Adiabatic triplet state tautomerization of p-hydroxyacetophenone in aqueous solution

The Journal of Physical Chemistry. a
Ĺubica KlíčováJakob Wirz

Abstract

The primary photophysical processes of p-hydroxyacetophenone (HA) and the ensuing proton transfer reactions in aqueous solution were investigated by picosecond pump-probe spectroscopy and nanosecond laser flash photolysis. Previous studies have led to mutually inconsistent conclusions. The combined data allow us to rationalize the excited-state proton transfer processes of HA in terms of a comprehensive, well-established reaction scheme. Following fast and quantitative ISC to the triplet state, (3)HA*, adiabatic proton transfer through solvent water simultaneously forms both the anion, (3)A(-)*, and the quinoid triplet enol tautomer, (3)Q*. The latter subsequently equilibrates with its anion (3)A(-)*. Ionization and tautomerization are likely to compete with the desired release reactions of p-hydroxyphenacyl photoremovable protecting groups.

References

Jul 13, 2006·The Journal of Physical Chemistry. a·Pavel LeidermanDan Huppert
Jul 15, 2006·The Journal of Physical Chemistry. a·Johannes NeugebauerCees Gooijer
Apr 10, 2010·The Journal of Physical Chemistry. a·Leszek LapinskiMaciej J Nowak
Aug 6, 2010·The Journal of Physical Chemistry. a·Yuval Erez, Dan Huppert
Feb 22, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Richard S GivensJakob Wirz
Feb 1, 2011·Canadian Journal of Chemistry·Richard S GivensJakob Wirz

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Citations

Mar 11, 2016·The Journal of Physical Chemistry. B·Amanda L HoukChristopher G Elles
Sep 18, 2015·Organic Letters·Tomáš SlaninaPetr Klán
Sep 17, 2015·The Journal of Organic Chemistry·Iwona BownikPetr Klán
Jul 7, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Bokolombe Pitchou NgoyPetr Klán
Jan 23, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jamaludin Al AnshoriPetr Klán
Nov 19, 2019·Frontiers in Chemistry·Bokolombe P NgoyTebello Nyokong
Aug 28, 2020·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Thomas FieldRichard S Givens
Oct 20, 2017·Chemistry : a European Journal·Edoardo TortiVladimir Sindelar
Jun 13, 2012·The Journal of Organic Chemistry·Viju Balachandran KammathRichard S Givens

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