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Unexpected mass spectral skeletal rearrangements in aromatic thioamides
Author(s) -
Ramana D. V.,
Viswanadham S. K.
Publication year - 1982
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.1210170904
Subject(s) - piperidine , mass spectrum , chemistry , morpholine , pyrrolidine , ion , spectral line , high resolution , stereochemistry , medicinal chemistry , organic chemistry , physics , remote sensing , astronomy , geology
Interesting skeletal rearrangements, resulting in the formation of unexpected fragments, have been noticed in the mass spectra of aromatic thioamides of cyclic amines such as piperidine, morpholine and pyrrolidine. Suitable mechanisms, based on mass analysed ion kinetic energy spectra, high voltage scan spectra and high resolution data, have been proposed for the formation of [MSH] + ions and the fragment at m / z (103+R) in the mass spectra of these compounds. The mass spectra of the thioamides of non‐cyclic amines and the thioamides of aliphatic acids contain peaks corresponding to a four‐centred skeletal rearrangement followed by the elimination of either the thioalkoxy or the thiophenoxy radical from the molecular ions.