Adiabatic Triplet State Tautomerization of
p-Hydroxyacetophenone in Aqueous Solution

J 2012

Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution

KLÍČOVÁ, Ľubica; Peter ŠEBEJ; Tomáš ŠOLOMEK; Bruno HELLRUNG; Petr SLAVÍČEK et al.

Základní údaje

Originální název

Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution

Autoři

KLÍČOVÁ, Ľubica; Peter ŠEBEJ; Tomáš ŠOLOMEK; Bruno HELLRUNG; Petr SLAVÍČEK; Petr KLÁN; Dominik HEGER a Jakob WIRZ

Vydání

Journal of Physical Chemistry A, USA, The American Chemical Society, 2012, 1089-5639

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.771

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/12:00058036

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1021/jp3011469

UT WoS

000301766500040

Klíčová slova anglicky

Photochemistry; p-Hydroxyacetophenone; Laser flash spectroscopy

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 1. 4. 2015 22:16, prof. RNDr. Petr Klán, Ph.D.

Anotace

V originále

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.

Návaznosti

ED0001/01/01, projekt VaV

Název: CETOCOEN

GA203/09/0748, projekt VaV

Název: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

Investor: Grantová agentura ČR, Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

Citovat

KLÍČOVÁ, Ľubica; Peter ŠEBEJ; Tomáš ŠOLOMEK; Bruno HELLRUNG; Petr SLAVÍČEK; Petr KLÁN; Dominik HEGER a Jakob WIRZ. Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution. Journal of Physical Chemistry A. USA: The American Chemical Society, 2012, roč. 116, č. 11, s. 2935-2944. ISSN 1089-5639. Dostupné z: https://doi.org/10.1021/jp3011469.

@article{1081098,
   author = {Klíčová, Ľubica and Šebej, Peter and Šolomek, Tomáš and Hellrung, Bruno and Slavíček, Petr and Klán, Petr and Heger, Dominik and Wirz, Jakob},
   article_location = {USA},
   article_number = {11},
   doi = {https://doi.org/10.1021/jp3011469},
   keywords = {Photochemistry; p-Hydroxyacetophenone; Laser flash spectroscopy},
   language = {eng},
   issn = {1089-5639},
   journal = {Journal of Physical Chemistry A},
   title = {Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution},
   url = {http://pubs.acs.org/doi/abs/10.1021/jp3011469},
   volume = {116},
   year = {2012}
}

TY  - JOUR
ID  - 1081098
AU  - Klíčová, Ľubica - Šebej, Peter - Šolomek, Tomáš - Hellrung, Bruno - Slavíček, Petr - Klán, Petr - Heger, Dominik - Wirz, Jakob
PY  - 2012
TI  - Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution
JF  - Journal of Physical Chemistry A
VL  - 116
IS  - 11
SP  - 2935-2944
EP  - 2935-2944
PB  - The American Chemical Society
SN  - 10895639
KW  - Photochemistry
KW  - p-Hydroxyacetophenone
KW  - Laser flash spectroscopy
UR  - http://pubs.acs.org/doi/abs/10.1021/jp3011469
N2  - 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.
ER  -

KLÍČOVÁ, Ľubica; Peter ŠEBEJ; Tomáš ŠOLOMEK; Bruno HELLRUNG; Petr SLAVÍČEK; Petr KLÁN; Dominik HEGER a Jakob WIRZ. Adiabatic Triplet State Tautomerization of p-Hydroxyacetophenone in Aqueous Solution. \textit{Journal of Physical Chemistry A}. USA: The American Chemical Society, 2012, roč.~116, č.~11, s.~2935-2944. ISSN~1089-5639. Dostupné z: https://doi.org/10.1021/jp3011469.

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