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Ortho effects–I: Fragmentation mechanisms in some ortho-substituted nitroarenes
Authors:F. Benoit  J. L. Holmes
Abstract:The mass spectra of o-nitrobenzoic acid, o-nitroanisole, o-nitrosobenzoic acid, o-nitrobenzamide, o-nitrobenzyl alcohol and o-nitrosobenzaldehyde have been studied. Fragmentation mechanisms are proposed for the above compounds; their elucidation was aided by isotopic labeling with D and O18. Two ‘ortho-effects’ are discussed; one involving H atom transfer between substituents and the other migration of an atom or group to a charge carrying vacant ortho position. The importance of nitro to nitrite conversion in molecular and fragment ions is discussed.
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