Imidazolium salts with varying anions as charge carriers for detection of neutral bis(triphenylphosphine)palladium(II) dichloride in electrospray ionization mass spectrometry

Walton, Barbara L.; Joshi, Ubisha; Dzyuba, Sergei V.; Youngblood, W. Justin; Verbeck, Guido F.

doi:10.1002/rcm.6653

Cited by 5 publications

(4 citation statements)

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“…The most common RTILs are imidazolium, pyridinium, pyrrolidinium, and phosphonium-based organic salts . In previous ESI-MS studies, RTILs were used to increase the detection selectivity and sensitivity of analytes such as neutral polysaccharides or organometallic compounds because they could serve as good charge carriers. , ESI-MS was also used to analyze ionic liquids; , however, heated curtain/desolvation gas was required to reduce the sample viscosity, and the contamination to the mass spectrometer was often the major problem . In our experiment, [emim][BF 4 ], [bmpy][BF 4 ], [edmim][NTf 2 ], and [P 66614 ][TMPP], were chosen as representative examples for PESI test, using the regular probe (Figure a).…”

Section: Resultsmentioning

confidence: 99%

“…40 In previous ESI-MS studies, RTILs were used to increase the detection selectivity and sensitivity of analytes such as neutral polysaccharides or organometallic compounds because they could serve as good charge carriers. 41,42 ESI-MS was also used to analyze ionic liquids; 43,44 however, heated curtain/desolvation gas was required to reduce the sample viscosity, 43 and the contamination to the mass spectrometer was often the major problem. 44…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Development of Solvent-Free Ambient Mass Spectrometry for Green Chemistry Applications

2014

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Green chemistry minimizes chemical process hazards in many ways, including eliminating traditional solvents or using alternative recyclable solvents such as ionic liquids. This concept is now adopted in this study for monitoring solvent-free reactions and analysis of ionic liquids, solids, and catalysts by mass spectrometry (MS), without using any solvent. In our approach, probe electrospray ionization (PESI), an ambient ionization method, was employed for this purpose. Neat viscous room-temperature ionic liquids (RTILs) in trace amounts (e.g., 25 nL) could be directly analyzed without sample carryover effect, thereby enabling high-throughput analysis. With the probe being heated, it can also ionize ionic solid compounds such as organometallic complexes as well as a variety of neat neutral solid chemicals (e.g., amines). More importantly, moisture-sensitive samples (e.g., [bmim][AlCl4]) can be successfully ionized. Furthermore, detection of organometallic catalysts (including air-sensitive [Rh-MeDuPHOS][OTf]) in ionic liquids, a traditionally challenging task due to strong ion suppression effect from ionic liquids, can be enabled using PESI. In addition, PESI can be an ideal approach for monitoring solvent-free reactions. Using PESI-MS, we successfully examined the alkylation of amines by alcohols, the conversion of pyrylium into pyridinium, and the condensation of aldehydes with indoles as well as air- and moisture-sensitive reactions such as the oxidation of ferrocene and the condensation of pyrazoles with borohydride. Interestingly, besides the expected reaction products, the reaction intermediates such as the monopyrazolylborate ion were also observed, providing insightful information for reaction mechanisms. We believe that the presented solvent-free PESI-MS method would impact the green chemistry field.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Development of Solvent-Free Ambient Mass Spectrometry for Green Chemistry Applications

2014

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“…The analysis of various organometallic complexes by electrospray ionization mass spectrometry (ESI-MS) is often problematic due to their solubility in protic organic solvents. 221 Nevertheless, a neutral organometallic complex, bis-(triphenylphosphine)palladium II, was successfully analyzed by employing [C 4 MIM]-based ILs. The best sensitivities were obtained when employing more hydrophobic anions such as [BF 4 ], trifluoromethylsulfonate, and heptafluorobutanoate.…”

Section: ■ Mass Spectrometrymentioning

confidence: 99%

Ionic Liquids in Analytical Chemistry: Fundamentals, Advances, and Perspectives

et al. 2013

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“…[14][15][16] Furthermore, it is often used for protic and aprotic solvents. 17 The application of ESI-MS for the analysis of transition metal complexes was reviewed in Ref.…”

Section: Introductionmentioning

confidence: 99%

Soft Ionization of Metallo-Mefenamic Using Electrospray Ionization Mass Spectrometry

Abdelhamid¹,

Wu²

2015

Mass Spectrometry Letters

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Detection of mefenamic acid (M, non-steroidal anti-inflammatory drug, NSAIDs) and its metallodrug was investigated using electrospray ionization mass spectrometry (ESI-MS) and fluorescence spectroscopy. ESI-MS data (500 µL, 1×10-3 M) revealed high detection sensitivity for the drug and metallodrug. ESI-MS spectra revealed peaks at 242, 580, and 777 Da corresponding to [M+H]+, [63Cu(M-H)2(H2O)2+H]+, and [56Fe(M-H)3+H]+, respectively. The metal:mefenamic ratios of ESI-MS spectra are in complete agreement with the fluorescence spectroscopy results (1:2 for Cu(II) and 1:3 for Fe(III)). ESI is a soft ionization technique that can be used on labile metallo-mefenamic acids and is promising for the detection of these species in environmental samples and biological fluids.

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Imidazolium salts with varying anions as charge carriers for detection of neutral bis(triphenylphosphine)palladium(II) dichloride in electrospray ionization mass spectrometry

Abstract: A charge carrier for a neutral organometallic complex was found in imidazolium salts, where the cation was observed as the ionizing agent. Differing ion intensities of the complex-adduct peak resulted from the anions ability to dissociate from the cation.

Cited by 5 publications

References 36 publications

Development of Solvent-Free Ambient Mass Spectrometry for Green Chemistry Applications

Development of Solvent-Free Ambient Mass Spectrometry for Green Chemistry Applications

Ionic Liquids in Analytical Chemistry: Fundamentals, Advances, and Perspectives

Soft Ionization of Metallo-Mefenamic Using Electrospray Ionization Mass Spectrometry

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