Formation of a Stable ‘Proton‐bridged Dimer’ by Decomposition ofCH
 3
 CH(OC
 2
 H
 5
 )CH(OC
 2
 H
 5
 )CH
 3
 +•
 in a Mass Spectrometer

Milliet, A.; Rempp, Muriel; Sozzi, G.

doi:10.1002/(sici)1096-9888(199607)31:7<749::aid-jms350>3.0.co;2-#

Cited by 3 publications

(2 citation statements)

References 19 publications

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“…For example, the deprotonated and covalently bonded dimer of gingerols [9], stable proton-bridged dimer of ethanol [10] or (2-oxooxazolidin-4-ylmethyl)carbamic acid tertbutyl ester [11]. All of them are mostly dimer ions identified both in the positive and negative ion mode, denoted as [2M + H] + or [2M − H] − .…”

Section: Introductionmentioning

confidence: 99%

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

et al. 2021

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Specific and nonspecific non-covalent molecular association of biomolecules is characteristic for electrospray-ionization mass spectrometry analysis of biomolecules. Understanding the interaction between two associated molecules is of significance not only from the biological point of view but also gas phase analysis by mass spectrometry. Here we reported a formation of non-covalent dimer of quaternary ammonium denatonium cation with +1 charge detected in the positive ion mode electrospray ionization mass spectrometry analysis of denatonium benzoate. Hydrogen deuterium exchange of amide and carbon-bonded hydrogens revealed that charge neutralization of one denatonium cation is the consequence of amide hydrogen dissociation. DFT (Density Functional Theory) calculations proved high thermodynamic stable of formed dimer stabilized by the short and strong N..H-N hydrogen bond. The signal intensity of the peak characterizing non-covalent dimer is low intensity and does not depend on the sample concentration. Additionally, dimer observation was found to be instrument-dependent. The current investigation is the first experimental and theoretical study on the quaternary ammonium ions dimer. Thus the present study has great significance for understanding the structures of the biomolecules as well as materials.

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Section: Introductionmentioning

confidence: 99%

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

et al. 2021

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“…The formation of the covalently bonded dimer adducts was dependent on the type of instruments used 8. A stable proton‐bridged dimer of ethanol was reported in the ion source of a Fourier transform ion cyclotron resonance (FT‐ICR) mass spectrometer 9. There has so far been no reported study on the MS n fragmentation behaviour of non‐covalent dimer ions for small molecules.…”

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confidence: 99%

A non‐covalent dimer formed in electrospray ionisation mass spectrometry behaving as a precursor for fragmentations

Pan

2008

Rapid Comm Mass Spectrometry

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A non-covalent-bonded dimer was detected in the positive ion electrospray ionisation (ESI) mass spectra of a synthetic impurity. In tandem mass spectrometry (MS/MS) experiments using collision-induced dissociation (CID), the ion was found to behave as a [M+H]+-type precursor ion for fragmentation until MS5. The dimer was probably formed through multi-hydrogen bonds over a proton bridge. When the fragmentation occurred at the center of the bridge, the dimer was broken apart to give monomer fragments at MS6. However, no corresponding deprotonated dimer [2M-H]- was found in the negative ion ESI spectra. The dimer was extremely stable, and it could still be observed when a fragmentation voltage of up to 50 V was applied in the ionisation source. The formation of the non-covalent dimer was also found to be instrument-dependent, but independent of sample concentration. Accurate mass measurements of the [2M+H]+ and [M+H]+ ions, and their MSn product ions, provided the basis for assessing the fragmentation mechanism proposed for [2M+H]+. The fragmentation pathway was also illustrated for the deprotonated molecule [M-H]-.

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Challenges in Applying Chemometrics to LC–MS-Based Global Metabolite Profile Data

Want

2009

Bioanalysis

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Metabolite profiling can provide insights into the metabolic status of complex living systems through the non-targeted analysis of metabolites in any biological sample. Metabolite profiling is complementary to genomics, transcriptomics and proteomics, and its applications span epidemiology, disease diagnosis, nutrition, pharmaceutical research, and toxicology. Metabolic phenotypes are a reflection of an organism's environment, lifestyle, diet, gut microfloral composition and are also influenced by genetic factors, with important implications in genome-wide-association studies. Specialized analytical platforms, such as NMR spectroscopy and MS, are required to interrogate such metabolic complexity. The increased sophistication of such techniques has lead to a demand for improved data analysis approaches, including preprocessing and advanced chemometric techniques. This article discusses data generation, preprocessing, multivariate analysis and data interpretation for LC-MS-based metabolite profiling, focusing on challenges encountered and potential solutions.

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Formation of a Stable ‘Proton‐bridged Dimer’ by Decomposition ofCH ₃ CH(OC ₂ H ₅ )CH(OC ₂ H ₅ )CH ₃ ^+• in a Mass Spectrometer

Cited by 3 publications

References 19 publications

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

A non‐covalent dimer formed in electrospray ionisation mass spectrometry behaving as a precursor for fragmentations

Challenges in Applying Chemometrics to LC–MS-Based Global Metabolite Profile Data

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Formation of a Stable ‘Proton‐bridged Dimer’ by Decomposition ofCH 3 CH(OC 2 H 5 )CH(OC 2 H 5 )CH 3 +• in a Mass Spectrometer

Cited by 3 publications

References 19 publications

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

A Non-Covalent Dimer Formation of Quaternary Ammonium Cation with Unusual Charge Neutralization in Electrospray-Ionization Mass Spectrometry

A non‐covalent dimer formed in electrospray ionisation mass spectrometry behaving as a precursor for fragmentations

Challenges in Applying Chemometrics to LC–MS-Based Global Metabolite Profile Data

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Product

Resources

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Formation of a Stable ‘Proton‐bridged Dimer’ by Decomposition ofCH ₃ CH(OC ₂ H ₅ )CH(OC ₂ H ₅ )CH ₃ ^+• in a Mass Spectrometer