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Ortho effects in organic molecules on electron impact. 14—Concerted and stepwise ejections of SO 2 and N 2 from N ‐arylidene 2‐nitrobenzenesulphenamides
Author(s) -
Ramana D. V.,
Sundaram N.,
George M.
Publication year - 1987
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.1210220305
Subject(s) - substituent , mass spectrum , ion , chemistry , electron ionization , molecule , nitro , medicinal chemistry , organic chemistry , alkyl , ionization
Unexpected ortho interaction of the nitro group has been noticed during the mass spectral fragmentations of N ‐arylidene 2‐nitrobenzenesulphenamides, where the molecular ions expel SO 2 and N 2 both in concerted and stepwise processes. Loss of a hydrogen or the substituent from this fragment leads to a very abundant ion in all the compounds studied. Based on chemical evidence and linked‐scan studies, a 1,2‐phenylenetropylium cation structure has been postulated for the [M–SO 2 –N 2 –H/substituent] + ion.