Collision-Induced Dissociation of Imidazolium-Based Zwitterionic Liquids

Abstract

Fragmentation pathways of some imidazolium based zwitterionic liquids-3-(3-alkyl-1-imidazolio)- propane sulfonates and 3-(2-methyl-3-alkyl-1-imidazolio)-propane sulfonates -- have been studied by tandem electrospray mass spectrometry and collision-induced dissociation. The relative abundances of the lowest energy fragment ions depend on the length of the alkyl chain at the (II)N of the imidazolium ring and the cone voltage. The first fragment ions originate from the scission of C(non aromatic)-N bond of compounds investigated, but with increasing collision energy, scission of C-C bonds occurs. Aggregates of the general formula [(M + H)(x) + (M)(y)](+) (x;y = 1-2) formed. Methyl substituted zwitterionic liquids show higher molecular stability than 3-(3-alkyl-1-imidazolio)-propane sulfonates.

Liquid Chromatography - Mass Spectrometry of Zwitterionic Liquids

“…The second path is the formation of the ion B by the hydrogen transfer from the alkylsulfonate group to the nitrogen atom of the imidazole ring. Previous results obtained in deuterium exchange conditions show that the hydrogen transfer occurs from the protonated sulfonate group instead of migration of hydrogen atom from the alkyl chain [3]. The formation of the ion C is theoretically possible either from the ion A or the ion B by the same two paths described above.…”

“…Recently collision-induced dissociation (CID) of several imidazolium ZILs associated with the direct injection experiments have been carried out in our laboratory [3]. In addition, the fragmentation pathways of some S-and O-containig imidazolium ionic liquids were studied by positive Electrospray Ionization Fourier Transform Mass Spectrometry (ESI-FTMS) with Sustained Off-Resonance Irradiation (SORI) [4,5].…”

Electrospray ionization enters the final frontier: Mass spectrometry's role in understanding electrospray thrusters and their plumes

“…The two primary areas of relevance include (1) predicting thermal stability and thermal degradation pathways of ionic liquids as a function of the cation structure and (2) gaining new insights into the potential dissociation pathways and ultimate fate of the cations ejected into space. Typically without direct motivations relevant to spacecraft thrusters, several cation dissociation studies have been reported, including those investigating the dissociation of sulfur‐containing imidazoliums, imidazolium‐based zwitterions, and imidazoliums substituted with additional functional groups (e.g., alcohols, carboxylic acids, and iodobenzyls) . Given the ever‐expanding number of available cations, surely these ranks will continue to grow.…”

Study of Imidazolium And Pyrrolidinium Ionic Liquids By Ion Mobility Spectrometry And Electrospray Ionization Mass Spectrometry

“…Electrospray ionization mass spectrometry (ESI‐MS) is recognized as a suitable technique for the study of ILs. It has been used for the direct detection of intact ions of both undiluted and dissolved ILs, and for investigating their decomposition and fragmentation pathways . Conversely, ion mobility spectrometry (IMS) has been rarely utilized for investigations of ILs.…”

“…It has been used for the direct detection of intact ions of both undiluted and dissolved ILs, [4][5][6] and for investigating their decomposition and fragmentation pathways. [7][8][9] Conversely, ion mobility spectrometry (IMS) [10] has been rarely utilized for investigations of ILs. In general, IMS is used for the detection of chemical warfare agents [11] and explosives.…”