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@article{1597503,
author = {Pelliccioli, Anna Paola and Šebej, Peter and Wirz, Jakob},
article_location = {CAMBRIDGE},
article_number = {6},
doi = {http://dx.doi.org/10.1039/c2pp05369a},
keywords = {KETO-ENOL; DISSOCIATION-CONSTANT; BUFFER SOLUTIONS; ACID; HYDRATION; SYSTEM},
language = {eng},
issn = {1474-905X},
journal = {PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES},
title = {Ketonization of enols in aqueous solution: is carbon protonation always rate-determining?},
url = {https://pubs.rsc.org/en/content/articlepdf/2012/pp/c2pp05369a},
volume = {11},
year = {2012}
}
TY - JOUR
ID - 1597503
AU - Pelliccioli, Anna Paola - Šebej, Peter - Wirz, Jakob
PY - 2012
TI - Ketonization of enols in aqueous solution: is carbon protonation always rate-determining?
JF - PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
VL - 11
IS - 6
SP - 967-971
EP - 967-971
PB - ROYAL SOC CHEMISTRY
SN - 1474905X
KW - KETO-ENOL
KW - DISSOCIATION-CONSTANT
KW - BUFFER SOLUTIONS
KW - ACID
KW - HYDRATION
KW - SYSTEM
UR - https://pubs.rsc.org/en/content/articlepdf/2012/pp/c2pp05369a
L2 - https://pubs.rsc.org/en/content/articlepdf/2012/pp/c2pp05369a
N2 - The pH-rate profiles for the ketonization of the (E)- and (Z)-photoenols of o-methylacetophenone (MA) in aqueous solution were determined by nanosecond laser flash photolysis. Carbon protonation of the enol anions of MA by solvent water is exceptionally fast, k(0)'K approximate to 2.0 x 10(7) s(-1), too fast to permit establishment of the acid-base equilibrium on the enol oxygen prior to ketonization. Analysis of the pH-rate profile of the (E)-enol using the common assumption of rate-determining carbon protonation would lead to an erroneous value for the acidity constant of that enol, pK(a,c)(E) = 11.3, which is too high by about two pK units.
ER -
PELLICCIOLI, Anna Paola, Peter ŠEBEJ a Jakob WIRZ. Ketonization of enols in aqueous solution: is carbon protonation always rate-determining? \textit{PHOTOCHEMICAL \&{}amp; PHOTOBIOLOGICAL SCIENCES}. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2012, roč.~11, č.~6, s.~967-971. ISSN~1474-905X. Dostupné z: https://dx.doi.org/10.1039/c2pp05369a.
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