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Mass spectrometry of aralkyl compounds with a functional group—VIII: Comparison of the breakdown of 3‐phenylnitropropane with that of 3‐phenylpropyl nitrite upon electron‐impact
Author(s) -
Nibbering N. M. M.,
De Boer Th. J.
Publication year - 1970
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.1210030407
Subject(s) - chemistry , nitrite , isomerization , molecule , mass spectrum , deuterium , polyatomic ion , ion , mass spectrometry , nitro , nitric oxide , fast atom bombardment , hydrogen atom , electron ionization , inorganic chemistry , group (periodic table) , organic chemistry , catalysis , alkyl , nitrate , chromatography , ionization , physics , quantum mechanics
Mass spectra of 3‐phenylnitropropane and of its analogues, specifically deuterated in the aliphatic chain and in the phenyl ring, show that the molecular ion loses a molecule of water in two different modes, viz. either with both α‐hydrogen atoms or with a γ‐ and an ortho ‐hydrogen atom. Moreover, a molecule of nitric oxide is eliminated from the molecular ion and the resulting [M ‐ NO] + ‐ion appears to decompose further in many complicated ways. This loss of nitric oxide does not arise from an isomerization of the nitro group to a nitrite group, because the [M ‐ NO] + ‐ion of 3‐phenylpropyl nitrite breaks down in an altogether different manner than that of 3‐phenylnitropropane. This is demonstrated by the spectra of specifically deuterated analogues of 3‐phenylpropyl nitrite.