mass spectrometry of the OH-deprotonated benzyl vanillate.

Authors:  Xiaoping Zhang; Peixi Zhu; Huarong Zhang; Zuguang Li; Kezhi Jiang; Maw-Rong Lee
Journal:  J Mass Spectrom       Date:  2015-02       Impact factor: 1.982

4.  Gas-phase chemistry of benzyl cations in dissociation of N-benzylammonium and N-benzyliminium ions studied by mass spectrometry.

Authors:  Yunfeng Chai; Lin Wang; Hezhi Sun; Cheng Guo; Yuanjiang Pan
Journal:  J Am Soc Mass Spectrom       Date:  2012-02-25       Impact factor: 3.109

5.  Dissociative benzyl cation transfer versus proton transfer: loss of benzene from protonated N-benzylaniline.

Authors:  Hezhi Sun; Yunfeng Chai; Yuanjiang Pan
Journal:  J Org Chem       Date:  2012-07-31       Impact factor: 4.354

6.  Proteolytic 18O labeling for comparative proteomics: model studies with two serotypes of adenovirus.

Authors:  X Yao; A Freas; J Ramirez; P A Demirev; C Fenselau
Journal:  Anal Chem       Date:  2001-07-01       Impact factor: 6.986

7.  An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines.

Authors:  Jason Bialecki; Josef Ruzicka; Athula B Attygalle
Journal:  J Mass Spectrom       Date:  2006-09       Impact factor: 1.982

8.  Homolytic cleavages in pyridinium ions, an excited state process.

Authors:  Chagit Denekamp; Elena Tenetov; Yonit Horev
Journal:  J Am Soc Mass Spectrom       Date:  2003-07       Impact factor: 3.109

9.  Gas-phase fragmentation of the protonated benzyl ester of proline: intramolecular electrophilic substitution versus hydride transfer.

Authors:  Fei Li; Xiaoping Zhang; Huarong Zhang; Kezhi Jiang
Journal:  J Mass Spectrom       Date:  2013-04       Impact factor: 1.982

10.  Methyl group migration during the fragmentation of singly charged ions of trimethyllysine-containing peptides: precaution of using MS/MS of singly charged ions for interrogating peptide methylation.

Authors:  Lei Xiong; Liyan Ping; Bifeng Yuan; Yinsheng Wang
Journal:  J Am Soc Mass Spectrom       Date:  2009-02-13       Impact factor: 3.109
View more
  2 in total

1.  Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CH3OH and CH3O-P=O from Protonated Phosphorothioates.

Authors:  Xiaoping Zhang; Honghan Chen; Yin Ji; Kezhi Jiang; Huanwen Chen
Journal:  J Am Soc Mass Spectrom       Date:  2018-12-19       Impact factor: 3.109

2.  Intramolecular Halogen Atom Coordinated H Transfer via Ion-Neutral Complex in the Gas Phase Dissociation of Protonated Dichlorvos Derivatives.

Authors:  Xiaoping Zhang; Shuai Cheng
Journal:  J Am Soc Mass Spectrom       Date:  2017-07-05       Impact factor: 3.109
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.