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Rearrangements in the mass spectra of α‐phenylcinnamic acid and its derivatives
Author(s) -
Madhusudanan K. P.,
Murthy V. S.,
Fraisse D.,
Becchi M.
Publication year - 1991
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210260525
Subject(s) - mass spectrum , fragmentation (computing) , chemistry , electron ionization , trimethylsilyl , cinnamic acid , polyatomic ion , ion , spectral line , molecule , stereochemistry , hydrogen , ionization , medicinal chemistry , physics , organic chemistry , astronomy , computer science , operating system
The electron impact ionization and collisional activation mass spectra of α‐phenylcinnamic acid and its derivatives have been studied. The loss of a phenylic hydrogen is not an important process in these molecules, unlike the unsubstituted cinnamic acids. However, in o ‐chloro‐α‐phenylcinnamic acid and its methyl and trimethylsilyl derivatives loss of Cl resulting in the formation of 2‐substituted‐3‐phenylbenzopyrilium ion is an important fragmentation pathway. The rearrangement ions observed at m / z 118 and 107 in the Spectrum of α‐phenylcinnamic acid have been found to have the structures of the M + ˙ of benzofuran and PhCH \documentclass{article}\pagestyle{empty}\begin{document}$ \mathop {\rm O}\limits^{\rm +} $\end{document} H, respectively. The ion at m / z 121 in the spectrum of the methyl ester of α‐phenylcinnamic acid has been found to have the structure PhCH \documentclass{article}\pagestyle{empty}\begin{document}$ \mathop {\rm O}\limits^{\rm +} $\end{document} Me.