KLÍČOVÁ, Ľubica, Peter ŠEBEJ, Tomáš ŠOLOMEK, Bruno HELLRUNG, Petr SLAVÍČEK, Petr KLÁN, Dominik HEGER and Jakob WIRZ. Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution. Journal of Physical Chemistry A. USA: The American Chemical Society, 2012, vol. 116, No 11, p. 2935-2944. ISSN 1089-5639. Available from: https://dx.doi.org/10.1021/jp3011469.
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Basic information
Original name Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution
Authors KLÍČOVÁ, Ľubica (203 Czech Republic, belonging to the institution), Peter ŠEBEJ (703 Slovakia, belonging to the institution), Tomáš ŠOLOMEK (703 Slovakia, belonging to the institution), Bruno HELLRUNG (756 Switzerland), Petr SLAVÍČEK (203 Czech Republic), Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution), Dominik HEGER (203 Czech Republic, belonging to the institution) and Jakob WIRZ (756 Switzerland).
Edition Journal of Physical Chemistry A, USA, The American Chemical Society, 2012, 1089-5639.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher United States of America
Confidentiality degree is not subject to a state or trade secret
WWW URL
Impact factor Impact factor: 2.771
RIV identification code RIV/00216224:14310/12:00058036
Organization unit Faculty of Science
Doi http://dx.doi.org/10.1021/jp3011469
UT WoS 000301766500040
Keywords in English Photochemistry; p-Hydroxyacetophenone; Laser flash spectroscopy
Tags AKR, rivok
Tags International impact, Reviewed
Changed by Changed by: prof. RNDr. Petr Klán, Ph.D., učo 32829. Changed: 1/4/2015 22:16.
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, 3HA*, adiabatic proton transfer through solvent water simultaneously forms both the anion, 3A–*, and the quinoid triplet enol tautomer, 3Q*. The latter subsequently equilibrates with its anion 3A–*. Ionization and tautomerization are likely to compete with the desired release reactions of p-hydroxyphenacyl photoremovable protecting groups.
Links
ED0001/01/01, research and development projectName: CETOCOEN
GA203/09/0748, research and development projectName: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii
Investor: Czech Science Foundation, New photoactivatable compounds for organic chemistry and biology
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