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Related Concept Videos

Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

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The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can...
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Mass Spectrometry: Alcohol Fragmentation01:03

Mass Spectrometry: Alcohol Fragmentation

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Alcohols (R-OH) ionize to lose one non-bonded electron from the oxygen atom, forming molecular ions. Due to their tendency to fragment rapidly, the intensity of the molecular ion peak in the mass spectrum is weak or sometimes absent. The fragmentation patterns for alcohols occur in two ways, i.e. ⍺-cleavage and dehydration. During ⍺-cleavage, the bond at the ⍺-position adjacent to the hydroxyl group cleaves to give a resonance-stabilized cation and a radical. However,...
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Mass Spectrometry: Branched Alkane Fragmentation01:29

Mass Spectrometry: Branched Alkane Fragmentation

1.2K
This lesson delves into the mass spectrometry of branched alkane fragmentation. Branched alkanes possess secondary or tertiary carbon atoms, which generate relatively stable carbocations if the cleavage occurs at the branching point. The high stability of carbocations drives the instant fragmentation of branched alkanes. Accordingly, the branched alkane's molecular ion peak is very weak or invisible in the mass spectra, especially in comparison to a linear alkane.
1.2K
Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

Mass Spectrometry: Long-Chain Alkane Fragmentation

1.8K
The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
1.8K
Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation01:01

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

1.7K
The fragmentation patterns observed for compounds such as carboxylic acids, esters, and amides in the mass spectra include ⍺-cleavage and McLafferty rearrangement. Fragmentation by ⍺-cleavage preferentially occurs at the carbon-carbon bond at the ⍺-position next to the carboxylic group to generate a neutral radical and a cation. Long chain compounds with hydrogen at their γ-carbon undergo McLafferty rearrangement to give a radical cation and a neutral alkene.
For example,...
1.7K
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

1.6K
In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
For example, cyclohexane molecular ions have a mass-to-charge ratio (m/z) of 84, which tends to produce a stronger signal than linear alkanes like hexane. This stability comes from...
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Single-throughput Complementary High-resolution Analytical Techniques for Characterizing Complex Natural Organic Matter Mixtures
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Unsupervised Structural Classification of Dissolved Organic Matter Based on Fragmentation Pathways.

Dennys Leyva1, Muhammad Usman Tariq2, Rudolf Jaffé1

  • 1Department of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, United States.

Environmental Science & Technology
|January 4, 2022
PubMed
Summary

This study enhances the structural analysis of dissolved organic matter (DOM) using advanced mass spectrometry. It reveals complex DOM structures and potential biogeochemical transformations by mapping molecular connections.

Keywords:
DOMESI-FT-ICR MS/MScore fragmentnetworkneutral lossprecursor

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Area of Science:

  • Environmental Chemistry
  • Analytical Chemistry
  • Biogeochemistry

Background:

  • Dissolved organic matter (DOM) is crucial for Earth's ecological and biogeochemical cycles.
  • Determining the molecular structure of DOM remains a significant analytical challenge.
  • Previous methods offered limited insights into DOM structural signatures and reaction pathways.

Purpose of the Study:

  • To extend the structural characterization of wetland DOM.
  • To utilize precursor and fragment ions from tandem mass spectrometry for detailed analysis.
  • To identify and visualize structural families and potential biogeochemical processes within DOM.

Main Methods:

  • Employed sequential electrospray ionization-Fourier transform-ion cyclotron resonance tandem mass spectrometry (ESI-FT-ICR CASI-CID MS/MS).
  • Analyzed nearly 900 precursor and 24,000 fragment molecular ions within a specific m/z range.
  • Dissected DOM structure into families based on neutral mass loss patterns in 2D MS/MS space.

Main Results:

  • Identified over 1900 structural families of DOM compounds using precursor and neutral loss data (H2O, CH4O, CO2).
  • Revealed a high degree of isomeric content, often indistinguishable by precursor ion analysis alone.
  • Developed a connectivity map of structural families for visualizing DOM biogeochemical transformations.

Conclusions:

  • The integrated approach significantly enhances DOM structural characterization.
  • High-resolution mass fragmentation combined with computational tools provides deeper molecular insights.
  • The study visualizes potential biogeochemical processes influencing DOM throughout its lifecycle.