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What is the mechanism of trialkylborane oxidation with hydroperoxide?
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What is the mechanism of trialkylborane oxidation with hydroperoxide?
One aspect is the release of the stable anion $\ce{OH-}$.
Another aspect is that $\ce{B-O}$ bonds are much stronger than $\ce{B-C}$ bonds because the empty p-orbital of boron overlaps with one p-orbital with a lone electron pair of oxygen.
values taken from “Bond Dissociation Energies”, in CRC Handbook of Chemistry and Physics, 90th Edition (CD-ROM Version 2010), David R. Lide, ed., CRC Press/Taylor and Francis, Boca Raton, FL.
One aspect is the release of the stable anion $\ce{OH-}$.
Another aspect is that $\ce{B-O}$ bonds are much stronger than $\ce{B-C}$ bonds because the empty p-orbital of boron overlaps with one p-orbital with a lone electron pair of oxygen.
values taken from “Bond Dissociation Energies”, in CRC Handbook of Chemistry and Physics, 90th Edition (CD-ROM Version 2010), David R. Lide, ed., CRC Press/Taylor and Francis, Boca Raton, FL.
One aspect is the release of the stable anion $\ce{OH-}$.
Another aspect is that $\ce{B-O}$ bonds are much stronger than $\ce{B-C}$ bonds because the empty p-orbital of boron overlaps with one p-orbital with a lone electron pair of oxygen.
$\ce{B-C}$ $D_{298}^ \circ = 448 \pm 29\ \mathrm{kJ\ mol^{-1}}$
$\ce{B-O}$ $D_{298}^ \circ = 809\ \mathrm{kJ\ mol^{-1}}$
values taken from “Bond Dissociation Energies”, in CRC Handbook of Chemistry and Physics, 90th Edition (CD-ROM Version 2010), David R. Lide, ed., CRC Press/Taylor and Francis, Boca Raton, FL.
One aspect is the release of the stable anion $\ce{OH-}$.
Another aspect is that $\ce{B-O}$ bonds are much stronger than $\ce{B-C}$ bonds because the empty p-orbital of boron overlaps with one p-orbital with a lone electron pair of oxygen.
$\ce{B-C}$ $D_{298}^ \circ = 448 \pm 29\ \mathrm{kJ\ mol^{-1}}$
$\ce{B-O}$ $D_{298}^ \circ = 809\ \mathrm{kJ\ mol^{-1}}$
values taken from “Bond Dissociation Energies”, in CRC Handbook of Chemistry and Physics, 90th Edition (CD-ROM Version 2010), David R. Lide, ed., CRC Press/Taylor and Francis, Boca Raton, FL.
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