Competitive Deprotonation and Superoxide [O2 -᾿/sup>] Radical-Anion Adduct Formation Reactions of Carboxamides under Negative-Ion Atmospheric-Pressure Helium-Plasma Ionization (HePI) Conditions

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• 作者：Isra Hassan ; Spencer Pinto ; Carl Weisbecker…
• 关键词：Helium ; plasma ionization (HePI) ; Carboxamides ; Superoxide radical anion ; Adducts
• 刊名：Journal of The American Society for Mass Spectrometry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：27
• 期：3
• 页码：394-401
• 全文大小：1,205 KB
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• 作者单位：Isra Hassan (1)
  Spencer Pinto (1)
  Carl Weisbecker (1)
  Athula B. Attygalle (1)
  
  1. Center for Mass Spectrometry, Department of Chemistry, Chemical Biology, and Biomedical Engineering, Stevens Institute of Technology, Hoboken, NJ, 07030, USA
  
• 刊物主题：Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
• 出版者：Springer US
• ISSN：1879-1123

文摘

Carboxamides bearing an N–H functionality are known to undergo deprotonation under negative-ion-generating mass spectrometric conditions. Herein, we report that N–H bearing carboxamides with acidities lower than that of the hydroperoxyl radical (HO-O•) preferentially form superoxide radical-anion (O₂ -•) adducts, rather than deprotonate, when they are exposed to the glow discharge of a helium-plasma ionization source. For example, the spectra of N-alkylacetamides show peaks for superoxide radical-anion (O₂ -•) adducts. Conversely, more acidic amides, such as N-alkyltrifluoroacetamides, preferentially undergo deprotonation under similar experimental conditions. Upon collisional activation, the O₂ -• adducts of N-alkylacetamides either lose the neutral amide or the hydroperoxyl radical (HO-O•) to generate the superoxide radical-anion (m/z 32) or the deprotonated amide [m/z (M – H)−], respectively. For somewhat acidic carboxamides, the association between the two entities is weak. Thus, upon mildest collisional activation, the adduct dissociates to eject the superoxide anion. Superoxide-adduct formation results are useful for structure determination purposes because carboxamides devoid of a N–H functionality undergo neither deprotonation nor adduct formation under HePI conditions.