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スシシールトライアルメタンメカノフォールの異質結合裂け

  • 0Adolphe Merkle Institute, University of Fribourg, Chemin des Verdiers 4, 1700 Fribourg, Switzerland.
Journal of the American Chemical Society +

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2021年11月4日

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Radical Formation: Homolysis 00:54

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

For example, HCl in solution cleaves into H+ and Cl− ions, where the chlorine atom takes both bonding electrons with it, leaving a naked proton....

Mass Spectrometry: Molecular Fragmentation Overview 01:20

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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...

Mass Spectrometry: Cycloalkene Fragmentation 00:54

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The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.

The reaction proceeds via the cleavage of two carbon-carbon bonds in the cycloalkene to yield ethene. The remaining part of the cycloalkene structure is a dienyl radical cation with a molecular weight of 28 u lower than the molecular ion. This fragmentation pathway is similar to the fragmentation of cycloalkanes releasing ethene, differing only in the resultant radical cation. An alkyl species...

Cycloaddition Reactions: MO Requirements for Thermal Activation 01:16

3.8K

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

The reaction occurs between the highest occupied molecular orbital (HOMO) of one π component and the lowest unoccupied molecular orbital (LUMO) of the other. These are...

Hybridization of Atomic Orbitals II 03:35

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sp3d and sp3d 2 Hybridization

To describe the five bonding orbitals in a trigonal bipyramidal arrangement, we must use five of the valence shell atomic orbitals (the s orbital, the three p orbitals, and one of the d orbitals), which gives five sp3d hybrid orbitals. With an octahedral arrangement of six hybrid orbitals, we must use six valence shell atomic orbitals (the s orbital, the three p orbitals, and two of the d orbitals in its valence shell), which gives six sp3d 2 hybrid...

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation 01:01

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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,...