Gas-phase reaction: alkyl cation transfer in the dissociation of protonated pyridyl carbamates in mass-spectrometry

被引：13

作者：

Yue, Lei ^{[1
]}

Guo, Cheng ^{[2
]}

Chai, Yunfeng ^{[1
]}

Yin, Xinchi ^{[1
]}

Pan, Yuanjiang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Zhejiang Univ, Affiliated Hosp 2, Sch Med, Inst Canc, Hangzhou 310009, Zhejiang, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 50期

基金：

中国国家自然科学基金;

关键词：

Proton transfer; Alkyl cation transfer; Collision induced dissociation; Pyridyl carbamate; Ion-neutral complex; DFT calculation; ION-NEUTRAL COMPLEXES; METHYL-TRANSFER-REACTIONS; DIMETHYLCHLORINIUM ION; INTERNAL REACTIONS; BOND-CLEAVAGE; PI-COMPLEXES; FRAGMENTATION; PEPTIDE; MOLECULES; BENZALDEHYDES;

D O I：

10.1016/j.tet.2014.10.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the mass spectrometry of pyridyl carbamates, alkyl cation transfer is one of the major fragmentation reactions of the protonated molecules. Literature results and theoretical calculations indicate that the pyridine nitrogen is the most favorable site for protonation in these structures. Substituent and comparison experiments run to elucidate the fragmentation patterns reveal that the proton is localized at the pyridine nitrogen and the reaction center is charge-remote when the alkyl cation transfer occurs. The mechanism involving configuration inversion via an ion-neutral complex is favorable in energy for the alkyl cation transfer in these structures. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9500 / 9505

页数：6

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