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Related Concept Videos

Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

5.2K
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...
5.2K
Mass Spectrometry: Aromatic Compound Fragmentation01:23

Mass Spectrometry: Aromatic Compound Fragmentation

2.3K
Upon ionization, aromatic compounds generate a molecular ion that is observed as a prominent peak in their mass spectra. For example, the molecular ion peak for benzene appears at a mass-to-charge ratio of 78, while toluene is observed at a mass-to-charge ratio of 92. The molecular ion benzene is highly stable and does not readily undergo further fragmentation due to the significant amount of energy required to disrupt the aromatic stability of the benzene ring. In contrast, the molecular ion...
2.3K
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

2.1K
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...
2.1K
Mass Spectrometry: Long-Chain Alkane Fragmentation01:18

Mass Spectrometry: Long-Chain Alkane Fragmentation

2.3K
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...
2.3K
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

1.4K
The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
1.4K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

3.0K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.0K

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Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
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Aromatic Fragmentation Based on a Ring Overlap Scheme: An Algorithm for Large Polycyclic Aromatic Hydrocarbons Using

Benjamin W Noffke1, Daniel Beckett1, Liang-Shi Li1

  • 1Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.

Journal of Chemical Theory and Computation
|March 3, 2020
PubMed
Summary
This summary is machine-generated.

A new computational method, Aromatic Fragmentation Based on a Ring Overlap Scheme (AroBOROS), accurately models large polycyclic aromatic hydrocarbons (PAHs) by breaking them into smaller, overlapping aromatic subsystems for precise calculations.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Physical Chemistry

Background:

  • Polycyclic Aromatic Hydrocarbons (PAHs) are crucial in various fields, but their accurate computational modeling is challenging.
  • Existing methods struggle with the size and complexity of large PAHs.

Purpose of the Study:

  • To develop a novel, systematic fragmentation scheme for accurate computational treatment of PAHs.
  • To improve the efficiency and accuracy of calculating properties for large PAHs and related systems.

Main Methods:

  • Developed the Aromatic Fragmentation Based on a Ring Overlap Scheme (AroBOROS) algorithm.
  • Generated overlapping biphenyl and naphthalene subsystems based on aromatic sextet rings.
  • Combined subsystems using Clar's rule to minimize energy and reduce errors.

Main Results:

  • Achieved accuracy below the chemical threshold for PAHs up to 84 carbon atoms.
  • Demonstrated effectiveness on diverse PAH test sets.
  • Validated the method on larger systems, including a 132-carbon nanotube fragment.

Conclusions:

  • AroBOROS provides a robust and accurate approach for modeling complex PAHs.
  • The fragmentation scheme effectively reduces computational errors, even for small fragments of large systems.