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Fragmentation studies of pentacoordinated bisaminoacylspirophosphoranes by negative electrospray ionization mass spectrometry

✍ Scribed by Shuxia Cao; Yanchun Guo; Xinshuai Wu; Huamin Zhao; Yufen Zhao

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
234 KB
Volume
46
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

Fragmentation pathways of a series of pentacoordinated bisaminoacylspirophosphoranes were elucidated by electrospray ionization multistage mass spectrometry (ESI‐MS^n^) in negative mode. The deprotonated ions of pentacoordinated bisaminoacylspirophosphoranes tend to eliminate a corresponding amino acid to form base peak. The hydrogen/deuterium exchange experiment, the high‐resolution mass spectrometry, ^13^C stable isotope labeling experiment and theoretical calculations were used to rationalize the proposed fragmentation pathways and to verify the differences between the fragmentation pathways. The results indicate that the negative molecular ions of pentacoordinated bisaminoacylspirophosphoranes dissociate through its open‐chain tricoordinated tautomers. The relative Gibbs free energies (Δ__G__) of the product ions and proposed fragmentation pathways were estimated using the B3LYP/6‐31 + + G(d, p) model. The results have some potential applications in the identification structures of similar spirophosphorane compounds by ESI‐MS^n^. Copyright © 2011 John Wiley & Sons, Ltd.

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