>In electrospray ionization tandem mass spectrometry of protonated 1‐benzoylamines (1‐benzoylpiperadine, 1‐benzoylmorpholine, and '/> Loss of benzaldehyde in the fragmentation of protonated benzoylamines: Benzoyl cation as a hydride acceptor in the gas phase
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首页> 外文期刊>Journal of mass spectrometry: JMS >Loss of benzaldehyde in the fragmentation of protonated benzoylamines: Benzoyl cation as a hydride acceptor in the gas phase
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Loss of benzaldehyde in the fragmentation of protonated benzoylamines: Benzoyl cation as a hydride acceptor in the gas phase

机译：在质子苯甲酰芳基胺的碎片中失去苯甲醛：苯甲酰基作为气相中的氢化物受体

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>In electrospray ionization tandem mass spectrometry of protonated 1‐benzoylamines (1‐benzoylpiperadine, 1‐benzoylmorpholine, and 1‐benzoyl‐4‐methylpiperazine), the dominant fragmentation pathway was amide bond cleavage to form benzoyl cation and neutral amine. Meanwhile, in their fragmentations, an interesting loss of benzaldehyde (106?Da) was observed and identified to derive from hydride transfer reaction between the benzoyl cation and amine. A stepwise mechanism for loss of 106?Da (benzene and CO) could be excluded with the aid of deuterium labeling experiment. Theoretical calculations indicated that hydride transfers from amines (piperadine, morpholine, and 1‐methylpiperazine) to benzoyl cation were thermodynamically permitted, and 1‐methylpiperazine was the best hydride donor among the 3 amines. The mass spectrometric experimental results were consistent with the computational results. The relative abundance of the iminium cation (relative to the benzoyl cation) in the fragmentation of protonated 1‐benzoyl‐4‐methylpiperazine was higher than that in the fragmentation of the other 2 protonated 1‐benzoylamines. By comparing the fragmentations of protonated 1‐benzyl‐4‐methylpiperazine and protonated 1‐benzoyl‐4‐methylpiperazine and the energetics of their hydride transfer reactions, this study revealed that benzoyl cation was a hydride acceptor in the gas phase, but which was weaker than benzyl cation.
机译： >在电喷雾电离串联1-苯甲酰胺的电离串联质谱（1-苯甲酰吡啶，1-苯甲酰卟啉和1 -Benzoyl-4-甲基哌嗪），优势碎裂途径是酰胺键切割，形成苯甲酰基阳离子和中性胺。同时，在碎片中，观察到苯甲醛（106〜DA）的有趣丧失，并鉴定出苯甲酰阳离子和胺之间的氢化物转移反应。借助于氘标记实验，可以排除损失106〜Da（苯和CO）的逐步机制。理论计算表明，热力学允许从胺（哌啶，吗啉和1-甲基哌嗪）与苯甲酰基阳离子的氢化物转移，1-甲基哌嗪是3胺中最好的氢化物供体。质谱实验结果与计算结果一致。在质子化1-苯甲酰基-4-甲基哌嗪的碎裂中（相对于苯甲酰阳离子相对于苯甲酰阳离子）的相对丰度高于另一个质子化1-苯甲酰胺的碎裂中的碎裂。通过比较质子化1-苄基-4-甲基哌嗪和质子化1-苯甲酰基-4-甲基哌嗪的碎片和它们的氢化物转移反应的能量学，揭示了苯甲酰阳离子在气相中是氢化物受体，但较弱比苄基阳离子。

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