Abstract
A previously unreported series of N-(substituted benzalamino)phthalimides was investigated by using the combined techniques of high resolution electron ionization mass spectrometry, metastable decomposition, and collisional activation mass spectrometry. The predominate fragmentation pathway is a McLafferty-type rearrangement. There also occurs, to a lesser extent, a transfer of hydrogen that originates from a substituent remote from the phthalimide moiety and terminates on the phthalimide, The process is interpreted as proceeding via an ion-neutral complex. The effects of substituents on both of the aforementioned fragmentation pathways provide a striking example that gives quantitative evidence for Stevenson’s rule. The substituent effects are responsible for a trend in ion abundance that shows a sharp reversal at approximately the ionization energy of the iminium isomer of the phthalimide molecular ion.
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Jacoby, C.B., Gross, M.L. & Zey, R.L. The decompositions of N-(substituted benzalamino)phthalimide radical cations embody ion-neutral complexes and Stevenson’s rule. J. Am. Soc. Spectrom. 5, 837–844 (1994). https://doi.org/10.1016/1044-0305(94)87006-3
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DOI: https://doi.org/10.1016/1044-0305(94)87006-3