Mass spectrometric study of aliphatic α‐carbonyl azides

Abstract

A series of derivatives of 2-azidoacetic acid and 2-azidoacetone were synthesized and their behaviour under electron ionization conditions was investigated. This paper reports the electron ionization fragmentation mechanisms for five aliphatic alpha-carbonyl azides, which were clarified by accurate mass measurements and B/E linked scans. The substituent influences the abundance and the nature of the ions resulting from the molecular ion fragmentation.

Electron ionization mass spectrometry in the characterization of azidonitriles

“…At first sight it was obvious that ions at m/z 28 were the most abundant for the azidopropionitriles and the second most abundant for azidoacetonitrile (Table 1). This observation suggests that thermal degradation was taking place before ionization, as was observed previously4 for the α ‐carbonyl azides. This conclusion was reinforced by the fact that no ion at m/z 28 was obtained as a product ion resulting from a metastable transition of the molecular ions (see below).…”

“…In spite of the wide range of applications, these compounds are highly unstable and thus their synthesis and characterization is not an easy task. Mass spectrometry has already proven to be a powerful technique for the structural characterization of these compounds 4,5. In earlier work,4 we studied the α ‐carbonyl azides using mass spectrometry techniques.…”

“…Mass spectrometry has already proven to be a powerful technique for the structural characterization of these compounds 4,5. In earlier work,4 we studied the α ‐carbonyl azides using mass spectrometry techniques. Now we have extended this work to the synthesis and study of the azidonitriles.…”

Complexation of transition metals by 3-azidopropionitrile. An electrospray ionization mass spectrometry study

“…An important feature in the reactivity of organoazides is the loss of molecular nitrogen, which can be induced thermally, photochemically,áorácatalyticallyábyáacidáorátransitionámetalsá [18á -20].áInáspiteáofátheiráinstability,ásomeáspectroscopic studies have been performed to monitor their decompositioná [21][22][23][24][25].áSomeáofátheáaliphaticáazidesáspectro-scopically investigated, such as, azidoacetic acid, azidoacetone, and azidonitriles, have been selected for studies of their decomposition on surfaces. So far, azidoacetic acid is the only aliphatic azide for which a surface study of its decomposition has been completed [26];ápreviously,áhydrazoicáacidáhadábeenáinvestigated asáaáprecursoráinásemiconductorápreparationá [27][28][29].…”

An electrospray ionization mass spectrometry study of azidoacetic acid/transition metal complexes

“…Azidoacetic acid was synthesized, purified and characterized as previously reported . Upon synthesis, azidoacetic acid was stored at dry ice temperature.…”