4-Hydroxyphenacyl Ammonium Salts: A Photoremovable Protecting Group for Amines in Aqueous Solutions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F15%3A00081137" target="_blank" >RIV/00216224:14310/15:00081137 - isvavai.cz</a>
Result on the web
<a href="http://pubs.acs.org/doi/10.1021/acs.joc.5b01770" target="_blank" >http://pubs.acs.org/doi/10.1021/acs.joc.5b01770</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.5b01770" target="_blank" >10.1021/acs.joc.5b01770</a>
Alternative languages
Result language
angličtina
Original language name
4-Hydroxyphenacyl Ammonium Salts: A Photoremovable Protecting Group for Amines in Aqueous Solutions
Original language description
Irradiation of N-protected p-hydroxyphenacyl (pHP) ammonium caged derivatives at 313 nm releases primary and secondary amines or ammonia in nearly quantitative yields via the photo-Favorskii reaction when conducted in acidic or neutral aqueous buffered media. The reaction efficiencies are strongly dependent on the pH with the most efficient and highest yields obtained when the pH of the media maintains the ammonium and p-hydroxyl groups as their conjugate acids. For example, the overall quantum yields of simple secondary amines release are 0.5 at acidic pH from 3.9 to 6.6 dropping to 0.1 at neutral pH 7.0 and 0.01 at pH 8.4. Speciation studies provide an acid-base profile that helps define the scope and limitations of the reaction.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
The Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
80
Issue of the periodical within the volume
19
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
9713-9721
UT code for WoS article
000362386400034
EID of the result in the Scopus database
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