Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F16%3A00462367" target="_blank" >RIV/61388955:_____/16:00462367 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/16:10326311
Result on the web
<a href="http://dx.doi.org/10.1149/2.0451609jes" target="_blank" >http://dx.doi.org/10.1149/2.0451609jes</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1149/2.0451609jes" target="_blank" >10.1149/2.0451609jes</a>
Alternative languages
Result language
angličtina
Original language name
Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines
Original language description
The reactivity of orthophthalaldehyde (OPA) with primary amines is a base for broad application of OPA: in the determination ofnamino acids, in medicine as a disinfection agent and in organic synthesis, therefore the detailed knowledge of the mechanism is ofninterest. The electrochemical reducibility of OPA was utilized for the investigation of its reactivity with eight aliphatic primary aminesnwhich could be separated into four types. Based on the electrochemical monitoring, the apparent reaction rates were evaluated. Itnwas found that the reaction rate essentially depends on the substitution at the α-carbon atom of the amine. The quantum chemicalncomputations revealed that the reaction rate well corresponds with the Hirshfeld and NBO atomic charges on the α-carbon atom.nBecause of the strong hydration of OPA in aqueous solutions, the reaction was performed both in aqueous solutions (pH 9–10) asnwell as in diethyl ether. For the identification of intermediates and products, NMR, MS and X-ray crystal structure analyses havenbeen used. Besides the expected isoindolin-1-one main products, the phthalimide derivative as a side product was observed and annew type of the conjugate product has been found and identified. The plausible reaction pathway was proposed.
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
CG - Electrochemistry
OECD FORD branch
—
Result continuities
Project
<a href="/en/project/GA13-21704S" target="_blank" >GA13-21704S: Electrochemically active calix[4]arenes and their use for preparation of new receptors and (bio)sensors</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of the Electrochemical Society
ISSN
0013-4651
e-ISSN
—
Volume of the periodical
163
Issue of the periodical within the volume
9
Country of publishing house
US - UNITED STATES
Number of pages
6
Pages from-to
"G127"-"G132"
UT code for WoS article
000388988100106
EID of the result in the Scopus database
2-s2.0-84982741535