Adiabatic triplet state tautomerization of p-hydroxyacetophenone in aqueous solution |
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Authors: | Klíčová Ĺubica Šebej Peter Šolomek Tomáš Hellrung Bruno Slavíček Petr Klán Petr Heger Dominik Wirz Jakob |
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Affiliation: | Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00 Brno, Czech Republic. |
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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. |
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