Počet záznamů: 1
Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines
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SYSNO ASEP 0462367 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Electrochemical and Quantum Chemical Study of Reactivity of Orthophthalaldehyde with Aliphatic Primary Amines Tvůrce(i) Donkeng Dazie, Joel (UFCH-W) RID, ORCID
Liška, Alan (UFCH-W) RID, ORCID
Ludvík, Jiří (UFCH-W) RID, ORCIDZdroj.dok. Journal of the Electrochemical Society. - : Electrochemical Society - ISSN 0013-4651
Roč. 163, č. 9 (2016), G127-G132Poč.str. 6 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova electrochemistry ; quantum chemical study ; amines Vědní obor RIV CG - Elektrochemie CEP GA13-21704S GA ČR - Grantová agentura ČR Institucionální podpora UFCH-W - RVO:61388955 UT WOS 000388988100106 EID SCOPUS 84982741535 DOI 10.1149/2.0451609jes Anotace The reactivity of orthophthalaldehyde (OPA) with primary amines is a base for broad application of OPA: in the determination of
amino acids, in medicine as a disinfection agent and in organic synthesis, therefore the detailed knowledge of the mechanism is of
interest. The electrochemical reducibility of OPA was utilized for the investigation of its reactivity with eight aliphatic primary amines
which could be separated into four types. Based on the electrochemical monitoring, the apparent reaction rates were evaluated. It
was found that the reaction rate essentially depends on the substitution at the α-carbon atom of the amine. The quantum chemical
computations revealed that the reaction rate well corresponds with the Hirshfeld and NBO atomic charges on the α-carbon atom.
Because of the strong hydration of OPA in aqueous solutions, the reaction was performed both in aqueous solutions (pH 9–10) as
well as in diethyl ether. For the identification of intermediates and products, NMR, MS and X-ray crystal structure analyses have
been used. Besides the expected isoindolin-1-one main products, the phthalimide derivative as a side product was observed and a
new type of the conjugate product has been found and identified. The plausible reaction pathway was proposed.Pracoviště Ústav fyzikální chemie J.Heyrovského Kontakt Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Rok sběru 2017
Počet záznamů: 1