The Mass Spectrometry society of Japan - The 68th Annual Conference on Mass Spectrometry, Japan
Japanese

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Day 3, May 13（Wed.）　　Poster (1008/09)

3P-32　　PDF

Long-Distance Proton Transfer Induced by a Single Ammonia Molecule: Ion Mobility Mass Spectrometry of Protonated Benzocaine Reacted with NH3

(Tohoku Univ.)
Shun Miyazaki, Keigo Hattori, oKeijiro Ohshimo, Fuminori Misaizu

Using ion mobility mass spectrometry, we obtained an experimental evidence that intramolecular proton transfer between two structural isomers with different protonation sites of protonated benzocaine (BC) is induced by a single NH3 molecule. In combination with theoretical calculations of the reaction path search, it was concluded that intramolecular proton transfer to produce the O-protomer (protonated BC at the C=O group) proceeds in the N-protomer (protonated BC at the NH2 group) by NH3 coordination. In the calculated pathway, the NH4+ ion formed by proton transfer from the NH2 group of the N-protomer to NH3 donates a proton to the C=O group after hopping on the benzene ring of BC.