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

✍ Scribed by N. M. M. Nibbering; Th. J. De Boer

• Publisher: John Wiley and Sons
• Year: 1970
• Tongue: English
• Weight: 863 KB
• Volume: 3
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/oms.1210030407

✦ Synopsis

Abstract

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.