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Carbon–hydrogen bond activation facts for kids

Kids Encyclopedia Facts

Carbon–hydrogen bond activation, or C-H activation, is a special type of chemical reaction that breaks a strong connection between a carbon atom and a hydrogen atom. This reaction often uses organometallic compounds, which are molecules that have a metal atom connected to carbon atoms.

In C-H activation, a hydrocarbon molecule (which is made of carbon and hydrogen) gets close to a metal atom. The metal helps to weaken and then break the bond between the carbon and hydrogen. This process is different from other reactions because the carbon-hydrogen part stays connected to the metal atom as the bond breaks.

Chemists study C-H activation because for a long time, they thought that C-H bonds were very hard to break. Now, both scientific theories and experiments show that these bonds can be broken. This happens when a nearby metal atom changes how the electrons are shared in the C-H bond.

A lot of chemical research focuses on making new chemicals and catalysts that can do C-H activation. The main goal is to turn cheap and common substances like alkanes (like methane or propane) into more valuable organic compounds that can be used to make medicines, plastics, or other useful materials.

History of C-H Activation

Historians say that Otto Dimroth found the first C-H activation reaction in 1902. He reported that benzene, a type of hydrocarbon, reacted with mercury(II) acetate. However, some scientists do not fully agree that this was the first true C-H activation.

Later, scientists Goldman and Goldberg explained that C-H activation is similar to how hydrogen-hydrogen (H-H) bonds are broken. Both can happen through processes called electrophilic or oxidative addition.

The first reaction that was widely accepted as a true C-H activation was reported by Joseph Chatt in 1965. In his experiment, a ruthenium atom, which was attached to other molecules called ligands, inserted itself into a C-H bond of naphthalene. This showed clearly that a metal could directly break and interact with a C-H bond.

See also

  • Oxidative coupling of methane

Images for kids

  • Cobalt C-H activation

    Cobalt-catalyzed C-H activation

  • Fujiwarachfunctionalization

    Fujiwara's palladium- and copper-catalyzed C-H functionalization

  • Figure 1. General scheme of a Murai reaction

    Murai reaction; X = directing group.

  • Sanford Figure 2 mechanism

    Mechanism for Pd-catalyzed C-H activation

  • Hartwig figure 1 borylation

    Hartwig borylation

  • Ru cat. borylation

    Ru catalyst based borylation

  • MethaneOxidationinH2SO4

    C–H Bond activation Periana 1998

  • AsymRh2DAcarbInsn

    Methyl phenyldiazoacetate is the precursor for asymmetric C-H activation via donor-acceptor carbene using a chiral dirhodium catalyst.

  • Natural Product Synth Ellman Figure 1

    Key step in synthesis of lithospermic acid

  • Mescalineprep

See also

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