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Gas Phase Chemistry of Li+ with Amides: the Observation of LiOH Loss in Mass Spectrometry
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  • 作者：Cheng Guo (1)
    Yuping Zhou (1)
    Pengyuan Liu (1)
    Yunfeng Chai (1)
    Yuanjiang Pan (1)
  • 关键词：2 ; (4 ; 6 ; Dimethoxypyrimidin ; 2 ; ylsulfanyl) ; N ; phenylbenzamide ; N ; phenylbenzamide ; N ; phenylcinnamide ; LiOH loss ; H/D exchange ; Smiles rearrangement ; Theoretical calculation ; Substituent effect
  • 刊名：Journal of The American Society for Mass Spectrometry
  • 出版年：2012
  • 出版时间：July 2012
  • 年：2012
  • 卷：23
  • 期：7
  • 页码：1191-1201
  • 全文大小：698KB
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  • 作者单位：Cheng Guo (1)
    Yuping Zhou (1)
    Pengyuan Liu (1)
    Yunfeng Chai (1)
    Yuanjiang Pan (1)

    1. Department of Chemistry, Zhejiang University, Hangzhou, 310027, China
文摘
Collision-induced dissociation (CID) of Li+ adducts of three sets of compounds that contains an amide bond, including 2-(4, 6-dimethoxypyrimidin-2-ylsulfanyl)-N-phenylbenzamide, its derivatives and simpler structures was investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Observed fragment ions include those that reflect loss of LiOH. Other product ions result from the Smiles rearrangement and direct C–S bond cleavage. MS/MS of H/D exchange products demonstrated occurrence of a 1,3-H shift from the amide nitrogen atom to the phenyl ring of these compounds. The LiOH loss from Li+ adducts of amides was further examined by CID of [M + Li]+ ions of N-phenylbenzamide and N-phenylcinnamide. Loss of LiOH was essentially the sole fragmentation reaction observed for the former. For the latter, both losses of LiOH and H2O were discovered. The presence of electron-donating substituents of the phenyl ring of these compounds was found to facilitate elimination of LiOH, while that loss was retarded by electron-withdrawing substituents. Proposed fragment ion structures were supported by elemental compositions deduced from ultrahigh resolution Fourier transform ion cyclotron resonance tandem mass spectrometry (FTICR-MS/MS) m/z value determinations. Density functional theory-based (DFT) calculations were performed to evaluate potential mechanisms for these reactions.

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