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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 occur at...
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Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

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The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
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Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation01:01

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

2.6K
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,...
2.6K
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

2.3K
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...
2.3K
Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

Mass Spectrometry: Long-Chain Alkane Fragmentation

2.5K
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...
2.5K
Mass Spectrometry: Alkyne Fragmentation00:53

Mass Spectrometry: Alkyne Fragmentation

2.1K
The fragmentation of alkynes preferentially occurs at the carbon–carbon bond between the α and β carbon of the alkyne bond to generate a 3-propynyl cation (or propargyl cation). In terminal alkynes, there is the only type of fragmentation that yields the 3-propynyl cation. The unsubstituted 3-propynyl cation exhibits a peak at a mass-to-charge ratio of 39. In internal alkynes, the 3-propynyl cation is substituted. For example, 2-pentyne fragments into methyl-substituted...
2.1K

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Workflow and Tools for Crystallographic Fragment Screening at the Helmholtz-Zentrum Berlin
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C-C fragmentation: origins and recent applications.

Michael A Drahl1, Madhuri Manpadi, Lawrence J Williams

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854 (USA).

Angewandte Chemie (International Ed. in English)
|October 12, 2013
PubMed
Summary
This summary is machine-generated.

This review traces the origins of carbon-carbon bond fragmentation reactions, highlighting recent advances in methods and applications for synthesizing complex molecules.

Keywords:
alkenesalkynesallenesnatural productssynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • The archetypal C-C bond fragmentation reaction was disclosed 60 years ago.
  • Numerous variations, including Beckmann, Grob, Wharton, Marshall, and Eschenmoser-Tanabe fragmentations, have been developed.
  • A comprehensive review of the origins and evolution of fragmentation reactions is lacking.

Purpose of the Study:

  • To trace the historical origins of C-C bond fragmentation reactions.
  • To summarize recent advancements in heterolytic C-C fragmentation methods over the past 20 years.
  • To highlight the applications of these fragmentation reactions in synthesizing complex molecular structures.

Main Methods:

  • Historical literature review focusing on the origins of fragmentation reactions.
  • Analysis of new fragmentation methodologies developed in the last two decades.
  • Examination of case studies demonstrating applications in natural product synthesis.

Main Results:

  • The review provides a historical perspective on the development of C-C fragmentation reactions.
  • It details recent innovations, particularly in fragmentations yielding alkynes and allenes.
  • Successful applications of these reactions to diverse and complex molecular motifs are presented.

Conclusions:

  • Heterolytic C-C fragmentation reactions have evolved significantly over 60 years.
  • Recent methods offer powerful tools for constructing complex organic molecules.
  • Continued exploration of fragmentation reactions promises further synthetic utility.