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• W2008103870 abstract "In mass spectrometry of protonated N-benzylbutyrolactams, the added proton is initially localized on the carbonyl oxygen, which is the thermodynamically preferred protonation site. Upon collisional activation, dissociative proton transfer takes place leading to the occurrence of fragmentation reactions. The major fragmentations observed are the cleavages of Cα–Cβ and Cα–N bonds on the two sides of the methylene linker, which is different to the cleavage of the amide bond itself seen in most amide cases. Theoretical calculations and isotopic labeling experiments demonstrate that the phenyl ring regulates the proton transfer reactions. The proton directly migrates to the Cβ position via a 1,5-H shift leading to the efficient loss of benzene, while it stepwise migrates to the amide nitrogen resulting in the formation of a benzyl cation. The stepwise proton transfer is achieved via intramolecular proton-transport catalysis. The Cγ position accepts the proton from the carbonyl oxygenvia a 1,6-H shift, and then donates it to the amide nitrogenvia a 1,4-H shift. The general 1,3-H shift from the carbonyl oxygen to the amide nitrogen can be excluded in this case due to its significant energy barrier. The substituent effects are also applied to explore the reaction mechanism, and it proves that both Cβ and Cγ are involved in the dissociative proton transfer processes. For monosubstituted N-benzylbutyrolactams, the abundance ratios of the two competing product ions are well correlated with the nature of the substituents." @default.
• W2008103870 created "2016-06-24" @default.
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• W2008103870 date "2012-01-01" @default.
• W2008103870 modified "2023-09-22" @default.
• W2008103870 title "C^α–C^βand C^α–N bond cleavage in the dissociation of protonated N–benzyllactams: dissociative proton transfer and intramolecular proton-transport catalysis" @default.
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• W2008103870 doi "https://doi.org/10.1039/c1ob06020a" @default.
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