Polarographic Determination of Phthalaldehyde

Furman, N. H.; Norton, D. R.

doi:10.1021/ac60091a003

Cited by 19 publications

(19 citation statements)

References 12 publications

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“…The products from the reaction of phthalaldehyde and ammonia in MeaSO depended on the initial concentration of aldehyde. While phthalimidine (4a) was produced in high yield in dilute Me2SO solutions, more concentrated solutions yielded 3-(2-cyanophenyl)isoquinoline (5) and a dark polymer with a consequent decrease in the yield of 4a. The structure of 5 was inferred from the following considerations: (1) IR showed a -CN; (2) NMR showed nine aromatic protons and a tenth at 9.29 ppm, characteristic of the proton in the 1 position of isoquinoline; and (3) its mass spectrum.…”

Section: Resultsmentioning

confidence: 99%

Reactions of phthalaldehyde with ammonia and amines

Minh¹,

Johnson²,

Jones³

et al. 1977

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Reactions of phthalaldehyde with ammonia and amines

Minh¹,

Johnson²,

Jones³

et al. 1977

J. Org. Chem.

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“…3) after the reduction wave 2 can be a sign of a catalytic process. In the case of phthalaldehyde, both forms, free and monohydrated, are reducible [39]. Benzaldehyde can be reduced to benzyl alcohol in one two-electron step [40,41].…”

Section: Resultsmentioning

confidence: 99%

On reduction of the drug diflunisal in non-aqueous media

et al. 2015

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The electrochemical reduction of diflunisal was studied in dimethyl sulfoxide on static mercury drop electrode. Diflunisal yields one irreversible wave at -1.2 V (vs. Ag | AgCl | 1 M LiCl electrode) due to the reduction of the carboxylic functional group in the molecule. The electrochemical properties of the drug were compared with the ones of the chlorinated analogue. The study is based on cyclic voltammetry, tast polarography, and constant potential electrolysis. The experimental findings are supported by molecular orbital calculations. The mechanism of reduction of the carboxylic moiety was found to involve two electrons and two protons. The reduction pathway leads to formation of an aldehyde derivative. Graphical Abstract

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“…The use of this technique for determination of equilibrium constants of reactions of various carbonyl compounds with primary amines was reported early. 5 The decrease of polarographic waves of OPA in the presence of amino acids and ammonia was used early for analytical purposes, 6 but the nature of the processes involved was not elucidated.…”

Section: Introductionmentioning

confidence: 99%

Reactions of orthophthalaldehyde with ammonia and 2-aminoethanol

Kulla

Zuman

2008

Org. Biomol. Chem.

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Reactions of orthophthalaldehyde (OPA) with amines are used in the determination of amino acids and in applications of OPA as a biocide. To contribute to the understanding of processes involved, the reactions of OPA with ammonia, which are conveniently slow, were studied. In a set of rapidly established equilibria, the 1,3-dihydroxyindole and the product of its dehydration are formed (Scheme 1). The individual equilibria were identified and equilibrium constants determined using DC polarography and UV spectra. The ring closure involves the carbinolamine; the imine formation is a side reaction. Both the ring formation and the dehydration of the carbinolamine are generally acid catalyzed. In the finally established overall equilibria between OPA and the isoindole derivative, the concentrations of intermediates are negligible. The same applies to the reaction of OPA with 2-aminoethanol, in which the initial formation of a carbinolamine and of an imine are too fast to be followed. Very slow reactions taking place during periods of hours or days, which probably result in the formation of dimeric species, have also been observed. This contribution demonstrates the advantages of combinations of polarographic and spectrophotometric techniques in the investigation of complex reactions of some organic compounds.

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Polarographic Determination of Phthalaldehyde

Cited by 19 publications

References 12 publications

Reactions of phthalaldehyde with ammonia and amines

Reactions of phthalaldehyde with ammonia and amines

On reduction of the drug diflunisal in non-aqueous media

Reactions of orthophthalaldehyde with ammonia and 2-aminoethanol

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