Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/00216208:11310/16:10326311

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CG - Elektrochemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA13-21704S" target="_blank" >GA13-21704S: Elektrochemicky aktivní kalix[4]areny a jejich využití pro přípravu nových receptorů a (bio)senzorů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of the Electrochemical Society

ISSN

0013-4651

e-ISSN

—

Svazek periodika

163

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

"G127"-"G132"

Kód UT WoS článku

000388988100106

EID výsledku v databázi Scopus

2-s2.0-84982741535