Ketonization of enols in aqueous solution: is carbon protonation always rate-determining?

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F12%3A00107106" target="_blank" >RIV/00216224:14310/12:00107106 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2012/pp/c2pp05369a" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2012/pp/c2pp05369a</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c2pp05369a" target="_blank" >10.1039/c2pp05369a</a>

Result language
angličtina
Original language name
Ketonization of enols in aqueous solution: is carbon protonation always rate-determining?
Original language description
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.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10608 - Biochemistry and molecular biology

Project
<a href="/en/project/ED0001%2F01%2F01" target="_blank" >ED0001/01/01: CETOCOEN</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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